Losing My Virginity, Fateful Encounter in High School

Yea, I'm sure we have all masturbated and maybe even experimented at a very young age, looking at pictures or watching videos and thinking about having sex, but whenever I find myself remembering this time in my life, and my thoughts slip back to when it all happened, I wish I could somehow go back and relive it, but afterward wish it had never happened.

This story took place when I was in my first year of high school, and like everyone, I was trying to find myself. However, I soon ended up skipping classes to hang out with my friends at a local game room that was by the school. I was enjoying not going to class and because I was spending so much time at the game room, hanging out with friends, it didn't take long before I became good friends with a guy that I thought worked there.

His name was John, he was friendly, had dark skin and dark hair, and was probably 10 or 15 years older than me. Over time, I found out he was the owner of the game room, and it only made sense because there were other younger guys that worked there.

A lot of students liked hanging out up at the game room during the day and sometime, even into the night, and on weekends. When you first walked in, it was a record shop, but there were also pinball machines that lined the walls, along with other video games, and several foosball machines in the middle.

At first, I really didn't take notice of John, but I think he must have been watching me, noticing how much time I was spending there. He was very friendly and I thought he was nice because our interactions were all very innocent and our conversations were nothing more than a casual, "Hello," as I entered the game room or asked for change.

We were becoming good friends, and I think at some point, John must have decided to see if he could encourage me to have a relationship with him.

I was so naïve and had no idea he was gay, however it would soon become apparent. As my friendship with John grew, he started giving me free games on the pinball machines and even asked me to go out for breakfast and lunch with him. When he first suggested we go out for breakfast, I was reluctant, but eventually he convinced me it would be okay.

I was actually enjoying skipping classes to hang out at the game room, and I did liked the attention I was getting, especially when he would ask me to go out for breakfast or lunch, which had become more and more frequent.

Our conversations were very innocent, at least it seemed that way on the surface, but as I think back, I am quite sure he was always looking for an opening, wanting to find out if he could get me to sleep with him.

There's one particular day that stands out and I think it was a turning point in our friendly relationship. It was a time we were out for breakfast one day, when our simple conversation turned to one about sex and girls.

John asked, "Have you ever been with a girl?"

At the time, I had been with several but I had not gone all the way. Trying to act cool, not wanting to let on, I enthusiastically said,"Yea."

It made him smile and as we talked about what hair color we liked, and kind of boobs, and asses, etc., we jokingly laughed a little. However, when John happened to ask me when was the last time I had sex, I pause, and then inadvertently let it slip that I had never actually had sex.

He was shocked a little but asked, "Why not," and after a few seconds John continued by saying, "Maybe you like guys."

Quickly snapping back, I told him, "No, I like girls, not guys."

John then smiling said, "Then why haven't you done it yet?"

Pausing, I told him that I just hadn't had the chance. Our conversation had taken a turn and after another little pause he asked, "Do you ever find guys attractive?"

This line of conversation made me uncomfortable and without hesitation I said, "No." John, looking at me continued the questioning by saying, "So, you mean that when you're watching a movie and there's a guy in it, you never say to yourself, hey, he's good looking."

Again I said, "No, I never think that way."

Seeing the topic made me uncomfortable, John chuckled and quickly calmed me down by saying, Don't worry," and then agreeing that I only like girls, our conversation seemed to be more innocent again, but it was about to take yet another turn.

As the conversation paused again, John asked, "Is everything was ok?"

When I nodded my head, John smiled and then told me that he enjoyed my company saying, "It's really nice to have someone like you to talk to."

I agreed by again nodding, which gave John time to gather his thought to hopefully steer the conversation in a direction he was looking for. John now subtly told me he was sorry if I was embarrassed, and as I nodded my head, I told him it was ok.

John, smiling said, "Good," and proceeded by again saying that he understood that I only like girls. Nodding my head yet again, John subtly said that he liked girls too bet then casually mentioned he was bisexual. Looking at each other there was a pause and then seeing my puzzled look, he asked, "Do you know what that is?"

I had never heard that word before and after I told him, "No, I didn't," he seemed to relish the opportunity to explain that yea, he was attracted to girls but that sometimes he found guys attractive too.

Smiling, looking for my reaction, he continued by saying that he did like having sex with girls but sometimes if he found a guy attractive and they hit it off, he liked sleeping with them too.

