I lost my virginity and learned to orgasm

This is the true Gay sex  story of how I lost my virginity and learned to orgasm.

When I left home to go to university I was very sexually inexperienced. I didn’t know how to give myself an orgasm and so the most exciting time was waking up to a wet dream. I had never been with a guy or a girl but would lie in bed rock hard thinking about some of the men I found attractive and what might happen. It wasn’t very exciting as I didn’t know what to do. I guess I was lame.

When I got to university campus I was lucky enough to get a room in the brand new hostel. It had an attached bathroom and a telephone in the room. Knowing nothing I thought that was normal. Seeing what others had, it was not. I wanted to try things I hadn’t done before so I had decent stories to tell school friends. This brings me to my learned fettish and the older man.

I went to the university gym when it was quiet during the week to work out. I hoped that a better body would get me a better sexual partner. I quite liked being in the mens locker room. The thought of these fit bodies wearing very little was a turn on. I found out that I like the feeling of wearing swim trunks (speedos) and would wear a pair to the gym and shower in them, usually erect. No one was ever there at that time so I was being braveish. One time I was in a toilet cubicle and reading some messages on the wall; there aren’t many. There is one that I like and sounds genuine. Firm older man wants younger call Jackie. The number is written below and a date. It’s a local number and added in the last month. I memorised the digits and wrote them down when I changed clothes.

I spent days thinking about phoning. Could this guy be something I would like? Eventually after a few drinks I called the number. A man answered and I asked for Jackie.

“This is Jackie.” The man replied. My heart is pounding. “I got your number from the university gym” I tell him. “Oh right so you were in the showers then?” He asked. This confused me as I had never noticed it anywhere other than the toilet. “No,” I said “it was in the toilet cubicle.” There was a silence for a short time. I thought about hanging up. “Just checking, I get some abusive calls.” He tells me.

He opens up after this and we have a fairly normal conversation. I tell him I am 18 and at the university. I describe myself as 5’8″ with short dark hair, slim build but firm and not much body hair. He tells me that sounds lovely and gives me a brief description of him, as 58, 6’1″ with black hair lean with some muscle. He tells me that his cock is thick, cut and 7″ long. I didn’t get why that was important. We talk more about how he had met other boys like me and they enjoyed his time. I was getting an erection as he spoke and I liked it. I asked where the other boys were and was pleased with his response that they graduated and left or got partners and stopped seeing him. I told him about my fetish for wearing swim trunks. He agreed that they were nice to wear and would like to see me wear a pair. At the end of the conversation he asked me to be in the gym at a certain date and time, which I agreed to. He was going to be there but wouldn’t introduce himself. He wanted to see me and said I should wear swim trunks in the locker room so he would know. I said I would have my red pair on. I finished by giving him the phone number for my room.

That day I made sure I was in the locker room at the exact time he said and stripped to my red swim trunks. I walked about to the toilet and back. I passed other guys going to the toilet and the showers that were naked, in just underwear or with only a towel but none looked in their late 50s to me. I completed my workout and repeated the walking about again after and in the shower. I still hadn’t spotted him. Not that I really knew what I was looking for.

That night he called me and said he had enjoyed the show. How had he seen me? He asked if I still had the swim trunks in my bag. I said yes and he asked me to strip and put them back on. I did as he asked. I sat in my room in my damp, red swim trunks on the phone and was enjoying it.

Jackie asked me to feel myself through the swim trunks and stroke my cock and balls. I did as asked and enjoyed it. I was very hard under the material and leaking precum. He asked me questions as I touched myself.

“Would you like my hand stroking you now?” he asked. “Yes.” I replied.

Then he said he wanted to lick my swim trunks and my hard boy cock. I was so turned on. He wanted to feel my body all over and rub his against mine. I was beyond hard and very wet. He told me to rub my trunks up and down my shaft and not stop. He wanted to hear me moan. I did as instructed. I had never masturbated correctly or enough before to orgasm but this time I had a man guiding me and turning me on. I felt so good and couldn’t believe I was doing this. As I stroked more and harder and faster I could feel that wet dream sensation. My muscles tensed and a hot feeling raced through my body. My legs started shaking and a sensation to piss myself came on. I moaned down the phone as I orgasmed into my trunks. First a hard spurt, then an enjoyable one then a set of calmer spurts.

Jackie said it sounded good. I said it was and it was the first I had given myself, thanks to him. He told me to not take them off and sleep in my damp cum stained trunks all night and to phone him the second I woke up in the morning. I agreed and with that, hung up and slept in my trunks.

