Being in my late teens and being a virgin was troubling. I liked girls and even had several girl friends over the years, but never had sex to this point. I was feeling a little desperate, desperate to have sex, so I tried looking online, hoping a casual sexual encounter might help me feel more confident in having sex, and going into this, I never expected it to be a gay sexual encounter.
For as long as I can remember, probably ever since I was very young, I had thoughts about having sex, and later I even found myself considering, let’s say having a gay sexual encounter. Yea, of course I thought about girls, and I did have several girlfriends over the years. However, being I was so shy, I had never had sex, and even though I had plenty of opportunities, it just hadn’t happened.
At the time of this story, I was in my, well late teens, but I remember from very early on, like most red blooded young guys, I found myself looking at porn, and thinking about what it would be like to actually have sex with any of the very attractive girls. I had become obsessed with watching porn and over time, I even found myself looking at the guys in these porn videos, thinking they too were very attractive. I know it was weird, and I didn’t think I was gay, but seeing their hard cocks in the sex scenes was more than a little erotic.
It was definitely a turn on to see good looking girls and guys having sex, and at some point, being I was a little sexually deprived, I ended up checking out gay porn, wanting to see what it would be like as I watched guys having sex.
Watching it was very graphic, and I found myself fantasizing as I thought about what it would be like to have sex with another guy. As I watched two very attractive guys having sex, my thoughts would wander, and I’d eventually start to masturbate, thinking about being in a gay sexual relationship. It was definitely erotic to think about, but afterward, after cumming, I’d catch myself, realizing it was wrong.
It was only for a fleeting moment because I knew it was wrong to consider. Yea, I of course continued to think about girls, and at the time, I was in a relationship with an attractive girl at the time, but being I had still never actually had sex, the thought of having a gay sexual encounter was for some reason always in the back of my mind.
I was so shy, but I wanted to have sex, however being I was struggling to make a move, I found myself searching for a way. I was really becoming a little desperate, and wanting to take a chance, I started looking online for a possible casual hook ups, thinking this might help break me out of my shell.
At first, I was looking to find a girl that might want to meet up, and there were plenty of dating sites, porn sites, and casual encounter site to choose from. Taking a chance, I signed up for several of these sites and created profiles so I could start looking at postings and contact other people. However, I found that I was too nervous to contact anyone, but as I continued to look through profiles, I eventually started to contact several girls I found attractive, but still was nervous to meet up.
I was close several times, and continued to get messages from so many girls, but I also felt most were scams. Nervous, I still continued to look at possible people to contact, trying to find those genuine posting. There were so many girls that said they lived close by, but most I thought were either way too old, too fat, married, or looking for a donation, which signaled they were probably prostitutes.
It really made me nervous to contact any of them, and when I started to notice I was getting messages from guys too, asking to hook up. It was intriguing as to why, and it did make me smile, but I still thought it was wrong, or that it was possibly a scam, so reluctantly I simply deleted them.
Again, I continued to get messages from girls, and hoping they were real, I messaged them back. I wanted to find someone to meet up with, and made arrangements several times, but hadn’t gone through with it, not yet.
I continued to check my messages pretty much everyday, and hoping there would be that one that stood out, and strangely there was this one guy, yea a guy, that continued to message me. He wasn’t asking to hook up, he was simply looking to chat, looking for friends. He seemed genuine and it seemed he too was looking for girls to meet, so I ended up send him a message back.
Looking through his profile, he said he was in his thirties, but I suspect he was maybe in his forties, and from his pictures, he looked to be in fairly good shape. Continuing to look at his profile, it said his name was Jim, which I felt was an alias, and that he was divorced. He listed himself at 5 feet 10 inches tall, which was a little short than me, and that he weighed 180 lbs, but looked to be heavier than that.
Scanning through his friends list, he had many friends tagged on the site that were girls and guys, some of the girls he had tagged we even had in common. Feeling it was okay, I contacted him. It was a simple message and over the next few days, we messaged each other a lot.