I was shocked, and not knowing what to say, I nervously sat there. John now continued the conversation by asking what I thought about it. I didn't know what to say or what to do, so I simply told him that I wasn't sure.

The conversation again paused awkwardly for a second, and John must have seen the topic made me uncomfortable, because he now said, " You've been a good friend, I'm glad I was able to tell you."

I hesitated but politely acknowledged him with a cautious nod and smile. It still made me nervous and when he continued by saying, "It's really nice to be able to hang out with you," I naively smiled, but didn't look at him.

In a weird way, it was kind of nice to hear he liked hanging out with me and it did put my mind at ease, because I liked being with him too, but the thought of sleeping with another guy was definitely not what I would ever consider.

We didn't say anything for a minute or so, but I could sense John was searching for something to say. It really started to make me nervous and when he said, "I don't want to embarrass you," I looked up.

He was smiling and then as he reached his hand across the table he said, " I wanted you to know," and then as I looked over at him, John subtly said, "I'm really attracted to you."

"Oh my god," I thought, "what was he saying?"

Continuing to cautiously look at him he revealed, "I don't know if you're open to it, but I've been thinking about asking you to come over to my apartment."

A sudden uneasiness came over me about the conversation and after another pause, I think he realized it. I didn't know what to do; this man was my only way back to school, but then trying to break the tension he said, "Don't worry, I'm not going to do anything unless you want to."

Thinking to myself, "He just suggested I come over to his place, because he wanted to sleep with me," and the thought, of being alone with him was troubling.

It was obvious that John wanted me to know how he felt, but it left me speechless and I think he knew the subject was making me nervous.

Feeling he had overstepped, he said, "Come on, let's go," suggesting it was time to leave.

Looking up, relieved to be going, I couldn't help but smile. He had shown his hand and as we left the restaurant, heading back to the game room, he pressed the issue a little more by saying, "I hope you'll think about it."

Yea, I was probably curious being he had built up our friendship and I know he was hoping he could somehow convince me to go to his apartment with him, but deep down I felt it was wrong.

Again, I didn't say anything, and as I looked out the side window, John blurted out, "You've been such a good friend," and then said, "let me get you something."

I hesitated, nervously thinking,"What was he saying?"

Sensing him looking over at me, waiting for me to answer, but when I didn't, he boldly asked, "Is there anything you want?"

He wasn't going to let it alone, so I simply said, "I don't know."

The rest of the way back to the game room, I was quiet, but as we pulled into the parking lot, he said, "Please think about it, okay?"

I wanted to get out of the car and get away from him, but as I opened the door he quickly said, "Don't forget to tell me what I can get you."

Politely smiling, I said I'd think about it, how could I not. John had basically just said that he wanted to have sex with me. It didn't sit well with me at the time, but I did think about it.

A couple days later, I did venture back to the game room to hang out with friends, and seeing me, John of course approached and asked if I had thought about his offer.

I told him that I had thought about it but said, I'm not sure."

Realizing he might have convinced me, he said, "Come on, let's go get something to eat."

I felt pressured to go and in the car on our way to the restaurant, he asked, "What is it you would really like to have?"

Hastily telling him,"Nothing," he was now hard-pressed to get an answer.

John again asked, "Come on, there has to be something you would really like to have," and then said, "I wanta get you something."

At the restaurant, we didn't really talk about much, but I felt that he wanted to continue to find out what it would take to get me over to his apartment, because he continued to pressure me.

There was one thing I really wanted and when I eventually told him, "I really want a car," he seemed to be dazed.

Yea, I really wanted a car but I said it hoping he'd somehow realize I didn't want to go with him to his apartment, but suddenly he grinned. Right then I thought,"Oh my god," I had just given him the opening he was looking for.

Pausing, he then excitedly asked, "What kind?"

Nervously, I told him I wasn't sure, but he needed to get an answer so he kept probing to know, saying, "Come on, there must be one you're really thinking about."

He had definitely sparked my interest and he knew it, but I again told him I really wasn't sure. I never thought he would actually get me a car and so I wouldn't have to commit to going with him, but he didn't want to lose this chance, hoping to get me in bed.

We eventually left the restaurant and as we were driving back to the game room, he said, "Let me know what kind of car you want," and then continued by saying, "I'll see what I can do."

For some reason I felt okay with this conversation, because naively I thought he had just said he'd get a car for me. I was so excited to have a car and foolishly convinced myself he'd get one for me, no strings attached.

