Thursday, November 27, 2008

He is walking around with an ass full of my cum today.......

As I said in a previous post, I really missed cherryboi over the last few weeks. We spoke every day and sometimes more than once, but it's not the same as seeing his pretty face light-up when we are together. He has been back and we spent the last 5 days together before he left again yesterday to spend Thanksgiving with his family. I sent him home to his Mother with an ass full of my cum. I am sure she won't have a clue. cherryboi plays the straight young son very well apparently and the saga goes on.

Blogging is a tough thing. Originally, I started this Blog because I didn't know anyone in DC and was dealing with the abundance of opportunities that seemed to present themselves for connections in this town. For me, DC has been pretty much a sexual smörgåsbord. Almost from day one, there has been a chance to get-off or get laid whenever I was really looking for one. I have even had a lot of chances when I wasn't looking. I have written about some of these and not written about others. Sometimes I have struggled with what to write and what not to write. I have even written about a few things that I regretted writing about later. I look at that as part of sharing. Some of you read this Blog for the sex and the hook-up stories and I know from e-mails that some of you read it becaise you seem to be interested in me and my life too.

So that brings me to what really are two different points that I wanted to make: 1) Some times I am not making updates to this Blog because I am struggling with what to write and what not to write and I am torn about it. Should I just post the hot encounters that I have or should this Blog be a dairy of every time I have sex? I have struggled with this and don't have the answer yet. 2) Feelings? Do I post about what and how I feel or should this Blog just be a chronicle of how and where I shoot my load? I am working my way through these conflicts.

So, here are some feelings. cherryboi has become very important to me. I feel myself headed down a road that I was actively attempting to avoid. It just feels good when we are together. The problems: 1) He is still very closeted. My friends know him and he is part of my life at my place, but I am just a "friend" in his life. He plays straight. This isn't a complaint. It is really a concern. If he isn't totally comfortable in his own skin am I foolish to try to build something with him? 2) I am 40. He is 26. WTF does this beautiful young man want with me?

Happy Thansgiving to all! I am preparing to go to a get-together at my friend "Dan"'s house.

Saturday, November 15, 2008

Been away for a while....

I am fine. I still have a job. I can say that has been touch-and-go recently. The balance in my retirement accounts tells me that I am going to be working somewhere a long time. But, things are good, I have a job!

I have hardly seen cherryboi in more than 6 weeks. At the beginning of October, he headed back to his Congressman's district to work on the campaign. The election was apparently suddenly close. Good news is that the Congressman won re-election. Bad news is that I really really miss him. This is something I have only come to actively recognize the last few weeks. We speak every day, but I miss him. So the saga of cherryboi goes on, more later.

The Cop only left a few hours ago. I got home late on Friday and crashed early. Around 3AM, my phone rings and it is The Cop. "Can I come over after my shift ends?", he asks. "Yeah", I say. "The door will be unlocked.".

I woke up early this AM to a very sensuous massage and blowjob. It was long and easy. He worked my shoulders a while and then sucked me for a few minutes. He moved to another body part and the cycle went on until I blew a big creamy load all over his scruffy face. I fell back asleep and woke up a few hours later to find this perfectly formed man freshly-showered sleeping beside me. I have always been amazed a my luck in finding The Cop. He is all man. He is 100% prime beef. Each part of his body is perfectly formed and defined. For some reason he keeps coming back and he is completely submissive with me. I have learned over time that I can have him anyway I want. It is unsaid, but never resisted. He submits to everything I want to do. This morning we fucked and sucked and fucked some more. Afterwards, I made a small brunch for us to eat and then he left. Damn, I hope he calls again!

I had something really nice happen on the Metro Friday morning. I got on the train at the New York Avenue Station and immediately noticed that K was on the same car. This has been happening again lately. I quickly put my iPod ear buds in and tried to zone. And, I noticed Him. You know how some guys just look incredibly good in their jeans? I noticed Him several weeks ago. On Friday's, he wears jeans that just hang on him perfectly. You can see the definition of his calves and the firmness of his tight bubble butt. It's also impossible to miss his package hanging there. He has caught me looking I know, so yesterday I was more discreet in my glances. So, I rode downtown trying to ignore K and not glare at His crotch. At Gallery Place, the doors opened and He moved closer to me as he moved toward the doors to exit. When he was right beside me, he leaned in and said, "Hello, my name is D" and handed me a card. I am waiting for a return call....

Monday, September 29, 2008

Gareth Redux Pt. 2

Gareth and I had a lot of sex. We had a lot of great sex. We had sexy virtually everyday we were together. We fell into a real nice rhythm. I had several days of meetings in Munich. I'd leave in the morning and return early in the afternoon to find Gareth waiting in the room with a plan for the evening and a suggestion on where to eat. We would go see or do some tourist thing or just walk around the city from platz to platz. I have been to Munich before. I have gotten very used to traveling alone, but it was so nice to not be alone and to see things through another's eyes and to just have company. He was really great company too. It was really comfortable between us very quickly. We talked about everything.

Each night, we would come back to the room and have passionate sex. Gareth is a total bottom, but not submissive in any way. He likes to be fucked and luvs cock, but always preferred to be on top riding my cock. I remembered that this was how we fucked last year and soon realized it was his preference. He was often aggressive during sex about wanting to end up riding my cock. I was happy to accommodate. Unlike a lot of bottoms, he has a talent for controlling and flexing his ass. He would use his ass to almost massage me to orgasm. He is an incredibly well built and handsome young man. I enjoyed lying back having my cock milked by his tight ass while I enjoyed his body with my hands. I quickly learned that he was hard-wired to his small brown nipples. I would work his nipples and almost be able to control how he rode my cock with them. It was erotic and very hot. The after sex was comfortable and lingering. We often went at it all night. The lingering memory of cuddling with him and sleeping against him was how fresh and good he smelled. One day, I finally asked him about his scent and he laughed in his English-way and said it was his soap. He uses this sandalwood soap that he "got at home", as he would say.

We made our way from Munich to Firenze and then on to Rome. We kept up the same rhythm of me working, sight-seeing, dinner and fucking. I started to feel real guilty because he seemed to be staying in the room all day, when I had work meetings etc. One day as I was preparing to leave I said, "Go out and have some fun. You are in Rome." He smiled the most endearing smile and softly replied, "I am have a great time with you, Mate."

As quickly as we were meeting up in Frankfurt, I was standing in Rome's Leonard da Vinci Airport trying to figure out how to say goodbye. I had too good of a time with Gareth. It was too comfortable and I almost ached that we were parting again. He was emotional too. It wasn't my imagination. He had a hard time evening talking or looking at me. We hugged hard. We kissed a few times. I made him promise to think about a trip to the States. He made me promise to work hard on getting a client in England. I whimsically thought about how nice it would be to have him come home with me.....

Wednesday, September 17, 2008

Gareth Redux Pt. 1

As I Blogged earlier, I was in Europe from August 8th through August 27th, mostly in Germany and Italy. It was a work trip again this year. I have two projects at work that are European-based. I started planning the trip in June and immediately starting maneuvering by e-mail to meet up with Gareth while I was there.