It was fine I thought, but when he started sharing pictures of himself, even though they were simple, I was leery to send picture of myself back. Yea, I of course looked at them, and found myself becoming more curious, thinking, well you know, and when he asked me to send some pictures too, I was still reluctant. It did however, make me smile, all the attention he was giving me, and I did end up sending a couple pictures.
It made me a little nervous, but when he messaged me back that I was handsome, and remarked that I looked to be in good shape, and that I was taller than him, I didn’t know what to say.
Again, it did make me smile, and when I didn’t responding right away, Jim responded back saying, “I didn’t mean to embarrass you,” and continued by saying, I’m sorry if I did.”
We had always just made idle chit chat, and feeling it was an innocent comment, I naively messaged him back, “Don’t worry,” and then naively said, “You’re handsome too.”
Realizing I probably shouldn’t have said that, I waited nervously to see his response, all the time hoping he wouldn’t. However, he did, and after simply saying, “Thanks,” I got another message.
Opening it, i was shocked, it was a selfie of himself, nude in the bathroom mirror.
“Oh my god,” I thought, “why would he do that?“
It was troubling at first, but again being curious, I looked. The picture conveniently blocked his face with his phone when he snapped the picture, but it did show his muscular chest and arms, his poochy stomach, think thighs, and of course his cock.
He was clean shaven, had dark hair, dark skin, and naked, he looked in really good shape. Hid chest and stomach was kind of hairy, probably because he was much older, but again I was immediately drawn to his crotch and his muscular looking thighs. I could see he was circumcised, and even though he wasn’t at all hard, his cock looked to be kind of big as it stuck out of his dark tangled pubic hair.
Continuing to, I guess fantasize as I looked at his cock, I thought, “Maybe it looks big because of the angle of the selfie or maybe it’s because he wasn’t real tall,” in either case, I couldn’t help but smile.
Red It was a turn on to say the least, and naïvely thinking it was okay, I decided that I’d send him a nude selfie too. Taking a few pictures and deciding on one, I sent it. At first, I smiled, but soon after I pressed send, I thought to myself, “Why did I do that?”
Hastily, I tried to delete the message, but it was too late, he had already opened it.
Nervous, knowing he was looking at it, I thought to myself, “What would he think?”
Jim didn’t respond right away, which made me even more anxious, thinking, “He didn’t like what he saw.”
It seemed like I waited forever for a response, but eventually he did message me saying, “You’re in good shape,” and before I could even think about responding he blurted out, “What are you looking for?”
I was nervous what to say, and even though I knew I was looking to hopefully hook up for sex, but not at all thinking about being with another guy, I didn’t respond. Unsure what to do, I instead waited nervously for him to message me again, and when he eventually did, it simply suggested, “Do you want to meet up?”
It shocked me a little, I wasn’t expecting it at all, and when he messaged me again saying, “I understand if you don’t want to,” I again got another message saying, “I think we’re looking for the same thing here.”
Again, I didn’t know what to say, and after a little bit, he replied, “It’s okay if you don’t want to.”
Looking at his nude selfie, continuing to be a little curious, I wondered what it might be like, but then quickly decided, “No, I can’t go through with it.“
However, he again messaged me saying, “No strings,” I again thought about it and feeling it was innocent, I decided it would be okay.
I didn’t want to think that he was wanting to have sex with me, but yea, I thought about just that, and taking a chance I messaged him back simply telling him, “Sure.”
I’m sure it probably excited him, because he didn’t respond right away. I was young, tall, well built, not at all fat, and I’m sure he was thinking that I had never done it before, or at least never with another guy.
Eventually, he sent me an enthusiastic message simply saying, “Great!” and then suggested that we meet at this particular Mexican restaurant that I figured was most likely close to where he must live.
I really couldn’t believe that I had agreed to meet him, and like before I was nervous to actually go through with it, but curious too. Agreeing to meet up later the next day, I immediately had conflicting thoughts that he might proposition me, thinking, “What should I do.”
It did make me smile to think he might actually be interested, and wanting to give a good first impression, I cleaned up best I could, and I know it’s weird but I made sure to, clean up and, clean out my ass best I could.