All I was thinking about was having a car, I wasn't thinking that I would be giving him the opportunity to have sex with me, and it probably wouldn't be just once.

When we pulled into the parking lot, he reminded me to let him know what kind of car I would like, and when I said I would, he immediately asked if I would be able to tell him tomorrow.

Hesitantly, I told him I would try and as we got out of the car and went inside the game room, we went our separate ways.

He had really got me thinking about what kind of car I would like to have and as I thought about all the different kinds, I wasn't thinking about what would happen if I actually went through with it and told him.

I was torn, not sure what to do, but the next day when I went over to the game room, there he was. Seeing me, he immediately came up and asked if I had made a decision. I wasn't sure how to answer, or if I should, but eventually said, "Yea."

Smiling John simply said, "Great, let's go for a drive and you can tell me!"

Even though his response was somewhat reserved, it was obvious he was excited, and as we pulled out of the parking lot he asked, "Okay, so what is it."

I was nervous to say anything, but when I told him what I wanted, he smiled and excitedly said, "Okay, I'll start looking, but it might take me a little."

It was out there now and I became very excited to have a car, but again I wasn't thinking about what he would expect in return. A week or so went by, and then while I was up at the game room, he came up to me and casually said, "Hey, I found the car."

I was shocked but anxious too and when he suggested we take a drive, I couldn't believe he had found it already. He was really good at pumping up the situation, and in the car, he said he had seen it, and said it was really nice.

John could obviously see my excitement and continuing the façade said, "All it needs is to be cleaned up a little," and then he told me I could probably have it in a week or so.

I was so excited to see it and drive it, but now John had a question for me. I should have known but when he said, "Well, since I found the car, do you think you'll come over to my apartment now?"

I didn't know what to say and in all actuality, I knew there was going to be a catch to this whole thing. After a short pause he said, "I'll tell you what, you come over to my place with me tomorrow afternoon and try it, if you don't like it, we'll stop and you can still have the car, what do you say."

Apprehensive, I didn't say anything and when we returned to the game room, he said, "Why don't you think about it and then come by tomorrow and let me know what I want to do."

I was eager to have a car but worried about what would happen at his apartment. Yea, I was a little curious, and reminded myself that he said I could have the car if I decided not to do it with him.

That night, all I could think about was the car he promised, and subsequently convinced myself it would be okay to go through with it.

The next day, I nervously went up to the game room around noon and tried to avoid him.

However, the minute he saw me, he came up and casually asked, "How is it going?"

Telling him everything was okay, he asked, "Are you ready?"

Hesitant, I paused but then simply nodding my head I said, "Yea."

John too smiled and then asked, "Are you sure?"

I again told him,"Yea."

Ushering us out to his car, we headed off to what I suspected was his apartment. I really wasn't exactly sure where we were going, but I knew where it was going to take me. Along the way, I think to break the tension, he asked if I was hungry, wondering if I wanted to get something to eat first.

Replying, "No, I'm okay," all the time thinking, "I just want to get it over with," so he'd give me the car he promised.

Eventually, we pulled into an apartment complex just down the street from the Village Inn and then parking out front of one of the buildings, he excitedly said, "Here we are."

Getting out of the car, I couldn't help but look around, to see if anyone saw us as we hurried inside. His apartment was a garden level one and once inside, it looked to be modestly furnished and very clean.

Standing there, watching John as he closed the blinds in the front room, he turned and then facing me, smiled and said, "Come on."

He had me follow him down a short hallway, towards what I figured was his bedroom. Part way down the hall, there was a bathroom on the right, and across from that was another bedroom with the door ajar.

Entering the bedroom at the end of the hall, John gestured toward the bed, telling me to go ahead and have a seat. As I sat down on the edge of the bed, he closed the door part way and then went over and closed the blinds.

The room was very spacious, obviously the master, with a bathroom toward the back, and as the blinds closed, it gradually got dark. My eyes quickly adjusted, but there was still a hint of light that manage to slip past the closed blinds. John now sat next to me on the edge of the bed, and when I nervously looked down, he patted me on the thigh asking, "Are you okay?"

Looking up slightly, I nodded, but I'm sure he could tell I was nervous because he squeezed my leg slightly and said, "Don't worry, everything'll be all right."

