My Unusual Situation

So, many of you have got to know Annie and myself (Cillian) during our time here on xHamster. We use the site primarily to compile a database of the images and videos that turn us on. I think we are both very happy with our favorites galleries. We also have a few galleries of our own primarily with images I have taken of Annie over the years. Reading comments from guys talking about what they would like to do Annie gave me a real buzz, not to mention the buzz it gave Annie…who then gave herself a buzz with a toy or two 😉 Annie has even taken to reading conversations she has had with guys to me while I fuck her…
Anyway, that's not the point of this blog entry. This entry is simply to document what happened to me earlier this week in London.
Before I get into the details of what happened in London I think I need to explain the relationship I have with Annie first. I know some guys out there are a little confused by what we want on xHamster. The short answer is that we are in a loving relationship and trust each other to not do anything to harm the other. We are both quite sensitive to the thought that people in our friend group/acquaintances and families might ever gain access to this part of our lives. This is part of our relationship that we keep private (in the sense that people who know us in real life don't know us here in xHamster).
The longer answer is that we like to tease each other, and I get turned on thinking about Annie being with another man, or woman. This fantasy turns her on as well, and as anyone who has engaged in a chat with Annie can testify, she is a very open minded sexy young woman. I am very glad she is so open minded. Without that, our relationship would not have lasted this long. You see, I am a straight man, who has a rather specific fantasy… I would love to be a woman for a night to experience sex with men.
I am not attracted to men, and I think it would be a stretch to call myself bi… I guess I am bi/curious? So in an earlier blog entry I wrote about my first time giving a guy a blowjob. That was about 2 years ago now in a gay cinema in Amsterdam. I was very lucky it was a fantastic experience. The guy I met was in great shape, had a lovely clean cock and was very helpful 😉
But it has taken me 2 years to work up the courage to try something new. So I travel a little bit for work. On one of those trips I downloaded Grindr and spent an evening chatting with random guys near my hotel in Berlin. I came close to inviting a certain guy to my hotel, but in the end I chickened out and had a wank instead. The feeling of getting that close to getting a guy in my hotel room stuck with me, and stills gets me aroused every now and then.
So earlier this week I was in London and I decided to download Grindr again one bored night in my hotel room. I was only there for 2 nights so I figured, why not!? On the first night I had a couple of nice conversations with a couple of young guys. The guy who was most interested in meeting me wanted me to come to his place… Again I chickened out, told him I was already in bed, sent him a pic of me naked under the sheets and told him he was welcome to join me. Unfortunately he wasn't willing to leave his place. So, yet again I was left having a wank. I watched a compilation video of hung guys blowing their loads all over young girls. One of the girls looked so much like Annie I had to do a second take! I blew my load almost instantly… then I looked at the images of Annie and read a couple of the comments from guys (and girls) wanting to pound her perfect ass and before I knew it I was jerking off again.
On my last night I didn't get back to my hotel until after 02.00. I was a little tipsy after drinks with a colleague after the conference so when I went on Grindr to check for messages I was more adventurous than ever before. I started chatting with a number of different guys and wasn't at all coy about what I wanted. I told them all flat out, “I want to suck a cock. I have no interest in being sucked off. I want your cock.” I did leave the possibility of more on the table, even though I rarely play with ass plugs or dildos. I do have a fantasy about standing in a shower while a hung guy walks up behind me. He stands close enough to me that I can feels his semi-hard cock between my ass cheeks… I stand, frozen to the spot while he pushes closer to me and his cock hardens against my skin. I have to say this fantasy comes directly from Annie. She told me a story about being in a nightclub dancing with a group of her friends. This group of guys merged with hers and she ended up dancing with a pretty tall guy. She was wearing her tight red dress which perfectly shows off her ass. It didn't take long for the guy to press up against her as she swiveled her hips. Hearing her describe the shock/pleasure at realizing he had a massive throbbing hard-on made a lasting impression on me. How amazing must it be to know that you can have that affect on a guy? To know that you have that kind of control over a guys body…
By 04.00 in the morning I had engaged in a number of erotic (blunt) conversations with guys quite near my hotel. I was shocked at just how many guys were online at that hour, and how many of them were interested in me. It gave me a thrill again. I started chatting with a 19 year old guy, whose handle was “Bored tonight”. We chatted for a while and I explained again that I was looking for a guy to blow. After about 15 minutes of messages back and forth my phone buzzed to alert me to a new message: Bored Tonight: “I'm coming over”. I asked him if he was serious? At this stage I had kind of given up on the idea of anything happening, it was almost 04.30. Then I got a message asking me to come to the lobby to bring him up, he was scared. I told him my heart was pounding as well, don't worry about the night watch. Just walk to the elevator like to own the place. 5 minutes later the was a knock on my door. I nearly wet myself. Was I really doing this? Thankfully I didn't think too much about anything, told myself to commit to this and go with it.