If you have been reading this Blog for a while, you will remember that Gareth is the major fucking hot English lad that I met on a train to Milan last year. We spent two days and nights together in Milan and I have always regretted that it wasn't long. We have gone back and forth by e-mail since last year and chatted about him visiting the US, but that never happened. Gareth was anxious to meet up and had the entire month of August open. So Saturday, August 8th, as I came out of Customs at Franfurt International Airport, a tall, tanned and and handsome Gareth was standing in the crowd wearing a great big smile.

He greeted me very affectionately and we shared a few long lingering kisses. I had an instant charge from how warm his welcome was and I was really glad to see him. He was every bite as hot as the first time I glimpsed him on the train platform. He hadn't changed at all. He was still a hottie with a tight-fitting polo shirt and khaki slacks accenting his broad shoulders and "british" prep look. We fell in together and headed to the S-Bahn to catch a train to Frankfurt Central Train Station - Frankfurt (Main) Hbf. By the time we were seated on the S-Bahn, it was almost like we had never parted ways in Milan last year. 20 minutes later, we were eye'ing each other while we waited in line to by tickets to Munich. An hour after that, we were locked in the WC as the train rolled toward Munich and I pounded Gareth's tight ass. I was embarassed how fast I shot my load in his ass. The condom didn't reduce the sensation of his tight hole and round ass against me. Immediately, I got on my knees to finish him off. I couldn't resist his magnificent uncut cock. He didn't last long either. I could feel his hands come to the back of my head and I could hear his breathing get deeper and soon I had a mouthful of creamy salty cum. I don't suck cock that often. I am not sure thsat I am any good at it and most bottoms seem to want cock in their assess more than head. I couldn't resist the chance this time. I stood up and started to kiss Gareth. He was shocked that my mouth was still full with his load. As we kissed, I pushed part of his load into his mouth. It was very intimate and hot! Tasting of him, I think we kissed and savored his seed longer than we fucked

End of Part 1.

Wednesday, September 03, 2008

A Really Nice Sleepover

I heard from The Married Guy last week that his wife would be out of town over Labor Day Weekend. I haven't hooked up with him in a long while. I enjoy The Married Guy both in and out of bed. He is a very engaging and outgoing guy. He has this boyish charm that verges on cockiness. I'd be crazy not to want to fuck him and at the same time I enjoy just hanging with him and watching a soccer game too. He wanted to drop by on Saturday or Sunday and I chose Sunday.

He was at my door promptly at 7:00PM. He was dressed in a pair of tan cargo shorts and a Washington Nationals t-shirt and was carrying a six-pack of beer. I let him in and as I turned from closing the door, I was met with a deep passionate kiss. Clearly, The Married Guy seemed to have missed me too. I guess I reacted in some way, because he was quick to ask if everything was "OK?" I assured him everything was more than OK.

Clothes were off and we were in my room in no time. The Married Guy is a great kisser and we made out and groped at each other for a long time. During a brief break, he asked if he could spend the night. This was a first and took me by complete surprise, but I was quick to say yes. The Married Guy has this very appealing body. I love to watch him and I am always amazed by the combination of leanness and muscle definition. He is firm and smooth and soft against me and it feels good. I sucked on his nipples and licked his abs and worked my way down to his cock. He was freshly showered and smelled good. Being a little aggressive, I flipped him over on his stomach and went at his round smooth ass. He was very clean and had a sweet spicy taste. From the noises he made and the way his body reacted, I could tell he was into how I was rimming and eating his ass. I have eaten him occasionally in the past, but this time we had plenty of time and I took full advantage of the opportunity to make every muscle in his legs and on his taunt back twitch. He started to groan and murmured, "Fuck me." I kept eating. Then he more loudly asked me to, "Please fuck me!" I kept eating. Finally, he started to beg me, "Please fuck me! Oh, please fuck me!" I couldn't resist any longer, so I put on a condom and slowly started to work my cock into his ass using only my spit as lube. He is always very tight and it took a while to work the head of my cock in past his pucker, but the sensation of his tightness on my cock was well worth the effort. I could feel him adjusting as I worked in deeper with each thrust. Soon, I was balls deep in his ass. I let him adjust to the full length and girth of my cock and then I started a slowly fuck him. By this point, we both were covered in sweat. We went at it for a while with me mounting him from behind. Then I flipped him on his back and drug him to the edge of the bed, so I could really pound his ass. Now I was in a zone, but as I finished the look on his face told me that he was loving it and the hand full of jizz I had from stroking him was proof that he was satisfied.

We fucked again before we fell asleep wrapped around each other. And, we fucked again before I made some breakfast for us the next morning. It was a really nice sleepover.

I got a text message from The Married Guy asking if we could do it again soon. What do you think I replied?

Saturday, August 30, 2008

Posers - Go to Hell!

A lazy Saturday. cherryboi is out-of-town. We haven't actually seen each other for almost 3 weeks between his political shit back in the Congressman's district and the political convention and my more than two weeks in Germany and Italy. I will try to write about my trip soon. I have been on the run most of this month. I don't even have the much energy to look for some head or ass this afternoon.

This is redundant, but posers on-line are really bizarre to me. As anyone who reads this Blog knows, when I am bored and/or cherryboi isn't around I am usually cruising for sex. A few weeks ago I was on Manhunt, when I got chatted up by guy. Nothing too out of the ordinary about that. His profile was bare and he had no pics. There are a lot of profiles on Manhunt with no pics. It usually means the guy is married or a kid playing around - just my experience. Well after a few weeks of back and forth, the guy e-mails me a pic. I am impressed.

Since he now had my e-mail, he started to IM me on a regular basis. As always, I am a sucker for an eager bottom and I love to hear how good my cock looks. One thing leads to another and the guy announces that his wife is out of town this weekend. Long story short, he was supposed to call at 4:00PM today. Needless to say, he was a no show/no call. I checked his Manhunt profile a few minutes ago and it was deleted. His e-mail is now bouncing back too.

It is just utterly unbelievable the extent that these posers go. Why waste their time, not to mention everyone else's? I hope he has blisters from working himself.

Friday, July 11, 2008

Drumroll, Please - Test Results

I blurted out the offer to get tested from a combination of feeling cornered and fear. Admitting that, it was a sincere offer, though, and I fully intended to get tested with cherryboi as soon as we returned from the Outer Banks. cherryboi didn't bring it up again and schedules and travel for both of us got in the way. Soon 2 weeks had passed and we were into the 3rd week. On one of our regular nightly conversations, I mentioned to cherryboi that I was going to the Clinic to get tested the next day.

Immediately, the lawyer/political operative part of cherryboi's personality kicked in. Even the tone of his voice changed as he informed me, "I called and we have to go together to get tested and counseled to get our results at the same time."

Me: "You called and checked this out?"

cherryboi: "Yeah, I called the day after we got back from the beach and we have to go together to get tested and counseled to get our results at the same time."

