Just recently I had an experience I had to share. I wrote some time ago about my first anal at the hands of a rapist which however how frightening, actually turned out fantastic. I met up with him later and unfortunately the second time was nowhere near the first (To be fair, it had an extremely hard act to follow. My expectations were unreasonable I know - any I digress...) but I'll tell that story another day. This happened just a couple of months ago and I am still shaking just thinking about it!
A few months ago, some of my coworkers and I were planning a trip to Las Vegas and met over my apartment to finalize the details. It was four of us, all married except myself, called it "the boys weekend." Now I never thought of any of these guys sexually and I was sure they all were straight. I live a straight lifestyle and no one knows my secret luster for men (well, transsexuals actually) at least I thought. Though I'm still not 100% sure - let me finish the story. While one of my buddies, a coworker -let's call him Bobby - was in my bathroom I caught a glimpse of him out the corner of my eye. He was looking at one of the magazines I left in the bathroom. Now all of the mags are straight porn (5 in all) but one is all hot black trannies getting banged. I wasn't sure it was the one until I checked later after they left. However, when I noticed him, he was definitely aroused and was quite uncomfortable when he exited the bathroom and joined us. Bobby is a quiet nerdy guy, small in stature and actually very good looking. Now Bobby, would definitely be someone I would think was gay if he wasn’t married (for what that’s worth anyway). He has an effeminate demeanor and long brown hair and pretty blue eyes with soft facial features. I would have never embarrassed him by exposing him at the time, but when I realized it was the tranny mag that got him hard - I couldn't stop thinking about him.
Every time I jerked off the rest of the week, I thought about him! I imagine him sucking my dick real gently (like I love it!) and me cumming hard in his mouth, I even imagined me fucking him. His long hair covering his face as I'm holding both of his ankles driving my penis into his ass. The fantasies were so vivid, every time I would see him (we work at the same firm) I would get hard. He never seemed to notice or so I believe but the subsequent events are a little unclear.
Cutting to the chase, we all get the tickets, we're leaving on a Thursday morning and we're meeting at Bobby's house. All of us are there laughing and conversing just waiting for Bobby's brother to come give us a lift to the airport. Everyone is in the living room and I wandered out to the garage where all the luggage is. Bobby has a beautiful spacious home and a bar - like setup in the garage area. I walked behind the bar and there was like a powder room but with a waist high bench next to it and inside of it near the toilet. I started to use the bathroom when Bobby came quickly in and shut the door!
I jumped so fast I pissed all over the wall behind the toilet! I said "shit man you scared the life out of me!!” All he did was put his index finger of his right hand too his lips and made a ‘shhh’ noise and with his left hand, he grabbed my penis! His hand was electric and I instantly became fully erect. He whispered something to me (I couldn’t make it out) as he masterfully manipulated my dick while I was literally frozen.
As he did this, he pointed my still peeing pecker towards the toilet. At the same time, he slid in back of me. There is really only enough space for one person in that powder room at a time so he had to press his body hard against my ass to get the door closed behind him. When he did this, I leaned forward and put my hand on the shelf in front of me while he began to fondle me a little faster. I can't adequately explain all the sensations going on at one time: 1) his hand is stroking my dick and it feels amazing 2) it's the guy I've been jerking off to for the last two weeks 3) what and how the fuck did we get here??? 4) scared about being discovered but don't want to dare stop.
As he's stroking me, he starts sliding his free hand under my t-shirt and starts massaging my nipples (that are extremely sensitive). I feel his breath on my neck and he's grinding his groin hard against my butt. Then I just erupted. (I came hard too). Thank goodness for the bench or I would have fell to the floor. I remember gasping but it happened so fast.