Obviously, I was having conflicting thoughts about what to expect, but I was excited to meet him. As that afternoon came around, I tried to dress casual but nice, and when it was time, I took a deep breath and headed off. I wanted to get there early, but ended up getting there a little late, and as I scanned the restaurant, “There he was,” or at least I thought it was him.
Going over to the booth where he was sitting, I smiled and asked, “Jim?”
Nodding, he reached out his hand and when he said, “Have a seat,” we shook hands.
It made me smile, and as I sat across from him, we looked at each other not saying anything for a moment. Eventually, Jim leaned forward and said, “It’s nice to finally meet you.”
I was so nervous, I didn’t know what to say, and sitting there, stupidly grinning, I thought, “What am I doing?”
I’m sure he could tell I was nervous, and when our waitress came over to our table and she asked if she could get us anything to drink, I panicked. However, as Jim ordered a rum and Coke, he looked at me and smiling he said, “Make it two.”
The waitress looked at me questioningly, and then smiling she simply said, “I’ll be right back.”
After she left, Jim said, “I hope it’s okay that I ordered you one.”
I knew he had to know I wasn’t old enough to drink and after a smile, I took a big drink of water. I continued to be super nervous, and for some weird reason, I wanted it to go well, and as we got to know each other, I sensed he was interested in, … being more than just friends.
As we continued to talk, getting to know each other, he was very personable, and I don’t know if it was the liquor or not, and I would never tell him, because I still felt it was wrong, but I was starting to feel the same way.
He was an attractive guy, obviously needing no help getting girls, and being he was so much older, and he was nicely dressed, I felt he must be well off too.
Anyways, as we finished our dinners and another drink, I could see it was getting late, which made me look out one of the windows. Seeing me looking out the window, I think he thought I wanted to leave, and not wanting to lose the opportunity, he suggested, “Why don’t we take this to my house.”
Looking over at him, I’m sure he could see my apprehension. We had just met and I wasn’t thinking I wanted to go with him, but as he reached across the table and I looked up at him he asked, “What do you think?”
Seeing him smiling, I felt he was hard pressed, obviously wanting to get me alone, which made me hesitate. I didn’t want to think he was gay, but seeing him waiting for an answer, I nodded, and naïvely said, “Okay.”
I think it kind of surprised him, and it did make him smile, and then pulling back his hand, trying to not appear overly anxious, he flagged down our waitress, quickly paid the bill, and then asked, “Are you ready?”
Looking over at him and seeing his excitement, I again became apprehensive, but ended up simply replying, “Sure.”
Smiling, we both got up to leave, and as we left the restaurant, continuing out to the parking lot, he asked, “Do you want to follow me?”
I was nervous, but when he said, “I live close,” I couldn’t help but smile, and agree saying, “Okay.”
He eventually stopped by this row of cars, and when he said, “This is me,” I looked to see what he was driving. Like I thought, “He was well off,” driving what looked like an expensive Audi.
I’m sure he could sense my awe, which I’m sure he was looking for, being I was so much younger and obviously impressionable, and when he again said, “Ready?”
I smiled and after a nod, I replied, “Okay.”
He smiled and as he got in his car, I hurried over to mine, and quickly backing out, I followed him out of the parking lot. I tried to follow him kind of close, but not too close, and he actually didn’t live very far away. Pulling into a pretty nice neighborhood, I was excited to see where he lived, and as I continued to follow him, we ended up pulling into the driveway of a nice two story home.
I was becoming overly nervous to be there, but tried to convince myself that it was okay, because he was friendly, and I never felt pressured. He had parked in the garage, and as I got out of my car, he motioned for me to follow him saying, “Come on.”
Smiling, I followed him in through the garage and after going through the kitchen, we went Into the living room. Sitting down, we ended up talking again for awhile, and when there was lull, he offered me something to drink.
I think he needed time, time to create some kind of a plan to gain my confidence so he could get me to have sex with him, and one of those schemes I think was to get me drunk. However, when I politely said, “No,” he stood up and asked, “Are you sure,” as he headed toward the kitchen.