Me: "Why didn't you say anything before now?"

cherryboi: "I thought you might have changed your mind."

Me: "I didn't change my mind. I almost went and surprised you. When do we go?"

We went together the Thursday before the 4TH of July. We both left work early and had no trouble getting into the Clinic for testing. We were in an out in about an hour. It was tremendously important to cherryboi. He showed it in his attitude, his body language and how tightly he insisted on holding my hand while we waited on the wooden benches at the Clinic.

The Results - we a both HIV-negative. This was not a surprise for me, but it was a noticeable relief to cherryboi. I promised him to return in 6 months as advised by the counselor. He must have professed his love for me a half a dozen times through the rest of the day. He also made a big deal out of thanking me while we were riding the Metro back to New York Avenue.

When we got back to my place, I was introduced to a totally new side of cherryboi - the aggressive bottom. It was straightforward and totally out of left field. As I reclined in a chair reading my Blackberry, he brought me a drink, stood in front of me and stripped all his clothes off, knelt and pulled my cock out of my pants and proceeded to suck me. It didn't take long for him to get me rock hard. Then he was all over me. While rubbing his tight young ass on my cock, he straddled my lap and tugged my shirt off and we began to make out.

With only his spit and my precum as lube, he soon had worked his tight ass around my cock. I know that it hurt him, but the friction from his tight ass on my cock was perfect. I could feel his tight little smooth ass against my thighs, against my balls and riding up against my cock as he ground himself against me. At the same time, he was passionately sucking my face and whispering complements into my ear about how much he liked and enjoyed my cock. The boy was fucking me and I liked it! Up to this moment, I had always fucked him. In no time, I was in the zone and realized that soon I wouldn't be able to stop myself from shooting my load into him. I whispered to him to slow down for a minute and he said, "No, I want your load in me now!" And with that it was! Six or seven large spurts and I was spent. It was a powerful orgasm from the friction and the eroticism of cherryboi being aggressive.

He continued to kiss me passionately and express his love for me and my seed. My cum as lube had enabled him to take more of me. I was balls-deep in his incredible ass. He started to work his hips and slide up and down on me. The stimulation from my cum and his tight ass around my cock kept me fairly hard. He rode me for a while. We would make out for a while and he would ride me for a while again. In between, we had snippets of a conversation and it was clear that he was now much more comfortable being my cumhole. His words. And with that, he began to encourage me for another load. Not much encouragement was require. This beautiful young man riding my cock and pleading for me to seed his ass, was more than enough encouragement. Soon more of my cum was swimming in his guts and his cum was all over my stomach and chest.

Later that night I had my cumhole again for a third load. This time I was the aggressor and I took the boy to show him he was mine.

Things are good right now! As I blogged before, I am not good at the dynamics of a relationship and I am working on that. For those of you blasting me for abusing cherryboi, I am seriously trying not to abuse him. He met me on a Craigslist post. He knew I was out there fucking, because he came to my house to get fucked. I was worried that it would become a choice between us and sex at some point, but apparently that won't happen for now. I made promises to cherryboi and I plan to keep them.

Will I continue to fuck? Hell yeah, I will. When I have cherryboi, I'll fuck him. When I am horny and he is not available, I'll look around and see what opportunities present themselves. For perspective, I think cherryboi needs to get out there and get fucked. I doubt a future with me as the only cock he ever takes. Right now, he totally dismisses that. He won't feel that way forever. So, should I give up sex now only to discover that this beautiful young man discovers the joys of being a hot young bottom in the future? No, I don't want him to resent me anymore than I want to resent him. If I am lucky, he does really love me. If this is a mature lasting relationship, one day when I have him bent over and I sense that he is now reacting differently to being fucked because the last guy in had a different style I will enjoy the variety and not feel threatened. I don't want cherryboi to be threatened by any of my hook-ups. I am 39, soon to be 40. cherryboi is 26. We are in different places in the journey of life. I don't want to be a bitter old Queen, because I lost a younger partner. I am trying to be realistic about a relationship with a young closeted gay man finding his way.

Thursday, July 03, 2008

Thugboy is in the DC Jail

Weird update on one of my regular cocksuckers. I called Thugboy twice early in June and I was deposited directly into voicemail. I left my normal generic message and oddly didn't hear back from him. Usually, I get an eager response the same evening or the next day.

Monday night, I gave it another try. I came home and was in the mood for some nsa head. I got Thugboy's voicemail again.

Tuesday evening, my cell rings and it is Thugboy.

Thugboy: "Ya lookin for me?"

Me: "Yeah. You know why."

Thugboy: "I'm locked up right now. My lawyer says I be here for a little while."

Me: "How did you get my message?"

Thugboy: "My family brought me my calls. They has my phone."

Me: "Well, I guess you are out of commission for a while. Be safe, Dude."

Thugboy: "I'm locked up right now, but I be out. We cool after that?"

Me: "We are cool."

After I ended the call, I began to wonder. I can see Thugboy being very busy in a jail environment. I imagine that the ragging hard-on I get putting this thug on his knees will make him very popular in jail. Probably lost one of my cocksuckers, because it may be too risky to keep him.

I called The Kid for some relaxed relief, since I needed some uncomplicated head. Within an hour his fresh face was buried in my crotch. I have a soft spot for this kid lately. It is always "Sir", when we talk. Also, he goes into a whimpering trance when he gets into blowing me that is very fucking erotic. I also have a The Kid sighting in a social situation that I am conflicted about disclosing on this Blog. But, since that sighting The Kid and I are a little bonded mainly from his gratitude that I didn't out him or know him giving discreet cover for him to play along.

Sunday, June 29, 2008

cherryboi and me, the saga goes on.............

I haven't posted in more than a month. Things have been crazy professionally, but in my personal life things have been going very well. I have been out of town a lot for work - Pittsburgh, Richmond, Raleigh-Durham and Atlanta. I have spent more than a week in Atlanta on two different occasions. cherryboi
was in DC finishing up law school for the spring term. We have fallen into this habit of texting back and forth through the day and if we aren't together, we end the day with a phone call. He is my boyfriend and things have been going well.

I don't do the relationship thing very well, I have noticed. Too may years by myself? Too pessimistic from years of disappointment? cherryboi says that he cares and he does all the right things to show that he cares, I wait for the next shoe to drop. Sometimes I hunt for trouble where there is none and make it when I can't find it, I think.

On the Thursday evening of my last trip to Atlanta, I had just gotten back to my hotel room and was thinking about what to do for dinner when there was a knock at my door. I opened the door to find cherryboi standing there with a big smile and an a bag slung over his shoulder. We ended up playing, sucking and fucking for the next 3 days. It was a very pleasant surprise and in a whole bunch of ways brought us even closer. While we were laying in each other's arms on day 2, I mentioned what a pleasant surprise it had been for him to just hop a plane and come down to see me. cherryboi gave me a big kiss and said, "I missed you and I wanted to be sure you were fucking me this weekend." He looked at me tenderly for a long time and we both knew what he was saying. I avoided taking him up on the topic. Then he said, "You know that I love you." I think for the first time, I really believed he might truly love me. It felt good!