Not wanting to appear scared, I smiled sheepishly, and after nodding again, I nervously looked back down at his hand on my leg.

Taking his hand off my thigh now, he stood up and said, "Why don't you go ahead and take off your clothes."

Looking up at him, puzzled, he smiled and then continued by saying, "I'll be right back."

I was confused but as he turned and headed toward the bathroom at the back of the room, I sat there frozen for a moment. Watching as he closed the door, disappearing into the bathroom, I quickly thought, "He must be taking off his clothes," and realizing he'd be coming back, I figured I had better start getting undressed.

Self-consciously, I took off my shoes, my shirt, pants, and my socks, piling them at the end of the bed, but for some reason, I had decided to not take off my underwear. I don't know if it was the embarrassment of being naked, or maybe it was an attempt to save some sense of dignity, in either case I nervously sat there waiting for John to come back.

Hearing the door to the bathroom open, I turned to watch him as he came out. He was only wearing a long sleeved button down shirt, and as he turned off the bathroom light and walked toward me, I tried to see what he looked like without clothes. I was curious, I wanted to see his cock, however, being my eyes hadn't adjusted to the dark and the tails of his shirt conveniently covered him, I never got a good look.

Not wanting to get caught staring as he approached, I embarrassingly turned my gaze away from him. John now sat next to me, and then patting me on the leg again, there was a pause. He then immediately asked, "What's wrong?"

He noticed I was still wearing my underwear, but unsure what was wrong, I asked, "What?"

He must have realized I was nervous, because he quickly dismissed it saying, "Never mind," and then said, "Don't worry."

Nodding my head, I again nervously look down. John now told me to lay down on the bed, and then guiding me to turn, he stood up.

Quickly moving up and lying in the middle of the bed, John said, "Move over to the edge," motioning to the one side.

As I did what he told me, I ended up facing the wall that had the window. John now came over and kneeling in front of me, he immediately started rubbing my body, and my legs. I was so nervous and when he moved his hands down to my crotch, and told me to relax, I closed my eyes. He now fondled my cock and my balls through my underwear, and hearing him say, " HMmmm," he eventually spreading my legs. Propping my one leg up at an angle, giving him better access, he went down mouthing my cock.

Trying to distance my thoughts from what was going on, I focused on the window and the light that was creeping through. Continuing to feel on my cock through my underwear, he eventually reached in, wanting to feel my cock.

Feeling his hand on my still limp cock, desperately trying to get me hard, he peeled down the band, and then struggling to take them off, he frustratingly asked, "I need you to help me."

This comment brought my thoughts back to what was actually happening and quickly sitting up, I got them off. Casting them off the end of the bed, I laid back down and as I shifted a little, trying to get comfortable, John pulled me closer to the edge saying, "That's better."

He again spread my legs and as he started rubbing and pulling on my cock, trying to get me hard, I looked toward the window, trying to not think about what was happening.

I could tell he was becoming desperate to get me hard, wanting to suck my dick, and ultimately wanting to fuck me. He eventually did take my semi hard cock in his mouth, but because I was distancing my thoughts, I wasn't getting hard. Frustrated, he stopped sucking it and looking up at me as he continued to stroke it, he asked, "Does it feel ok?"

This again brought me back to what was actually happening and when he asked me to try to help him get me hard, I hesitantly agreed. It made him smile and as he again started jerking me, I knew he wasn't going to stop until he got me to cum. Closing my eyes, I tried to concentrate on getting hard and when he again took my cock in his mouth, sucking it, I thought about wanting to cum.

I had never had my dick sucked before, and yea, I had thought about what it would be like and as I really tried to get into it, it actually felt good. My cock gradually started to get hard and as he continued to suck and rub it, I felt as though I was about to cum.

I wanted to cum, but suddenly becoming self conscious, thinking I needed to be all the way hard first. Trying to hold back, not wanting to cum yet, my cock started to get soft and I think John could sense it too.

"I had to focus," I told myself, "I needed to cum whether I was hard or not."

Trying to concentrate again, I closed my eyes and thought about cumming in his mouth. Purposely bucking my hips a little, trying to move my cock in and out of his mouth, I again felt I was going to cum.

I wasn't hard, but not wanting lose it, I pushed into his mouth and let it go, cumming prematurely. It surprised him a little I think, but as my cock jerked in his mouth and cum dribbled out, John stopped sucking. It felt good to cum and as he continued to milk it while still in his mouth, I felt my cock going limp almost immediately.