I was already feeling no pain, and when I again said, “I’m okay,” he continued into the kitchen.
He came back with what looked like another rum and Coke, and sitting down, he moved a little closer to where I saw sitting. It made me a little uncomfortable and when I looked over at him, he took a drink and then sitting it down on the coffee table, he shifted a little. Facing me, he smiled and then taking my hand he said, “If you don’t want to do this, it’s okay.”
Looking down for a second at him holding my hand, I hastily looked up, because I knew what he was leading to and seeing him smiling, I unknowingly smiled too. I was so nervous, and maybe I should have expected it, or maybe I was wanting it to happen, but when I didn’t say anything, he gave my hand a squeeze and asked, “How ‘bout we go to my bedroom?”
I was hesitant; I knew where it was going to take me, and I really should have known this is what he was wanting, and deep down, maybe I was thinking it too. It still made me nervous and even though I had seen videos of guys having sex, I really had no idea what I would be expected to do, I again started having second thoughts about going through with it. I think in a way, he knew I was unsure, because as he stood up, and he pulled me to stand too, I pulled back.
However, as we looked at each other, I scooted to the edge of the sofa and smiling, I stood up. As we stood there, looking at each other for a second, he asked, “Have you,” and then after a pause he took my hand and continued by asking, “you know, done this before.”
Not knowing what to say, not wanting to appear that I had never had sex, I looked at him and when I still didn’t say anything he said, “Just relax,” and then told me, “Let me just,” but before he finished, he said, “Now you’re gonna make me nervous.”
I knew what he was wanting to say, it was what I needed, and as I looked down at him holding my hand, I smiled as he turned and led us toward his bedroom. Going through the door, he turned and as we looked at each other, he immediately started trying to take off my shirt.
It was relatively dark in his bedroom except for the light coming in from the hall, and when I obligingly lifted my arms, he quickly pulled it up over my head, and tossing it aside, he started feeling on my chest.
Looking down at his hands on my chest made me nervous, and I’m sure he could tell, and wanting to again ease my mind, he took off his shirt too. Looking at each other, he reached down and taking my hands, he placed both of them on his chest. Feeling on his muscular hairy chest made me look up, and seeing me looking at him, he leaned forward and tried to kiss me.
It scared me, and when I pulled away, he told me, “Don’t worry,” and then said, “Close your eyes.”
Smiling cautiously, I did what he asked and as soon as I got my eyes closed, he pressed his lips against mine. It was only a simple little kiss, but it did make me drop my hands and pull away. Looking at each other, he smiled and said, “See, that wasn’t so bad, was it?”
Again, it made me smile and when I said, I’m scared,” he again told me to close my eyes.
Licking my lips, I smiled and again closing my eyes. Trying to keep them closed tight as he pulled me closer. he again kissed me. It was longer this time, and as he held me, he tried to push his tongue into my mouth. Feeling this, made me wince and when I pulled away yet again, he continued to try to hold me and ask, “What’s wrong?”
I didn’t know what to say, I was just nervous and when he again said, Don’t worry,” I again smiled.
He too smiled, and when I looked at him he asked, “Do you wanta stop?”
It was nice to hear that he was okay with stopping, and it did put my mind at ease somewhat as we looked at each other. But, I smiled and shaking my head, trying to indicate that, “No, I didn’t want to stop,” he dropped his hands off my shoulders, sliding them down my chest and my stomach. He eventually had both his hands on the front of my pants and looking at me smiling , he fumbled to undo the button.
Nervous, I looked down watching, and when he got them undone and unzipped, he looked at me as he pulled them open. Smiling at each other, he said, “Just relax,” and as he reached in my pants, searching for my cock, he suddenly knelt down. It scared me and when he started to pull my pants down, I hastily grabbed at my underwear, holding them so they wouldn’t come down too.
Looking up at me, Jim smiled, and after I stepped out of my pants, he started fondling my cock through my boxers. I was kind of hard, but not really, and as I continued to watch, he leaned forward and mouthed my cock through my underwear.