Fast forward to Memorial Day Weekend, I decided that cherryboi and I should go away for the weekend. At my recommendation, we ended up at the house I stayed in last summer in Corolla in the Outer Banks. We drove down and took our time getting there. We went down on Thursday before Memorial Day and came back Tuesday after. It's not going to make for hot reading, but it was nice. We spent time on the beach and roaming around the Outer Banks. Took a guided tour of the rugged areas north of Corolla to see the wild horses. We fucked every night and again leisurely in the morning. We spent time cooking and drinking wine. We also finally had "the conversation".

Saturday night, cherryboi made a lemon and seafood pasta dish from a recipe he got from Rachel Ray on the Food Channel. I put together a salad and found two good bottles of wine. We kicked back on the deck overlooking the Atlantic with some candles and enjoyed a very relaxed dinner. We talked about us. cherryboi talked about politics and what his schedule with the Congressman will be this fall. He was so extremely cute trying to feel me out about whether it bothers me that he needs to travel a lot for work this fall. Then came the trap. I am not sure if it was the wine or three days of enjoying his tight ass, but before I knew what was coming he changed topic and starts:

cherryboi: "We need to talk about something. I have tried to bring this up several times, but I always chicken out. I am almost afraid to bring this up tonite, but I need to know something."

Me, gulping for air: "What?"

cherryboi: "Besides me, who else do you fuck bareback?"

It was hard to see his face in the candle light. The fact that he couldn't see my face may have been the only reason that he felt comfortable enough to ask this time. There was almost a child-like quality to his voice. I instantly felt anxious and almost scared.

Me, after a long pause: "What do you want me to say?"

cherryboi: "Let me talk before you say anything. Ok? We fuck bare. Don't get me wrong, I luv it. I really luv it. But, it's not like it was a mutual decision, You wanted to fuck bare and we do. Just please be honest with me. I am scared and I need to know where we stand with this."

Me: "You are the only guy I am fucking bare."

There was a really long period of silence. All I could hear was the pounding of the surf. I deliberately broke the silence.

Me: "You know, I got very lucky. I answered an ad on Craigslist and the guy turned out to be this incredible young man. I was just out of a rocky relationship and I was looking to get laid. I ended up finding this incredibly attractive, intelligent and accomplished guy who is becoming my friend and happens to be a very giving lover and hot piece of ass."

cherryboi: "What about that guy K?"

Me: "What about him?"

cherryboi: "God, I sound desperate. I ran this conversation over and over in my head and I did not want to sound desperate."

Me: "It has been over with K since before we met. I am not seeing him or fucking him."

cherryboi: "I know you are with other guys. I have known it all along. In the beginning of our relationship, I just wanted a relationship with you. I was confused about how I felt about me, about being with a man and about being gay, so I didn't really think about the other guys you might be with. I focused on trying to convince you that I was serious about us. At the same time, it was kinda hot that you had choices and chose me. Then after a while, I started to think that there were other guys because there was something I wasn't satisfying for you. I think I realize that other guys you are with have nothing to do with me or I try to convince myself of that. Now, I am just scared. You are in me. We use no protection and I have no idea how much risk I am taking."

My heart was pounding. It was pounding hard enough that I could hear the pulses in my eardrums over the surf.

Me: "Look this is going to sound like a cliche, but what we do and the intimacy we share is making love. With other guys, it is random sex. I was HIV- on my last test and that was more than a year ago. (Back when I was fucking Anonymous Fuck in Virginia, but I didn't share this with cherryboi.) When we get back home, you and I should both go together to the Whitman-Walker Clinic in the Dupont get tested."

cherryboi: "You will do that for me?"

Me: "Yes. And for what it is worth, I am aware that fucking you bare is a risk. I wouldn't deliberately expose you to more risk by exposing you to other guys. I have not been fucking anyone else bare. I promise you that. If you feel coerced by me to fuck bare, we need to stop now."

cherryboi: "That's the problem. I am conflicted and scared, because I don't want to stop. I want to be yours totally. But, I want one other promise."

Me: "Ok, what's that?"

cherryboi: "Promise that you won't fuck anyone else bare and promise not to fuck anyone that we know.

It seemed like 2 promises, but I promised without a comment or hesitation.

Me: "We can both live by those ground rules."

cherryboi: "You know that I love you. I don't want anyone else."

Me: "When you do I understand."

cherryboi: "I won't."

This young man's love is something wonderful and scary for me. It is completely unconditional and unselfish. I doubt that I deserve it, but it feels so GOOD!

Sunday, April 27, 2008


When I started to write this entry in the Blog, I went back and checked and I have not written about K since last November. I have studiously avoided him in life as I have in writing about him here. I still hear from him and see him on the Metro occasionally. He is still a beautifully handsome man. We talk on the Metro and his messages and texts me occasionally. He is still a damaged soul and it is unfortunate. I feel that my unwillingness to deal with his issues has quite possibly damaged him more and that pains me.

K knows that I am with cherryboi. We bumped into him at Gallery Place several weeks ago. He was leaving as we were arriving to see a movie. I am not trying to exaggerate, but I thought he was going to cry. There was such a pained look on his face when the realization came to him that I was with someone. I was put in a position where I had to introduce cherryboi to him. I explained to cherryboi over Häagen-Dazs after the movie that K and I had dated before he and I had met. I didn't go into a lot detail, but K's reaction was jarring enough that it came up after the movie.

cherryboi: "Who exactly is K?"

me: "We dated before I met you. It didn't work out and it's over."

cherryboi: "Does he know it's over?"

me: "If he is listening to what I have said to him over the last few months, he knows."

cherryboi: "He acted like he just caught his boyfriend out with another guy."

me: " He bumped into a guy he used to date with a hot young new boyfriend. Frankly, I am not sure I would have reacted much better seeing him with someone new after I broke it off with him."

cherryboi: "Do you still fuck him?"

I looked into cherryboi's eyes waiting for the next question as I said: "No, I don't fuck him anymore." The next question didn't come and he seemed to loose interest in K as a topic of conversation.

I received a long rambling e-mail from K several days later. He cares for me. It hurts to know that someone else is with me. yada yada yada. Then he offered that I could have him whenever I wanted, even though I had a boyfriend. I didn't respond to his messages, but each one was slightly more irrational than the last.

The whole experience made me numb. I'd like to say that I don't care about K, but that would be a lie. Seeing him react to cherryboi was uncomfortable. The emotions in his e-mails afterward were unsettling. There are still feelings there.

Friday, April 18, 2008

The Cop

The Cop has still been calling and dropping by on a fairly regular basis. The last two times he called before this last Monday evening, I have had to brush him off. Monday he called in the late afternoon and we arranged for him to drop by after 8:00PM. When he arrived with some wine and a big smile on his face, I told him we needed to chat.