John seemed a little disappointed, because as he stopped he asked," Is that it?"

Instinctively, I looked down and questioningly I asked, "What?"

Wiping his mouth, he smiled and quickly said, "It's okay," and then asked if it felt good.

Smiling, I nodded yes and then as he proceeded to get up off the floor, he told me to move over to the middle of the bed. Quickly sliding over as John moved to the end of the bed, I tried to position myself, laying more or less in the middle.

John was now directly behind me and feeling him leaning against the bottom of the bed, he said, "Go ahead and get on all fours."

I wasn't sure what he meant and when I didn't do it right away, he said, "You know, like a dog."

Amused in a way, I smiled, and as I did what he said, I asked, "Like this?"

John didn't say anything right away, obviously delighting in the thought of fucking me, but then he remarked, ""Why don't you move up a little."

Inching my way up toward the head of the bed a little, I felt him climb on the bed behind me. He was on his knees and as he moved closer, he spread my legs apart with his knees.

Reaching above me, to one side, he pulled a pillow out from under the covers and putting it in front of me, he said, "Put your head down."

Smiling cautiously, I didn't really think he meant it, but when he pushed on my back, forcing me, I put my head down. Sliding my hands under the pillow and turning my head to one side, I could feel as though my ass cheeks willingly spread a little.

I felt so vulnerable, especially with him behind me, and when he gently started to rub my back and my ass, making sure to spread my ass cheeks occasionally, I really felt self-conscious, knowing what was about to happen.

"You're really tight," he said, "you're going to need to try to relax."

Spreading my legs a little more, I heard him flip something open. "What could it be," I thought?

However, as soon as I heard him squeeze something out, and then slop it on his cock, I realized it was probably KY. I now braced myself, knowing what was coming next, or at least thinking I did, I took a deep breath.

Unexpectedly, John touched my butthole, and thinking it was his cock, I rose up, scared. He immediately pushed on my back again saying, "Relax, it's just my finger."

Smiling to myself, relieved, he told me to put my head down again. Doing what he asked, continuing to naively smile as he gently spread my ass cheeks and dabbed my tight little butthole with lube, I tried to prepare myself for the inevitable.

It actually felt kind of good, but then as he pushed his finger in me, I tighten up and again pulled away slightly. He again said, "Relax," and after rubbing my ass cheeks, I took a deep breath as he again dipped his finger in my ass.

John continued to finger me, trying to loosen me up, and yea it did feel good but then as he leaned forward, and pressed against me, he whispering, "You're really tight."

Taking his finger out of me and rubbing my ass cheeks again, he asked, "Are you okay?"

I could hear in his voice that he was anxious to be in me, wanting to fuck me, which made me nervous, and anticipating what was next I said, "Yea," and giving a little nod of my head.

John moved closer and as his legs brush against mine, I nervously shifted a little. John now put his hands on my ass, and trying to steady me he asked, "Are you ready?"

Not replying right away, he said, "Don't worry," which made me subconsciously smile and reply, "Yea."

I could hear him rubbing his lubed up cock and then he quickly remark, "It might hurt a little."

I knew what was coming, but really I had no idea, and when he told me, "Try to relax," I took a deep breath.

Spreading my ass cheeks a little, using his one hand, John pushed up against me, sliding his cock in my crack. It felt good and when he occasionally pushed the head of his cock up against my hole, teasing it, I became excited in away.

I tried to relax as he repeatedly pushed the head of his cock against my butthole, obviously trying to be gentle. At first, it didn't hurt, it actually felt kind of good having him teasing my tight little hole with the head of his cock.

Continuing to try to relax, thinking about him being in me I said to myself, "This isn't so bad."

However, as John tried to gently push into me, he seemed to struggle. He knew it was going to hurt and not wanting it too, he stopped. Rubbing my ass cheeks back and forth, hoping I might loosen up he said, "Try to relax."

Giving him a subtle little nod, John again put the head of his cock against my butthole and grabbing my waist, he said, "It might hurt a little," again telling me, "Relax."

He tried to be gently, but again not being able to get his cock in me, John suddenly pulled me closer, pushing hard, forcing the head of his cock into me.

"Oh my god," the pain was excruciating! It hurt so bad, I immediately rose up and pulling away, John's cock inadvertently slipped out before he could stop me.

