I have always been a very sexual person. Coming up, I had done a lot of solo sexual exploration, this led me to discovering tons of fantasies, fetishes and kinks in my head, but living at home, I never really had an outlet for them. Throughout high school I had the same girlfriend and we had a great sex life, basically humped like rabbits, but it was always pretty standard sex and at the time I was pretty ashamed of the abstract sexual thoughts I had concocted in my head and never broached the subject with her. One of the biggest ones was loving to wear women’s clothing, make up, shoes – which I later found was called Cross Dressing. For me Cross Dressing wasn’t really inherently sexual, but it was a way for me to transform from a boy to a girl, the thought of which just made me happy (more to come on this in another story).
Fast forward to college. I move into the dorms with my new roommate, who was openly gay, we’ll call him Dan. We were pretty close (just as friends) and soon made friends with several people from our floor, we’d all go out together, eat together, study together you name it, we were close.
Dan was always very open about his hookups, regaling us with stories of random guys using him and showing off his clothes with dried cum on them after a “night out”. At this point I had really started exploring my sexuality and found myself getting really turned on by the experiences Dan was having. Now I know what you’re thinking, but Dan never even flirted with me. We were really just good friends and I was learning a lot from him. Now fast forward a year or two and that’s a different story….literally ;)
I found myself spending a lot of time online researching and after going down a deep reddit hole, I was pointed to the classified ads on Craigslist. A place where anonymous men would literally ask for a blowjob and get one after a few email responses. “This is incredible” I thought… I can start finding horny guys whenever I want and the best part was I didn’t know them and they didn’t know me. Perfect. I can keep this all to myself and satisfy my urges without anyone know (which is what I wanted at the time).
——————Finally the NSFW part of the story——————————
Now this story isn’t about my first hookup with another man, or even my second or third. To be honest I’m not sure what number this guy was. I was looking at Craigslist all the time, between classes, days off, as I’m going to bed and would end up following through on that almost as much. A few months into my Freshman year and I was transformed from a straight, vanilla-sex having, monogomist to a bit of a whore and I loved it. I have always been into being a submissive and especially in M-M hookups, I basically just give myself up to whatever he wants to do.
So one night, I scrolled through a few dozen “ads”, responding to a few and finally found one guy who was discreet and straight to the point. “Come over and suck my cock” was the gist of his message along with his address. Less than 10 minutes later, I’m getting out of my car and nervously walking up to his door. He left the lobby to his apartment open and as I walked in I considered bailing, but I was already there and was determined to be a good little whore. So I walk up to his door and go right in as instructed. Honestly I don’t even remember what he looked like because I dropped straight to my knees and went to pull out his cock. I do remember he was watching the news or something on tv and smoking a cigarette. He didn’t even seem phased that I was there, it was like I was just a service person doing my job (which I guess I was).
I pull out his flaccid shaft and start licking it slowly. I love when they start soft and grow in my mouth and I was determined to give him the best head of his life so I went all out. I started to deep throat him and lick his sweaty balls while he sat there smoking his cigarette. He wasn’t the biggest I’ve ever had, but a good enough size where he could start filling up my throat a little bit.
Eventually he pulled me up onto the couch and told me to take off my pants and that he would be right back. I figured he was going to fuck my face a little bit and wanted to play with my ass or something. So I’m laying on my stomach along the couch and he came back behind me. He climbs on top of me, his smokey breath in my ear and says “are you ready for this, slut?” .. Before I could respond I feel a drop of cold lube on my tight hole and his wet cock coming in right behind.
— Now before I go on– sex was not part of this arrangement, let alone unprotected sex. It was supposed to be a quick blow-n-go and that was it. I was not an anal virgin, but would at least confirm they were clean before letting it go further and would always use protection. Everything in my head was saying to tell him no and to not let him get away with this. But I didn’t. *I want to clearly say that I never felt like I was in danger, and though this was a bit of a stupid decision, I do not feel assaulted and am completely okay that this happened.*
As I lay there face in the arm rest of the couch and pants around my ankles, he pounded every inch of his cock deep inside me. He wasn’t very big and it didn’t hurt much. He didn’t have much of a rhythm and kinda just jack hammered me. At first I was uncomfortable with the situation, but as he fucked me and continued to degraded me, I started to like it. I loved it in fact. Even though I didn’t know this man at all, I was his to use in that moment.
I could tell he was getting close, “you’re going to take this cum, aren’t you?” he demanded and as I had started to tell him to pull out, I actually said “yes please, cum inside me”. At this point I had total slut brain and cream pies are a huge fetish of mine. He held me down harder and unloaded deep inside me. I didn’t even cum myself, but felt as excited as if I had. The whole experience was only about 30 minutes, but it felt like hours and I was out the door about 1 minute after. Excitement, shame and embarrassment bounced around in my head as I drove myself home, his hot cum leaking out of my insides and into my shorts. I got back to my dorm and Dan (remember my roommate?) was gone, I sat at my desk chair in what was now a puddle of a strangers cum, smelling like cigarettes and semen. I slid off my pants, starting to get a little sore, and dipped my finger in his seed and brought it to my tongue. This drove me nuts, what was supposed to be a quick in and out visit, turned into a longer and far more degrading experience than what I intended. I felt like such a slut and I replayed the night in my head over and over again as I finally gave my cock some attention. I barely lasted 30 seconds, before I emptied myself into my already cum soaked underwear, mixing our loads together. I took a quick shower to rinse the smell of smoke off, crawled into bed and went right to sleep.
This was about 8 years ago and I still think about this all the time. I am so turned on by this and have been edging as I write this out. Let me know if you enjoyed it, have plenty of other stories to share with Dan and many others.
Source: reddit.com/r/gonewildstories/comments/m513xe/journal_1_mm_the_time_i_18m_got_more_than_i
Great story man
Thanks for sharing it