The long and short of our chat was my coming clean that I am in a relationship with a new guy - cherryboi. I explained to him that this was the reason for the brush-offs recently. cherryboi has class on Monday's, so the coast was clear. The Cop was totally unconcerned. It turns out he has a "girlfriend" that he is seeing too. I wasn't shocked, but I was surprised. This dude is a total sub when my cock is in him. The Cop was frank with the explanation that he is closeted and plans to remain that way. He seemed concerned that I was planning to discontinue our hook ups. I am not planning to stop hooking up with him at this point. Let's be honest. I am feeling a tinge of guilt, but not enough to commit to monogamy yet. I get off on fucking a very hot cop.

So, the wine led to more wine and some cheese. We started messing around on my living room couch. The wine and messing around led to some poppers and my hands clamped on the The Cop's head fucking his face. Soon, I was straddling his face on the floor aggressively feeding him my cock. He was taking every thrust. I'd give him some air to breathe every few minutes and dangle my balls over his face for him to lick and suck. Then I'd ease my cock back into his mouth and start working it down his throat. He was taking it like a champ. After a few reps of alternating between feeding him my cock and then my balls, I cupped my ball sac in my hand and road up and pushed my ass crack into his face. I didn't give him a choice and soon I could feel his tongue exploring my crack and darting at my hole. It was tentative, but it was a start. I figure I'll explore rimming with my cop another time. I pulled back and presented him with my cock again and he gulped it back down. The blowjob had lasted long enjoy that my cock was incredibly sensitive to every sensation at this point. I could feel a load building to the point of no return. It occurred to me at this point that The Cop had never officially taken my load in his mouth. He always seemed to pull off in the end or end up with my cock in his ass. In this position, he didn't have much choice. As I was ready to blow, I eased my cock deeper into his mouth and put my hand on the back of his head to hold him on. I shoot a big load of cum into his mouth and down his throat. With the first big spurt I could feel his head try to move away, but I held him firmly. There were 4 or 5 more large spurts, but I held him firmly and did not let him pull off. He half choked or maybe half gagged, but he swallowed it all. I started gently thrusting again working my now softer cock in and out of his mouth. I could feel his tongue licking my soft cock. I wanted him to savor the taste. It was the first of many loads that he will take.

When we had recovered, we headed upstairs to my bedroom. Once in bed we messed around some more. Soon, I had The Cop on his back at the edge of the bed with his legs pushed up beside his head and me standing along the bed slamming my cock into him. After sucking my cock, drinking my load and messing around, he was totally horned. The harder I slammed my cock into him the more he moaned and bucked his hips and clawed at the bed covers. His cock was like stone and the head was coated with pre-cum. I wrapped my fist around the wet head of his cock and began stroking him as I fucked him. Suddenly, he grabbed handfuls of the bed covers and literally screamed out as his 8-pack abs. I shot a second time almost immediately. The clenching of his ass around my cock as he came finished me off.

Sunday, March 30, 2008

"That Was Amazing..... Thanks Dude!"

DC dies during any holiday. The combination of Spring Break last week with the Easter Holiday this past weekend made this City like a tomb. No one actually seems to live here or to be from here, so everyone de-camps anytime there are a few days off from school/work.

So being bored and horny on a Saturday night, I was cruising on Manhunt and checking out Craigslist. Half on a lark and half because of the attached picture, I responded to the following post from a guy in MD:

Trying agian (sp)

I tried last weekend, but couldn't find the right guy. I'm 23 yr old 6'4" 215 lbs. I just want to get dressed up for you. Suck you off, give you a lapdance, maybe fuck you. I've got a very tight ass, I think you'll love it. Be white, in shape and have pics to trade...looking for tonight!

I responded to this post with my stats and a picture.

Trying agian: You've got me fucking like the idea of me in a thong giving you a lapdance?

me: yeah! i'd luv to feed you my cock too.

Trying agian: You've got a great cock...i would love to suck on it...and rub my ass all over it.

me: hell yeah! now i'm hard!

Trying agian: Do you want to take care of that for you? When can you get here?

I have to say the pictures that Trying agian shared with me were incredible! In the pictures was a strapping and solid young white guy wearing a light blue thong. The guy in the pictures had a full meaty ass with a lean full torso. He didn't appear cut, but he had a solid muscular build.

Trying agian was in Maryland about 25-30 minutes from me. He needed to be discreet and needed to host. He stressed the need to be very discreet several times. We worked out the details and I headed out to meet him.

I had some difficulty finding the non-descript apartment complex along a road I was not familiar with in Maryland, but shortly before the appointed time I was rolling into the parking lot in front of the apartments. I soon found the right garden-style apartment and knocked on the door.

Trying agian opened the door and let me into the apartment. He was standing behind the door. When the door closed, there he was wearing black fishnet stockings that came up past his knees and the same light blue mesh thong he had been wearing in his pictures. He seemed anxious and almost paced around the room. Taking the initiative, I asked where he wanted to play. He pointed to a couch along the side of the room. As I was striping down to my boxers, I asked him what he was looking for. He asked me to sit down on the couch and wasted no time in peeling my boxers off. He was mesmerized by my cock and balls. He looked at them, felt them and squeezed them at one point before putting his head down into my crotch and taking the end of my cock into his mouth. He twirled his tongue around the head of my cock holding it and watching it grow in front of his face. I finally reached down and pushed his head down on my dick and he started to give me a very respectable blowjob. He lost himself sucking my cock and licking my balls for a good 5 minutes. Then he stopped and sheepishly asked if I would rub my cock on his ass.

With my cock wet from his mouth, I moved Trying agian around, pull his thong to the side and started to rub my cock along his smooth ass crack. He responded immediately to the sensation of my cock along his crack and against his hole. He started to thrust his hips working his crack against the shaft of my cock. It felt great to me too. Trying agian had a fresh soap smell and his hard young muscled back was flexing as he worked his crack on my cock. The harder he rubbed himself into my cock the more apparent it was to me that what he really wanted was my cock in his ass.

"Want me to fuck you?", I asked. "Can I ride it?", Trying agian replied. "Sure.", I responded.

Trying agian stood up and pulled his thong off. His smooth tight meaty ass was right in from of my face as he bent over to get out of this thong. I had an urge to eat it, but focused on fucking him for now. He kneeled down between my legs and fumbled with a condom while he gently tried to wrap my cock. I moved his hands aside and finished the job. He handed me some lube and I applied some to me and worked some into his crack. Then I let Trying agian lower himself onto my cock. I could immediately tell that he was tight. I had a hand on each hip guiding him down and immediately sensed him pull away and heard him gasp out loud as he felt the girth of my cock opening up his pucker. I held him firmly by his hips and told him to be still for a minute and relax. He was breathing heavy and I could feel his ass clenching and unclenching around the head of my cock as he adjusted to me being inside him. I hit the shaft of my cock with some more lube and slowly pulled him down on my cock. I felt his pucker open and my cock slide the rest of the way in. He started to ride my cock and was almost immediately into it. He was tight and the pressure of his tight ass sliding up and down on my shaft was incredible. He found his grove and was soon riding my cock like a champ. I laid my head back on the couch, kneaded his ass with my hands and enjoyed the zone, Soon, quicker that I wanted, I felt the pressure building in my groin. I knew I was close to the point of no return.