I froze, not knowing what to do, and when he started pulling my boxers down, and my cock eventually flopped out, I became hesitant. Jim eventually got my boxers all the way down to my feet, and after looking up at me smiling, he grabbed my cock and started pulling and stroking it, giving me a handjob,.
He obviously wanted me to get hard for him, and I did, but I started to get a little concerned about being safe and as I watched, he suddenly took my cock in his mouth. It made me pull back, hesitant but I didn’t stop him and as he continued to jerk me off, sucking my cock and fondling my balls, I tried to tell myself, “It’s okay.”
Closing my eyes, I tried to just let it happen and when I casually put my hands on his shoulders, he pushed me, backing me up against the end of the bed. Sitting back smiling, Jim pushed on my legs and saying, “Scoot up.”
Smiling, I moved up on the bed and as I sat there, he moved closer and went back to sucking my cock. It really felt good, but I struggled with the thought that it was a guy sucking me. Jim gad brought his one hand up to my chest, trying to steady me, I instinctively leaned back on my elbows and thought about wanting to cum.
Jim however stopped, and when asked, “How’s that feel,” I simply smiled.
Smiling too, he immediately went back to sucking my cock, and wanting to cum, I tried to concentrate on cumming in his mouth. Jim again stopped, and looking at me he asked, “Are you going to cum?”
Smiling, I said, “Yea,” and as he went back to sucking my cock, I tried to block out that it was a guy sucking me, and simply focused on cumming before he stopped again.
I was close, I was going to cum, and when I started subtly thrust my hips, fucking his mouth, I reached down, touching his head. I’m sure he knew I was close, and when I tensed up and hyperventilated a little, he stopped sucking, but kept stroking my cock, deliberately keeping my dick in his mouth.
He was obviously preparing for those first few blasts of cum, and when I grabbed at his head, and he felt my cock start to pulsate, he again stopped, letting cum shoot in his mouth. I think it surprised him a little, because he seemed to pull my cock out just a little, keeping just the head in his mouth.
“Oh my god” it felt so good to cum, and as the pulsating became more faint, almost nonexistent, I felt him swallow. He was smiling, I think, and as he again started sucking and milking my cock, wanting the last little bit, I started to go limp. Dropping my hands to my sides, I again felt him swallow, and needing him to stop, you know because of that feeling you get, I leaned up, and smiling, I asked him to stop.
Sitting back too, continuing to stroke my now limp cock, Jim looked at me and smiling he asked, “Did that feel good?”
“Oh yea,” it felt good, but again being it was a guy, I simply smiled. I knew I was probably blushing and after patting my leg, he stood up, and looking at me he asked, “Do you wanta try?”
Looking at him, I knew what he was trying to say, but I was scared, and the thought of giving him a blowjob wasn’t sitting well. Looking up at him, hesitantly, Jim smiled and then taking my hand, he pulled me off the bed. Kneeling in front of him, I looked down and seeing him stroking his hard cock, the thought that we should be safe returned.
Seeing my reluctance, Jim now took my hand and put it around his cock. Feeling it, I looked down, and realizing just how big he was, I smiled to myself. Yea, maybe it was the liquor, or the heat of the moment, but I wanted to try sucking him, however as Jim started having me rub his cock, moving my hand up and down the length, I was actually okay with it.
Again, feeling just how big, and hard he was, I looked up, worried. Seeing him smiling, I naïvely smiled too, but when he put his one hand on my shoulder and he pulled me closer he said, “Go ahead.”
Thinking he was just kidding, I smiled to myself, but when he guided his cock toward my face, I let go, scared. Looking up at him, he moved closer and when he touched the head of his cock to my bottom lip, I looked down.
I had thought about this, but right now I was scared, and when Jim said, “Open your mouth,” I again looked up.
He again told me, “Go ahead,” as he again touched his cock against my lips. Reluctantly, I opened my mouth, and when he put it in, I closed my eyes.
Putting his hands on my head, he pulled me forward, and inadvertently forced his cock deeper into my mouth, which made me gag. Pulling away, scared, I pushed on his thighs, and let his cock drop out of my mouth. Looking down at it, Jim immediately grabbed his cock and when I nervously looked up at him, he again told me, “Open you mouth.”