I opened the door and let Bored Tonight into my room. He was slim, tall and handsome. Not pretty, at least he wasn't feminine, handsome, in a cute kind of way. After a little nervous random chat about nothing and television, BT heading into the toilet and I got into bed. He returned after a few moments, removed his trousers and climbed in next to me. We lay next to each other for a while, chatting randomly again. The conversation died under the weight of expectation and we both turned onto our sides to face each other. I slowly moved my leg so it entwined in his. We moved a little closer and I moved my knee up between his legs until I touched his crotch. He leaned forward and I kissed him. I was the first time in my life that I had kissed a guy. I committed to everything. Before too long my hands were wandering all over his body. I undid the buttons of his check shirt and made him slip it off. I ran my hands all over his slim defined body. Eventually my hand went after what had been my desire all along. I rubbed his stiffening cock through his white boxer briefs. I quickly positioned myself between his legs and ripped his briefs off revealing his cock. And what a cock it was. Despite his slim frame his cock was fantastic. It must have been close to 8 inches long, but it was thick. I could barely touch my finger to my thumb around it. It was much thicker than mine. I wasted no time going down on him. Sucking for all I was worth. I tried repeatedly to take him all the way down but I didn't get close. But I kept trying, each time coating his glistening cock in more of my spit. He had large balls for a guy so young as well, and they were nicely shaven. After about 10 minutes of persistent sucking on the head of his throbbing cock (and a decent speed wanking) I heard his breathing quicken and I noticed his legs start to tense. He grabbed onto the bed sheets and I sucked for all I could muster. I felt the first stream of cum hit the back of my throat so I buried his cock as deep as I could manage into my throat. I took every drop of his cum and swallowed every bit. I then spent a few more minutes licking his cock top to bottom again. As it softened slightly I rubbed it all over my face and slapped it against my cheek…
We fell asl**p soon afterwards. When I woke a mere 2 hours later Bored Tonight was lying in his briefs and shirt again, but still on my bed. One of my favorite videos on xHamster was of a girl waking up her boyfriend with a blowjob in the morning. I spent a bit of time thinking about that. I also thought about how hot it would be to see Annie work with a tool this big. Thinking about what she would do to a body like this with her body just tipped me over the edge and although I was now completely sober, and could perhaps have been feeling a little sheepish after my escapades from the night before, but the thought of Annie fucking a cock like this was enough to spur me on.
I slid across the bed, and gently started rubbing his beautiful cock through his briefs. I gently pulled the briefs down his legs and threw them to the floor. He stirred almost unnoticeably but didn't open his eyes. I took as much of his semi-flaccid cock in my mouth as I could. (He was a shower and a grower…just a little jealous!). Feeling him get hard in my mouth as I gently sucked and rolled my tongue around his member was amazing. It didn't take him long to get fully hard again. Once he was there I imagined I was Annie, slapping his hard cock against my face and rubbing my spit all over my face. After a few minutes of frantic sucking he tensed and grabbed the sheets again. This time I deliberately wanked him off onto my face. The first stream of cum hit me just before my left eye and immediately ran down my face , dripping off my cheek onto his leg. The second and third streams followed quickly and hit my nose and lips. I greedily licked and sucked the cum off his legs and from my fingers. Then I used it to lube his cock with I milked the last drops of cum from his teenage balls…
BT got dressed (without any clean up) and left within minutes of cumming. I was left lying on my bed with cum on my face, in my mouth and on my bed… I slowly climbed into the shower and immediately regretting not asking him to join me. I could have fulfilled the fantasy of having a naked guy pressed up against me from behind… Perhaps next time? 😛
What does this say about me? Does this mean I am a cuckold? At the very least it means I have fantasies which lean that way. I guess it also means I am willing to act on those fantasies. Still immensely turned on by both the thought of sucking, and possibly being fucked like a slut some day. I'm going to have to go have a wank dreaming about Annie being fucked my a hung guy… For my next time I'd like to meet a guy with more experience who is willing and able to dominate me…(or me thinking of Annie 😉 )

Like I said, I love Annie and I love her open mind 😉