"I am going to nut in your ass!", I exclaimed. "Yeah man. Do it.", he grunted.

With that I reached around and clasped my hand around the shaft of his cock and began to stroke him. In less than a half a dozen strokes, he blew his load into my hand and I rubbed his cum all over his cock and down over his balls as I blew my load onto his tight ass.

Trying agian jumped up and returned with a towel for me to clean up with. He looked me directly in the eye and exclaimed, "That Was Amazing..... Thanks Dude!".

Saturday, March 22, 2008

Not Out............. Pt. 2

cherryboi being closeted is not a gigantic issue for me. It may possibly be an obstacle in our relationship, but it is not a big issue. I was just blindsided by it. I should not have been surprised, but I was caught by surprise. While I was getting the full court press from him, it never occurred to me. Under the circumstances, I should have realized that he is just discovering who he is. I think I have been focused on seeing how mature he has been while trying to enter a relationship with me. cherryboi is very smart and very mature, but I think a lot of the "maturity" is more posturing for my benefit than confidence with who he is as a gay man.

But, cherryboi and I are OK. When he got back into town last week, I made a point of having a long conversation with him. He is really totally closeted. It may be possible that the only people who know he is gay are the 3 guys (1 being me) that he claims to have hooked up with. He immediately moved to assure me that he is going to come out to everyone very soon. I could see how emotional this made him in his eyes and on his face as he spoke and I could tell that he saw this as a big issue for us. I told him that he shouldn't come out for any reason other than to satisfy himself. I made him promise me that he would do this thoughtfully and only when he was totally comfortable and ready.

cherryboi being closeted is not a gigantic issue for me. It may possibly be an obstacle in our relationship, but it is not a big issue. I was just blindsided by it. I should not have been surprised, but I was caught by surprise. While I was getting the full court press from him, it never occurred to me. Under the circumstances, I should have realized that he is just discovering who he is. I think I have been focused on seeing how mature he has been while trying to enter a relationship with me. cherryboi is very smart and very mature, but I think a lot of the "maturity" is more posturing for my benefit than confidence with who he is as a gay man.

But, cherryboi and I are OK. When he got back into town last week, I made a point of having a long conversation with him. He is really totally closeted. It may be possible that the only people who know he is gay are the 3 guys (1 being me) that he claims to have hooked up with. He immediately moved to assure me that he is going to come out to everyone very soon. I could see how emotional this made him in his eyes and on his face as he spoke and I could tell that he saw this as a big issue for us. I told him that he shouldn't come out for any reason other than to satisfy himself. I made him promise me that he would do this thoughtfully and only when he was totally comfortable and ready.

Before I get barraged with e-mails again, I do know that we were all in the closet at some point in our lives. I also believe that cherryboi has to be ready to come out and that he should only come out for himself. It can't be about me. We all have our own stories and most of us have scars from finding acceptance and from not finding acceptance from people.

So, what's next? I don't know as I write this. I guess we take it one day at a time, as "Dan" recommended to me. cherryboi is worth it, "Dan" argues. I agree. cherryboi is worth it. So as we take it one day at a time, you can probably read about it here.

Friday, March 21, 2008

Not Out

cherryboi is closeted. This is not a judgment. I am not sure it surprises me. I think that the evidence was there and I just didn't notice it. I don't know that I even care, at the moment. cherryboi is in the closet.

I was invited to an "intimate" birthday party that a friend of mine threw for his partner. "Howard" is a partner in a big DC law firm. "Dan" and "Howard" have been together for about 10 years. They have a fantastic loft apartment in the U Street neighborhood. Lots of stainless steel and glass with a great view of downtown DC. "Dan" is a really sweet guy that I met about week 2 after I moved to DC. We have never hooked-up, but we are very friendly and have fallen into a get together and telephone kind of friendship. If "Howard" is out-of-town or busy working, we will end up grabbing a bite to eat or hanging on the telephone or im'ing each other. "Dan" is a good guy that had a really shitty life until he and "Howard" found each other. "Dan" talked me through all the emotions and bs I went through with K. "Dan" also was a major cheerleader in my seeing the possibility that cherryboi could be more than a hook-up. While I was venting and pondering the whole cherryboi-thing, "Dan" confided to me that he and "Howard" had met in a club in SE DC that no longer exists in 1998. What used to be a gay nightclub district off of South Capitol Street has been transformed by the construction of a baseball stadium for the Washington NationalsWashington Nations. "Dan" was on his knees in the entry way to the bathroom sucking a guy's cock and when that guy shoot his load, "Howard" stepped up and took his place. At the end of the night, "Dan" was in a cab headed back to "Howard"'s place. They have been together ever since. "Howard" is 15 years "Dan"'s senior. By "Dan"'s logic, if he and "Howard" can build a relationship after a random bj in a bathroom then cherryboi and I are destiny. Anyway..............

When I invited cherryboi to the dinner party, I noticed a little bite of hesitation. He knows "Dan", so he ended up seemong to be more enthusiastic and nothing more was said. Fool that I sometimes can be, I didn't really think about it much. On the Metro headed over to the party he was quiet. There were a total of 4 other couples at the party, which was very fancily catered. We all drank far to much wine and there was a very broad running conversation about everything under the sun from politics to the bizarreness of the human condition. It didn't take long to realize that cherryboi was not at ease. He was not totally withdrawn, but he seemed quiet and pre-occupied. "Dan" finally rescued him from some good-natured teasing and they headed into the kitchen to fix everyone a nightcap as the evening was breaking up. We drank the nightcap and said our goodbyes.

Walking back to the Metro, I offered an apology that he didn't enjoy the evening. He brushed my apology aside with one of his own and offered that he just wasn't himself tonite. Rough week and he blamed working hard, etc. Nothing more was said. As we left the Metro at New York Avenue, we said our goodnight and parted ways. That was Thursday before last. cherryboi was on the road for work that weekend. Back to the Congressman's District with some kind of political event to attend.

So, the next Monday I call "Dan" to thank him for a great evening. In the course of the conversation, "Dan" lets me know that cherryboi is not "out". "Didn't you know?", he asks. Long story short, I didn't think about it but I guess I should have known.

Sunday, March 02, 2008

Where Things Are...............

For all of you who seem so focused on cherryboi being here when I got home on Valentine's Day. He doesn't have a key of his own, but he does know where I keep the spare and he has used it. I am not sure what message that sends him. I haven't offered a key and he hasn't asked for one. I think I am OK with that and I am not seeing a big issue.