He was again guide his cock back toward my mouth, and with my hands still on his thighs, bracing myself, I looked down, closed my eyes again, and half-heartedly took it in my mouth. Jim put his hands on my head again, and immediately started moving my head back and forth, guiding me to suck his cock.
He really felt big in my mouth, and when he moved closer and he started bucking his hips into me, I started to worry, “Is he gonna cum?”
I couldn’t believe it, I was sucking his cock, and as he continued to buck his hips into me, I tried to accept what was happening. However, suddenly he stopped, and backing away a little, he reached down and pulled me up. Looking up at him and seeing him smile, I swallowed hard, and after a few seconds he jokingly remarked, “Are you sure you haven’t done this before.”
Hearing this made me smile, and without saying anything, he turned me, and pushed me toward the bed. Standing there, I rested my hand on the end of the bed, and looking back apprehensively, I watched as he grabbed a tube of lube off the dresser. Moving back over to the bed, he casually tossed it next to me, and realizing what he was wanting to do now, I turned my head, facing away from him.
Looking away, I tried to prepare myself for what was coming next, and as he spread my ass, he pushed up against me, letting his cook ride up and down in my crack. Jim now told me in a stern voice, “Get on the bed.”
It again made me smile to myself, and when I didn’t move fast enough, he pushed me to get on the bed, guiding me to move up further. His demeanor had definitely changed and when he instructed me, “Stay on all fours,” I looked back to watch as he climbed on the bed behind me.
Moving up closer to me on the bed, he spread my legs, which made me again glance back. Feeling on my back and my ass, he tried to get in a comfortable position, which made me smile. Seeing me looking, he started stroking and pulling on his cock. He was definitely big, and seeing it, I turned back, and facing forward again, I smiled tentatively, thinking, “Oh my god, he’s going to fuck me.”
Telling me to put my head down, I leaned forward resting my head on my arms. I was in such a vulnerable position, I knew that, and when Jim happened to push against my ass, I took a deep breath thinking, “This it.”
However, he was just reaching for the tube of lube that was laying next to me, and smiling, I took another deep breath, relieved. Jim now straighten back up, and turning my head slightly, I looked back to see what he was doing. Hearing him flip open the tube of lube, I nervously leaned forward, resting on my elbows.
I could hear him squeezing some lube out on his hand, and when I heard him close the lid, and start to slop some lube on his cock, I again braced myself. Tossing the tube of lube on the bed, Jim simply told me, “Try to relax.”
Feeling him move up closer, I gave a little nod, and shifted a little, trying to get more comfortable.
He was now trying to spread my ass cheeks with his one hand, and when he happened to touch my butthole with one of his fingers, I pulled away thinking it was his cock. Immediately, Jim told me, “Don’t worry,” and feeling him teasing my butthole with his fingers and try to spread it, I tried to block out what was happening
Again, he told me to relax, and when he subtly pushed his finger into me, I instinctively pulled away a little. I couldn’t believe what was happening, and even though I had fingered my ass, and even used toys before, I had never had someone else doing it. Continuing to be nervous about what was happening, I tried to relax as Jim started fingering me again.
It was actually feeling good having him fingering me, but when he tried to push two fingers in my ass, hoping to loosen me up a little, I push backed, accepting it.
I’m sure it was a turn on for him to watch, and think about fucking me, as he twisted and turned him fingers in my tight little hole. Trying to relax my whole body, Jim said, “Yea, that’s it.”
Taking him fingers out of me, he moved closer, and again rubbed my ass, making sure to spread my ass cheeks. Telling me to relax as he pressed his cock into my crack, humping me, I knew it wouldn’t be long before he would try to fuck me. Knowing his cock was so much bigger than his finger, even two, I braced myself.
Jim now pushed down on my back, telling me, “Move down,” and then say, “Relax.”
He wanted me to lower my ass, so I was in a better position for him and after lowering my ass he said, “Yea, that’s it.”