Squeezing my ass cheeks together, trying to ease the pain I thought, "I can't do this."

Trying to sound concerned, he immediately said, "What's wrong?"

Pausing, thinking to myself, "What's wrong," I quickly replied, "It hurts."

John paused now too and then saying, "Ok, you need to try to relax more," and then explain, "the hurting'll eventually stop, you just need to relax."

He seemed a little upset, or maybe concerned, and needing to see if I'd still let him do it, he said, "Let me know when it stops hurting."

"Of course," I thought, " he wanted to try again."

The pain eventually subsided, really only hurting for a little while, but I wanted to put him off as long as possible, hoping he might give up on wanting to fuck me.

However, after asking me a couple times, if I was ready to try again, and me telling him, "No," he eventually had waited long enough.

Moving closer again, he finally said, "Ok, let's try again," and then continued by saying, "You really need to relax, especially when I'm in you."

Reluctantly I agreed, and after again smearing a little more KY on my ass, he immediately tried to push into me. Again, it hurt, but I tried to relax, letting him do it, but it was so bad, I asked him to stop.

He refused saying, "Just relax," and hearing this I again tried to pull away.

Desperately holding me by my hips, wanting to keep his cock in me, he said, "Stop moving."

It was so painful, "I couldn't do it," and when I hastily pulled away again, and his cock slipped out again, John was visibly pissed off.

Grabbing my waist again, straightening me up, he angrily said, "Come on, what's wrong now?"

He had to know, but when I told him it hurt, he sternly said, "You, have got to relax!"

I didn't know what to say, and then in a frustrated voice, John again said, "Tell me when it's okay."

I really hoped he might give up on the idea of fucking me. It continued to hurt, but it was more of an aching now, and when John told me, "You really need to try to relax," I knew he wasn't going to stop trying until he got to fuck me.

John again moved closer and after rubbing my ass he asked, "Okay, are you ready?"

I was really hoping he'd stop, but when I didn't say anything, John moved closer, and again after dabbing a little more KY on my hole, he pushed his finger in me. I tried to relax as he fingered my ass, hoping it wouldn't hurt this time, but knowing it probably would, I tried to brace myself. John now started to push the head of his cock into me and when he asked if I was ready, he again pushed hard, before I could reply, forcing his cock into me.

Again, it immediately hurt, and I did try to pull away, but this time, he held me tight sharply saying, "Stop!"

Reaching back, trying to push him away, and asking him to stop, John said, "What's wrong?" and then sternly said, "You need to relax!"

I again tried to pull away, urgently telling him, "It hurts!"

It upset him having to hold me, but trying to keep is composure said, "Okay, I'll stop, but you need to quit moving."

Trying to relax as John continued to hold me by my hips, knowing he wasn't going to stop until he got to fuck me. The pain did eventually subside a little, however as he started to move his hard cock slowly in and out of me, it again hurt as he progressively pushed into me a little more.

The pain immediately returned, it hurt so bad, and trying to get loose I thought, "He had to be big."

Reaching back again, pushing on his thigh, asking him to stop, he grabbed my waist, pulling me close. He did stop and as he held me, he questioned if I was okay. I again told him it was hurting, asking him to stop.

Continuing to hold me, he again said, "Relax, the pain'll go away."

I knew he wasn't going to stop, not now, and when I tried to wiggle free again, John, pushing on my back, stopped me, forcing me to keep my head down.

Clinching a handful of sheet under the pillow as he slowly starting moving his cock in and out again, I tried to relax. It still hurt but it was tolerable and knowing I needed to let him finish, I tried to distance my thoughts.

Holding me by my hips and guiding me to slowly move back and forth as he started to fuck me, I could hear his cock going in and out of my sloppy hole.

It really felt big and as he continued to move us in unison a little faster, my cock started to get hard. The pain had definitely eased, but then he suddenly stopped. I sensed he was frustrated and when he tried to explain that I need to help, I didn't understand what he meant.

John quickly tried to explain by saying, "I needed to move back and forth with him," and then said, "Like this," as he again grabbed my hips. Pushing and pulling me back and forth, and back and forth he said, "That's it, keep going."

I tried to do what he asked, it still hurt and when I happened to try pushing his cock out, thinking it might help, the aching went away.

I couldn't believe it, it actually felt good, and hearing his body slapping against my ass as he fucked me faster, it obviously had to feel good for him too.