I admit not a little bite of confusion over where things are with cherryboi. I started my last Post a day or so after Valentine's Day. When I originally started that Post, my first thought was that I should change how I am referring to him in this Blog. cherryboi is a nervous shy young lad who had his cherry taken on my rug downstairs. I pondered for a few days how I should refer to him in this Blog and that led to some real soul-searching on my feelings toward him. I definitely have feelings for him, but they are all tied up in him being a young lad who enjoyed and still seems to enjoy being taken by me. That's when it occurred to me that to have a real relationship with him, I have to let him be what he wants to be and he has to get what he is looking for out of this relationship. I think I have a tendency to idealize potential relationship situations with an image of how I think they should be instead of how they are. cherryboi liked having his cherry taken on my rug. He certainly came back for more. In many ways, the reason he is coming back has a lot to do with the feelings that created for him. So, I am gonna be me and I am just gonna enjoy him.

Now, I am gonna let the dog in me out for you all to see. For about a month, I have been chatting with this guy who has claimed to be a Marine stationed at the Washington Marine Barracks. We have exchanged e-mails and he has found me through a pic on my profile on Manhunt, so he has hit me up on there from time to time too. Frankly, I have been skeptical about the Marine claim, but he has great pics with a "USMC" tat on his bicep and a bulldog on his shoulder blade. Long story short, we have been chatting and he has been chasing me quite literally to fuck him for a while. Last Saturday night shortly after 10PM, he IM's me and asks, "wanna fuck me tonite?" I said WTF and gave him my address and jumped into the shower to freshen up.

About 40 minutes later, the Marine is standing at my door. He had to be close to 6'4" tall. He was wearing bluejeans and a leather jacket. He had the trademark "high and tight" haircut. This fag is a Marine. I invited him in and gave him a place to throw his jacket. I offered a beer, which he took me up on immediately. When I got back with the beer, he was standing in the middle of the room ramrod straight wearing a tight white t-shirt. I was almost ready to pinch myself.

We bs'ed and drank the beer. He was a friendly southern boy with a Texas drawl. Seemed like a no nonsense kind of a guy. He made a point of telling me that he was glad we were finally meeting. He had been wanting to meet me for a while. While I was wondering why this adonis wanted me, I thought there was no way I was not fucking this guy while I had the chance. I got up and said, Follow me, Lets go upstairs."

By the time we got to my bedroom, I made up my mind to be totally in charge and cocky about it. I told him to get undressed in a firm voice and watched as he disrobed. Words cannot describe his body. It was stunning like the statue of David. His pictures in no way captured the perfection of his form. He had a tall lean swimmers build. He had no fat anywhere that I could see. He was literally 100% chiseled muscle. He was nearly hairless and had perfectly smooth white skin. The only imperfections I saw were his tats. When he turned to face me I could see he was sporting a very nice cock crowned with a small lite brown bush above it and a pair of large low hanging balls under it. He had a young very healthy ageless appearance. He claims to be 30.

I crawled up on my bed and spread my legs. I looked at the Marine and said, "I wonder what it feels like to get blown by a Marine?" Without a word in reply, he jumped onto the bed between my legs and took my cock into his mouth. He quickly showed me that he was an expert cocksucker. He licked and nibbled eagerly at the head of my cock. Then he began working the shaft of my cock into his throat. Moving intensely up and down the shaft swallowing more with each bob of his head. Almost instantly, I was in a zone and really enjoying the sensation of this eager mouth on my cock. When I added the visual of this perfectly shaped man who happened to be a Marine to the equation, it was shear perfection. A few minutes into a great BJ, the Marine asked if I was Ok with him doing some poppers.

I don't do poppers often, but I will admit they push me to a different level during sex. At times in my life, the rush from poppers has scared me. In addition to intensifying the stimulation I get from sex, poppers make me last forever. I took a big hit and laid back to be pleased. This Marine literally worshipped and sucked my cock for 45 minutes without missing the beat. I was over the top most of the time from the pleasure of his mouth devouring my cock. I moaned and gasped in between exclamations of pleasure and tirades of calling him a "filthy cumwhore" and taunting him to do it longer and better.

Finally, I felt my load building in my groin. I ordered him to get on all fours and while I wrapped and lubed, I fingered his tight hole. I wasn't gentle. With one hand on the small of his back bracing my weight and the other guiding the shaft of my cock, I forced my way into him. He screamed out a pained, "Shit!", but squirmed to adjust. I held back until I felt the flexing of his pucker subside. Then I just fucked him. A few minutes from behind, a minute or so in the scissor position and then finally drove it home while he held his knees back and exposed his ass to me. He was there meeting every thrust and begging for more. As I was building to shoot my load, he begged me to shoot it on him. I pulled out, tore the condom off and held the base of my cock and hosed him with my cum. I came in strings and shot all over him from his chin to his bush. There were 6 to 8 large squirts that had more force than I normally shoot with. I impressed myself!

We laid side my side for a few minutes as we both caught our breathe. Then he slowly started to stroke and I slide back down to eat his hole. He immediately blew his load and mixed it with mine all over him.

I never dreamt I would find a Marine bottom!

Friday, February 29, 2008

Valentine's Day

This may not be the post that anyone wants to read. I am on my way to becoming domesticated. cherryboi made a big deal out of Valentine's Day. He started about 10 days before reminding me to save the day for us. It was really very endearing and I started to get into it. I got the royal treatment.

I got a call from cherryboi at about 4:00PM on Valentine's Day reminding me not to work late. We had plans he reminded me yet again. When I got home, he was already at my place - cooking. Taking the cue from how he was acting, I had some flowers, a bottle of wine and a book that I thought he would enjoy to give him. He was all smiles and seemed genuinely touched that I made the effort to choise the book that I choose.

He made a complete dinner. I had no idea he could even cook. There was an incredible salad dressed with a raspberry dressing with walnuts and parmesan cheese chopped over it. He made a very tasty seafood pasta dish and chose a very mellow and dry white win to go with it. We relaxed and ate and chatted and flirt for 2 and a half hours over dinner. We polished off 2 bottles of the win. On top of being hot and young, he is very smart and engaging. I thought it was a very nice evening. It was only the beginning.

After dinner, he led me upstairs and helped me undress. I crawled up on the bed, somewhat high from the amount of wine I had consumed. He stripped down and crawled between my legs and proceeded to worship, tease and edge my cock for one of the best blowjobs I have ever had. As I came, he stared up at me and swallowed every last drop. He then got up and lit a candle that he placed near the bed on a stand. He also came up with a bottle of massage oil and motioned for me to roll over. He proceded to give me a sensual but aggressive massage working this warm massage oil that smelled like sandalwood and jasmine into my body. He caressed, kissed and kneaded me from head to toe. I felt like a king. I have never quite had a massage like it. Part of me thinks that he may have enjoyed it as much as I did.

After that we cuddled for a while and talked. He is happy, he tells me. He is very happy, he says again. Still thinking that all of this could very well be a dream, I worked my way down to his lean torso. By the time I got there, his 7" cut cock was standing at attention. It is average in thickness but gets as hard as stone. The head is a large mushroom considerably thicker than the shaft under it. It is arrow straight and without any blemishes. There doesn't even seem to be a circumcision mark. As I took him into my mouth, I heard him gasp out. I continued to engulf his cock and moved a hand to his stomach to rub him while I sucked him. He was eager and after a few minutes of attention he was thrusting at the back of my throat. His eagerness told me he was excited. I grabbed both of his ankles in my hands and lifted his legs up in the air to expose his ass and began working at it. He was louder now. Not just moaning but vocal. "Fuck me!", he pleaded. "Fuck me now1", he moaned. So, I fucked him. I fucked him slow and deep. Making sure to pull almost out and them to plunge slowly back in as deep as possible. It took a few minutes of this before he shot his load all over both of us and I followed by dumping into him. We repeated this several times through the night.