Pushing the head of his cock against my butthole, and then into me, I arched my back, and tried to relax, letting him do it. At first, it was okay, but sUddenly as he continued to push into me I thought, “Oh my god.”
The pain was excruciating, and when I rose up and pulled away, his cock slipped out. Taking a deep breath, I smiled to myself thinking, “I can’t do it.”
He was obviously frustrated, and I could hear it in his voice when he asked, “What’s wrong.”
I had thought about this for awhile, and had wanted to feel it, but the pain was overwhelming. Looking back at him, I simply told him it hurts.
Hearing this, Jim rubbed my ass and told me, “You’re really gonna need to relax.”
Taking a deep breath, I said, “Okay,” and then asked, “Just go slow, okay.”
Again, he felt on my ass, and after fingering my ass again, he moved closer, pushing his dick into my crack. I wanted it to happened, and when I felt him again trying to push the head of his cock into me, I again took a deep breath and tried to relax.
“Oh my god,” it still hurt! I tried to relax and even reached back pushing on his thigh, and hoped he’d stop. He was in me, but I again rose up and remarked, “Oh my god,” and tried to pull away.
Holding me by my hips, not letting me pull away, he again in a frustrated voice said, “Relax, “ and then told me, “Let it sit there.”
Shifting a little, I again blurting out, “Oh my god.”
He knew it was hurting, and I thought, “I can’t do it,” but when Jim happened to pull out just a little, it helped.
Again, as held me by my hips he said, “Just let it sit there.”
It still hurt, I needed him to stop, but instead when he asked, “Do you want me to keep going,” I unknowingly replied in a labored voice, “Yea.”
Pulling me back, pushing his cock in me again, it again hurt and reaching back, pushing on his thigh, I rose up.
Pushing me back down, he again told me to let it sit there, and again asked, “Do you want me to keep going?”
“Oh my god,” I thought, “it hurt so bad,” but not wanting him to stop, I nodded and hyperventilating I simply said, “Go slow,”
Pausing, he asked, “Are you sure?”
I could hear it in his voice, he was enjoying me being in pain and as he continued to hold my hips, I wiped the sweat off my forehead and again said, “Just go slow.”
Pushing into me again, he started trying to fuck me, and even though he was trying to go slow, it still hurt. I know he knew it was continuing to hurt, there was noway he couldn’t, and even though I reached back pushing on his thigh, he didn’t stop.
Jim started to fuck me more deeply, more vigorously, which made me moan slightly and constantly say, “Oh my god.”
I knew he was going to cum, I could hear it in his breathing, and it was a little unsettling, listening to, and feeling his body slapping against my ass. My breathing too had become more labored, and the sound of his cock sloppily going in and out of my hole, told me, “Yea, he’s gonna cum.”
Jim did stop now and then, but it was only for a moment and I’m glad he did, but I think it was only to catch his breath, and really I think he liked watching his cock going in and out of me.
I wanted him to finish, but every time he would start to fuck me again, I desperately tried to relax, letting him do it. The pain was almost tolerable at time, and when I would ask him to slow down, he would say in and out of breath voice, “Don’t move.”
He was obviously trying to concentrate because he was close, and as he continued to fuck me, moving me back and forth, he suddenly pushed deep into saying, “I’m gonna cum.”
Continuing to hold my hips, he gave a few more short thrusts and then stopped. I could feel it, his cock was bucking faintly inside me, and knowing he was cumming, I now just wanted him to finish. However, he again started fucking me, but only briefly, and when he finally pulled out, he grabbed his cock, and I could feel him squeezing whatever cum was left out on my ass.
I smiled knowing he was done, or at least I thought he was, but when he again suddenly pushed his cock back in me, I thought, “Oh my god, what is he doing?”
It hurt, I wasn’t expecting it and when I tried to pull away, he immediately grabbed my hips, holding me close. He only pumped his cock in and out of my ass a few times. and when he again pulled out he asked, “Are you okay?”
I was nervous about what we had just done, and feeling maybe a little ashamed, I simply said “Yea.”