I'm feeling pretty lightheaded and he asks me if I'm ok. I don't remember replying but he let my dick go and put both hands up my shirt and is rubbing all over me. My nipples, stomach, shoulders, back - at the same time he's grinding even harder into my butt. I put both hands on the wall and push back on him. He's making sexy little muffled sounds. Bobby’s effeminate nature was evident as he sounded like a girl in heat. As we're going at it for about another minute or so, my jeans start sliding down and he pushes them down my thighs but pulled my underwear up almost wedgie style. Now he grinding his crotch against my briefs and I can just about feel the length of his dick poking at me. I reached back and felt his bulge. He lifted up on his tiptoes, sliding up on my palm. Then he whispered in my ear "you have a big round sexy ass"
I got a chill through my whole body! I can’t tell you what hearing that did to me. It made me feel so desired. It's weird I know but as if on autopilot, I grabbed the baby oil he had on the shelf and he undid his jeans. Just like we have done it a thousand times; he put some on his hands as I reached back and massage oil onto his dick, he massaged oil onto my butthole. Now I really couldn’t tell the actual size of his penis but it felt long and very skinny. I can’t be sure because I never seen it afterwards either but I confess that it really didn’t matter to me one way or the other
There was slight pause by him and I thought maybe he changed his mind. Maybe it was too risky or maybe I wasn't as sexy as he thought at first. That quickly changed as he began to enter me. Now I've only been fucked twice (by an actual live cock that is-countless times by dildo), and the first two times there was no pain. This time it hurt. I tried to relax but the cramp space didn't help and the situation with a house full of people a few rooms over didn't make things work any better. However, I wanted this just as much as I ever wanted anything I can remember. I did ask for a little more oil and he put more than enough on us. He was gentle but urgent. Again, it didn’t matter because I don’t remember being hornier at any time in my entire life. When he reentered me, he started stroking away but the additional oil made it feel better. Then it happened...
I felt that total bliss feeling I felt the very first time I was fucked. He had me slightly bent over, both hands on the sink, pants and drawers at my ankles - him fucking away. As he slid in and out of my rectum, it felt like every stroke, tingled every part of my body. Also, at the end (or the beginning) of each thrust I got a massive chill that ran from my nipples and jumped to my balls and inner thighs-just wild awesome! I was drooling again and my eyes were open but I couldn't really see anything ... I heard myself groan, then I felt a massive orgasm approaching when Bobby whimpered breathlessly in my ear "oh fuck" shuttered violently as he came in my ass. I could feel his penis twitching in my bottom and I didn't want him to pull out so I squeezed my butt muscles and he whispered a yelp and pushed into me even further. Right there I came again... much harder than the first one. My whole body became weak as about three hard waves of pleasure rocked my body. My dick was just spewing cum. I even teared up a little it was so intense. it reminded it me of two things that have been on my mind since I lost my anal cherry. One, the intensity of the orgasm I got from just being fucked that day. It was indescribable and this one was similar. Two, I corresponded with a guy from the west coast who read my first story and told me I would love a hard fucking because he believed I may be submissive in nature. I don’t know how submissive I am, but I really liked being fucked hard by Bobby. Tremendously.
Bobby pulled out and grabbed some towels from an overhead cabinet. He came a lot! It was running down my legs so I squatted right over the toilet and let most of it out. I stood and he wiped my butthole and private parts while kissing my back. He told me that he really enjoyed what we did but better get back to the others. He helped me get dressed and turned me around in the tight space, put both arms around my neck and kissed me full on the mouth like a sexy female. Bobby’s long hair flowed like a model and his eyes looked genuine and caring. His lips were soft and sucking my mouth and his breath was so fresh. I instantly got hard again (my first time kissing a guy, it was hot!)
After we reemerged no one was the wiser and the trip to Vegas was great. Bobby never as much as directed a seductive glance the entire trip or afterwards. We've been alone on several occasions since then but he hasn't mentioned anything or tried anything sexual towards me. I'm sort of glad in a way because he's married and I wouldn't want to be in a complicated situation. I do like his wife and I feel a little guilty. However, I have to admit if he wanted to repeat our session, I'd jump at the opportunity.