It was a very nice Valentine's Day!

Sunday, February 03, 2008

It's Official!

It is semi-official. Ok, it's official! cherryboi and I are dating. I am almost embarrassed to admit this. I have mixed feelings about it. He is 25 and finding himself and I am 39, so it is up in the air about whether this will really become anything. I remind myself that this may be more about first-sex with him and a young tight boi that I am breeding for me, but I am a guy so I am enjoying the ride. And FUCK, it's one incredible ego boost!

I have been dicking cherryboi on a more and more frequent basis since last Fall, when we first hooked up. I haven’t written about him very much. He spent the night for the first time the weekend after my last post. This was more by accident on my part. I know from him that he stayed by intention. He is 25 and HOT and I have discovered quite intelligent. He is a Congressional Staffer by day and law student by night. He has worked for a Congressman for more than a year. He has a wide-eyed youthful optimism that I lost many years ago. He is one incredibly fucking hot piece of ass. I am hard just thinking about it. Shit, I feel 10 years younger lately! I can hear all of you laughing at me now. I know the upside and downside to this situation. This started out as a hot piece of ass for me and clearly he was bound to have confused feelings considering I was his first. What can I say....... one day at a time.

The other evening cherryboi was waiting for me when I got off the Metro. He had no idea when I would get to the station, so I was surprised to see him. I have no idea how long he had been waiting and I have no idea how long he was planning to wait. I had averted a previous invitation to grab dinner or a drink some time. He was there on the platform with his tussled-haired good looks and a big smile on his face when I saw him. This time he was hard to resist. He had clearly figured it that way. I didn't resist. He was right. I had no plans. I did have to eat something. The worst thing that could happen, I thought, was that I would eat and get laid too.

We chatted. We drank beer. We shared a pizza. We sparred about whether there was an us or whether it was just great sex. Then I tried to be adult and he tried to be an adult. I don't know whether we will have an enduring relationship or not, but I guess the most compelling thing he said was that he had the right to make his own mistakes. How many times have we all said that at different times when we were younger. Finally, we both drank too much beer.

The night couldn't have ended better. Me on my bed with the room spinning around and my new boyfriend giving me an incredibly good BJ! Life is good in the strangest ways and at the most unexpected times.

Saturday, January 05, 2008


I have dicked the boy I cherry popped, who I will call “cherryboi”, several times over the last few weeks. A few days after I popped his cherry, I got this sweet fucking e-mail literally thanking me for fucking him. He wrote, "You are the first guy that I have been brave enough to go all the way with. I have met 2 different guys in the past. One guy was in college and we messed around some and played with each other. We finished up by jerking off. The second guy was a guy I met about a year ago here in DC. He was so aggressive when we met that I got scared and bolted." So, cherryboi made it official. I was his first. Gotta say that I liked knowing that! Then in the hottest part of his e-mail, he wrote, "I was so scared when I got to your place that I almost bolted again. I wanted to be there, but I was freaked. I was able to get a hold on myself a little while we watched the game. The only thing that kept me there was that you took the lead and didn't give me any chance to change my mind. After we kissed I knew I had to have more! Thank you for making it so GREAT! The feeling of you cumming inside me was awesome. I fingered myself and tasted your load all night after I left. I will do almost anything if we can do it again sometime."

I am a total sucker for that kind of plea. After a few more e-mails and a chance meeting on H Street, not far from my place, we connected again. cherryboi is a delicious boi. He is every bite 6'1" tall. He says he is 25, but looks like a young college kid. He is athletic and lean and nearly totally smooth. He weighs between 175 and 185lbs. He has this sandy lifeguard-type blond hair that seems to be natural. It is a mixture of light and dark blond. His pubes and the other limited hair on his body are similar shades. He has a fresh looking boy next-door face with blue eyes, very long eyelashes and full lips. He is fucking tasty looking. I used him pretty hard, the first time we hooked up. Once I got the green light, I had my way with him including dumping a load in his tight ass. I'll be honest; there was a tinge of guilt on my part. So, I ignored the e-mails from him until I bumped into him on the sidewalk on H Street one evening after work. I was walking back toward my house and met him on the sidewalk. I would have passed him with a hello, but he wanted to chat. We chatted and he was low-key and friendly. He gave every indication that he was very pleased to see me. He asked me some random questions and as I was pulling away and saying my goodbye, he blurted out, "I'd like to come by again some time. I know I am not very experienced, but I am eager to learn." All I could do was smile and take his cell number.

About a week later, cherryboi was at my place bare-assed and between my legs with my hand firmly on the back of his head very assertively telling him how to suck my cock. I will admit that he was doing everything he could to try to do as I instructed. In the middle of his lesson, he gagged out that my cock was the first cock he had really ever sucked. And then for added effect, told me how thick I was. HOT!!! But like a good boi, he gave 110% to the effort and this time the head was better. The whole thing was a massive boost to my ego.

Then I took cherryboi upstairs, laid him out across my bed, crawled up and draped his legs over my shoulders, gently penetrated him and fucked him. He was still very tight, but this time I was a little gentler. He gasped and groaned as I worked my cock into him. I could feel the tightness of his hole clinging to my raw cock. Once I was inside him, I kept going gently building up a rhythm and listening to the change in his breathing and his moaning. As I started fucking him harder, he started to respond and I could feel his arms around me and his hands clinging to my ass. After about 15 minutes of me pounding him pretty deep and mixing it up with some full pullouts and short thrusts, I exploded into him and we immediately started to kiss passionately. I finally rolled over and lay down next to him admiring my good fortune and he moved in so that we could cuddle a little.

After a few minutes, I decided that I wanted nothing more than to fuck his well-jizzed hole again. I gave him a kiss and instructed him to go down and clean me up. I got up on my elbows, so that I could watch this hottie lick our juices of my cock. As I was sure would happen, he soon had a mouth full of hard cock. I asked him if he wanted a second load and without waiting for a response, I grabbed him and flipped him over so that I could get at him from behind.

This time his well-fucked hole was looser and my cock slipped right back in. He was still tight and clung to me, but he was filled with my load and the natural lube was incredible. The great thing to me about raw sex is the feeling of fucking a hole filled my your own cum. There is nothing like it. It is the ultimate form of topping. You totally possess the man your fuck this way. I owned cherryboi and he verified this by quickly shooting his load and using his moans of pleasure to coax my second load deep into him. I really dicked him this time.

We cuddled some more and chatted. It was very relaxed and I could tell that cherryboi was relaxed and comfortable in the aftermath of our sex.

He has been back several times since. Who wouldn't fuck this boi!