I’m sure he must have sense something, but shrugged it off, by saying, “That was awesome, don’t you think.”
When I again didn’t say anything, Jim started gently feeling on my ass, spreading my cheeks. When he was doing this, it made me a little self conscious that he was wanting to see his cum leaking out or my gaping little hole, so I tried to squeeze my ass cheeks together. Sensing I might be a little embarrassed, Jim eventually rolled off the bed, and headed toward the bathroom at the back.
Looking over at him, and seeing me looking, he motioned toward the bedroom door, said, “You should probably go use the bathroom,” and then suggesting, “Why don’t you use the one in the hall.”
Quickly, I slid off the bed, and as Jim ducked into the bathroom, I hurried out of the room, heading toward the bathroom in the hall. Closing the door, I locked it, and then as I sat on the toilet, I wiped my ass, wanting to see what might be on the toilet paper, and hoping I wasn’t bleeding.
Not seeing anything except what I thought was lube, I smiled, feeling a little relieved, I simply dropped the toilet paper in the toilet.
Feeling I now needed to pee, I stood up and after peeing, I felt like I needed to poo too. Sitting back down, I tried to push out whatever I could, and when a glob of what I thought was poo suddenly plopped out, I again wiped. Looking at the toilet paper again, I was confused, it wasn’t poop at all, it was, “Oh my god,” lube and as I looked closely, I thought, “It’s cum!”
Standing up, I looked in the toilet and see lube and cum, some that had sank and some that was floating, I panicked. I couldn’t believe what I had just let him do. It was my first time ever having sex, and being I had just let another guy fuck me, and cum in me, wasn’t sitting well with me right now.
I was scared and thought, “What if I get a disease?”
Sitting there for a moment, I again wiped my ass and after gathering my composure, I knew he was back in the bedroom waiting. Heading back to the bedroom, and going through the bedroom door, there he was, sitting on the bed. Standing there, I could see him smiling and when he stood up too and came over to where was he asked, “Is everything okay?”
Continuing to worry about him cumming in me, and probably feeling ashamed, I told him, “ Ivthink I need to get going.”
Giving me a hug, he asked, “Are you sure?”
Without even looking at him, I said, “Yea, I probably need to get home.”
Know I was still living at home, he said, “Okay,” and as I gathered up my clothes, snd quickly got dressed, Jim grabbed his robe and put it on.
Eventually, he sat next to me and as bent over tying my shoes, he put his hand on my back and said, “That was really nice.”
He was looking for a response that told him I was okay with what we did, but I just wanted to get out of there, I didn’t want to stay. Standing up to leave, I said, “Okay, I’m gonna go.”
He ended up following me, and as I headed toward the front door, he stopped me and said, “I had a good time,” as he again put his hand on my back. He was again hoping I’d say the same thing, but when I didn’t, he dropped his hand off my back and before I opened the front door he asked, “Can I see you again?”
Again, I didn’t say anything right away, but feeling he wasn’t going to let me leave, feeling obligated, I smiled and simply said, “Yea, maybe.”
I’m sure he had to know I was having conflicting thoughts about what had happened, which I was, and after leaving, I continued to worry about him having cum in me.
Quickly hurrying home, I continued to think, “Why didn’t I make him use a condom,” but it was too late now and wanting to know what I might have missed in his profile, thinking, “Why didn’t I know he was gay?”
Looking through his profile again, there it was. Yea, he had listed that he was straight, but it also said he was curious. It didn’t actually say he was gay, but I think he was using the “Curious” tag to gain the confidence of guys that might be feeling the same way.
We did end up keeping in contact for a while, and he continued to suggest that we meet again, but I always made an excuse to not to meet up, and maybe I should have.
I immediately started dating girls, looking to have sex, which I did a few times, and even gad a long term relationship with a girl, however I continued to think about what happened, how it felt, and especially all the attention Jim had given me, and mostly I thought about how it felt to have him fucking me, and that he had cum in me too.
Obviously, this encounter continued to be on my mind long after it happened. It was my first experience with sex, and because of that, I’ve had serious thoughts about wanting to reach out to him to do it again.
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