John now pushed down on my ass, wanting me a little lower, wanting to more easily fuck me. He then asked me to arch my back up, again to better position me. I now hoped he'd finish, wanting to be done, and I wanted him to cum. when he reached around and as he started rubbing my now hard cock he remarked, "Yea, that's it."

John eventually quit playing with my cock and straightening up, he grabbed my hips, and focused on fucking me. Hear his cock sloppily going in and out of me, I tried to match his thrusts, but they became quicker, more deliberate, and when they became a little erratic, I couldn't keep up.

His breathing had become more labored, and knowing he must be close, I rocked back and forth accepting it, wanting him to cum. John then gave a couple focused thrusts and then pushing deep into me he stopped and said, "I'm cumming."

He pushed too deep, it hurt, I tried to pull away, but he held me close saying, No, don't!"

He was out of breath, but as I ignorantly tried to keep moving, John abruptly said, "Stop moving!"

Stopping, I could feel his cock jerking faintly inside me, and realized he had cum. John felt on my ass briefly and then hunching over me slightly he asked, "Are you okay?"

I didn't say anything, I was scared that he had cum in me and as John subtly started moving his cock in and out of me again, I could feel something seeping out. Pushing me to my stomach, and giving a couple quick little thrusts, he slowly pulled out. Kneeling between my legs, he gently rubbed my ass cheek, and then spreading them, he obviously wanting to see.

I was glad it was over and when he said, "That really felt good," I felt he get off the bed.

Continuing to lay there, not knowing what to do, he told me, "You should probably go clean yourself out."

I didn't know what he meant but when he said, "You can use the bathroom in the hall," I quickly slid off the bed.

He had started toward the bathroom too and as I hurried out of the room he told me to come back when I was finished. In the bathroom, relieved it was over, I wasn't sure what he meant by cleaning myself out. I felt as though I need to poop, but when I sat on the toilet and tried to push out whatever was inside, I did manage to push out something, but "What was it," I thought!

Wiping, I looked at it again thinking, "What is this?"

After trying to push out more, I stood up and looking in the toilet, I could see some was floating and some had sunk to the bottom. It was white and thinking it must have been the KY that was floating and ... "Oh my god," it was his cum that sank.

I was scared, "What had I let him to do," I thought.

After a few minutes, I decided I had better go back, and as I regained my composure, I made my way back to the bedroom. It was kind of dark and not seeing him right away as I entered the room, I became a little anxious. However, John approached me and as he gently guided me to the bed he asked, "Are you okay?"

"Of course I was okay," I thought, "why wouldn't I be?"

Nodding my head, we eventually sat down on the edge of the bed. He didn't say anything for a moment and when I happened to look over at him, he was smiling. Smiling too, John said, "Why don't you get back on the bed."

"What, why," I thought, "he wants to do it again, what was I going to do?"

Turning me slightly, coaxing me to get back on the bed, I hesitated. John stood up now and as I reluctantly got on the bed, crawling on all fours, he too got on the bed right behind me.

I didn't understand, "How is he able to do it again, I thought, "how can he be hard, he had cum just a few minutes ago?"

John again instructed me to put my head down, and as I did, he immediately moved up, and spreading my legs, he again dabbed some KY on my butthole. It made me tense up and as he teased it a little, eventually pushing his finger in me, I tensed up again. It did feel good and I hoped this was all he wanted to do, but when he again said, "Try to relax," I immediately thought, "I don't want to do it again."

I decided to try tightening my ass, not letting him penetrate me, however, the minute he tried to push into me, his cock seemed to slip in more easily than before. I couldn't stop him, I didn't want to do it anymore, but he was in me and as I searched for what to do to stop him, I decided this time I wouldn't help.

"Oh my god," he was fucking me again, and even though I tried to not help, it actually felt good, but I told myself, I wasn't going to help.

Immediately noticing I wasn't helping, he stopped and asked, "What's wrong?"

I hesitated at first but told him that I thought we were only going to do it once. Pausing, he reached under me, and as he took hold of my cock, fondling it he said, "Come on, I thought you liked it."

Feeling dejected, I again didn't saying anything. John now aggressively grabbed my hips and said, "Let's do it one more time."

Immediately, John tried to forcibly fucked me, moving me back and forth, he obviously wanting to cum again. It did feel good, but as I continued to think to myself, "He had told me we would only do it once."

I could tell John was becoming frustrated and when he again said in an out of breath voice, "Come on," I made sure to not help.

Discouraged he eventually stopped, and pulling out hastily, he got off the bed, saying, "Go clean up and get dressed."

He quickly disappeared into the bathroom, and hurrying out to the hall one, closing the door worrying, "What's next.?"

Quickly wiping the KY from my ass, I hurried back into the bedroom and started getting dressed. As I sat on the bed continuing to out my clothes on, he came out. Not looking at him, as he again sat by me, he eventually asked if I was okay. He tried to sound friendly now, hoping I might want to do it again, but when I didn't say anything, he continued to probe by saying, "That was really nice."

When I again didn't reply he asked, Did you like it?"

Feeling he had ruined his chance to have sex with me again, John desperately wanted to rebuild our relationship by pressing to see if I liked it.

Continuing to not say anything, I felt powerless, he was my ride back to the game room and when he asked again if I liked it, I finally said, "Yea," so he'd stop pushing for answer.

We eventually left his apartment and as we drove he suggested that he take me home. Hesitant at first, I agreed it was a good idea, not really wanting to see or talk to anyone after what had just happened.

I wanted to get home, I wanted to get away from him, and feeling John continually look over, obviously wanting to say something, I tried to focus on looking out the side window, not wanting to make eye contact.

The ride seemed to be taking forever, and when I felt the crack of my ass becoming slippery, it reminded me that it was probably KY oozing out, and panicked that it was most likely cum too.

Finally pulling into my cul-de-sac and parking out front of my house, John reached over and touching my leg again said, "That was really nice."

Looking over at him, I smiled, relieved, and after quickly getting out of the car, and not looking back, I hurried in the house. Inside, I went straight to the bathroom and after taking off all my clothes, I sat on the toilet. I wanted to get his cum out of me and pushing, I only managed to get a little more out.

Deciding to took a long shower, thinking I might be able to somehow get the rest out, I desperately fingered my ass. Not being very successful, I eventually convinced myself, "Yes, I had probably gotten it all out."

Drying myself, I went to my bedroom and as I sat there, I felt ashamed about what had happened. Continued to mull it over, realizing he hadn't use a condom, and that he had cum in me, I worried myself into a frenzy about getting a disease, but it was too late now. I did continue to worry about it for a long time, and eventually did get tested, but much later.

A few days went by before I got up the nerve to go back to the game room. I wanted to ask about the car he had promised me and when I confronted him about it, he smiled and said, "Let's go for a drive and talk about it."

Leaving the game room, I was confident, he'd agree to give me the car, because I felt I had fulfilled my obligation by letting him fuck me. However, as we pulled away and drove around, he explained, "The deal was, that you'd sleep with me," and then said, "I was hoping we'd do it one more time."

I was kind of confused, and when John said that I hadn't done my part, I was in shock. There was a paused but then he said "Well, if you want to do it again, I can give you the car," but then said, "But only if we do it again."

I didn't know what to say, I wanted the car, but didn't want to have sex with him again, it was the fact of the matter. We eventually made our way back to the game room and as I started to get out of the car he reminded me again, "I still have the car," and then said, "If you want to try it again, I'll give it to you."

I stayed away from the game room for a long time and when I did return, we were cordial, but I felt he was still looking to continue the relationship. Maybe in a way I was too, but as he now happened to mention he was moving closer to where I lived, it sparked my interest. Seeing my reaction, he told me, "You should try to come by sometime."

The apartments where on the other side of my neighborhood and I did visit once telling myself, "Maybe the car is there."

I do, however, think that deep down I wanted to have sex with him again, but being I was kind of shy, I think subconsciously, I needed him to initiate it. Entering his apartment, an immediate feeling of uneasiness came over me, I felt trapped.

He kept this apartment dark too and when he tried to get me further into his apartment, I nervously told him I couldn't stay. I think he was disappointed, but if he would have just ... anyway, I left.

I did visit again, subconsciously hoping he'd make a move or offer me something, but he never did. I think he was torn, I knew he wanted to do it again, but maybe he felt I should initiate it, not realizing I wanted to do it too.

The car never did materialize, and even though I continued see him up at the game room and later tried to contact him, we never again had sex. I have continued to think about John, wanting to try it again, but these days, it could have deadly consequences.

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