In the morning I woke up fully erect in the trunks. I called Jackie as asked. He was pleased I had done so. “Have you been to the toilet yet?” He asked. “No,” I said “you said to call immediately. ” He said I was a good boy and that he was going to enjoy his next instruction. As asked I brought the phone through to the shower room and stood in the shower in my trunks still erect. Jackie told me to relax, listen to him and do what he said.

“I want you to piss yourself in your trunks.” he ordered. I was taken aback. “What?” I asked. “Do as I say boy, you won’t regret it.” Seeing as he had helped me orgasm I assumed he knew what he was doing. I stood there in the shower and relaxed. Eventually I could feel it getting closer. The sensation was quite pleasant as the piss started to drain out of my hard penis. Soaking my trunks. He was wrong. It felt good. I did like this and told him down the phone. I wasn’t mad about the piss trickling down my legs so Jackie told me to switch on the shower and enjoy the just the pissing sensation. I did as asked. I put down the phone and finished soaking my trunks in the shower.

When I finished and picked up the phone Jackie asked if I was free today as it was time we met. I so wanted that but was terrified as I well. I said I was not busy after lunch. He said he would come to my room but there were conditions. He did not wish to be identified as he was not out and wasn’t going to be. When he arrives I am not to look at him. I thought this is a bit weird as he can see me but I can’t see him. Regardless I was intrigued and agreed. He would be over at 2pm and would be wearing my red trunks only when I answer the door and I would not look at him until told to do so. I give him the address, room number and directions.

Once again I am wearing my red swim trunks. They are crisp on one side from when I ejaculated the night before. They smell of piss from this morning. They are still a bit damp from the shower. I stand around waiting for the door and there it is. My heart is racing now. What if he just wants to beat me up? What if he is a psycho? What if….. I just answered the door. I opened it slowly and asked who it was.

“It’s Jackie.” He said. “Close your eyes and open the door please.” I did as asked. He pushed in passed me and I closed the door. “Can you lock the door?” He asked. I locked the door and continued to stand there facing the door with my back to him and my eyes closed. I could hear a zipper being used and some rustling. Then he said I could turn round now and open my eyes. I did as asked.

When I opened my eyes I saw this tall man in front if me. He had taken his jacket off but was clothed otherwise and had put on a ski mask. I could see his brown eyes and mouth but the rest of his face was covered. I could not tell you the colour of his hair for sure. Jackie walked over to me and shook my hand.

“Pleased to meet you finally.” He said smiling. He had a nice voice. Better than down the phone. Did he whisper down the phone? “I’m glad to see you too.” I respond. “Where is you shower room so I can change?” he asks. I point him towards the only other door in the room beyond the one he just used and he goes in with his bag. I hear him removing his clothes and wonder what else he is doing.

The shower room door unlocks and he emerges wearing just the bike mask and a silver pair of swim trunks with two narrow black bands on either side at the waist band. His body is nice to look at. He is tall and slim and lean and he does have biceps and pecs and muscle legs. He doesn’t have abs showing but his torso is flat. He has dark hair across his chest but not very much at all. I am very pleased to see it. “I’m going to do things with you and you’ll get to have more orgasms if you do them.” He tells me. “Okay. Yes.” I say back. “From now on I want you to say yes sir or yes master.” He demands. I nod. “Yes master.”

He walks over to me and starts touching my body. “I want to feel you, like I said on the phone. Just allow me to.” He said. “Yes master.” I respond. I am turned on by this so much. My cock is hard and bulging in my trunks. He is very rough with me. His hands rub up and down wherever he wants. He rubs down my back and between my ass cheeks. He circles my ass with a finger. With the other hand he moves down my front and teases a finger under my waist band, before grabbing my covered cock. “This is very hard boy.” He is still smiling. He continues to grope me and then starts licking me. He licks my nipples and torso, going lower. He presses his face into my swim trunks and inhales. “Someone wet themselves as instructed. Good boy.” He said. His face feels great pressed against me. He lowers my trunks and my cock pops out right at his mouth. He takes it into his mouth and begins to suck me. I am moaning in pleasure. His fingers start sinking deeper between my ass cheeks taking trunk material with them. I feel him probing at my asshole as he sucks more. I had never felt anything like this.

He stops sucking and covers me back up. “Don’t want you too excited too early.” I didn’t know what he was getting at but went with it. “Get on your knees boys and do the same to me now.” He demanded. I dropped to my knees, “yes master.” Saying that was so nice. As he instructed me I rubbed my face against his trunk covered crotch. I licked the material and sucked at the position of the head of his now erect penis. I took out his cock and took it into my mouth. I sucked at the head and swirled my tongue around it. I took in more meat as the ‘deeper’ instruction came.

“Yes boy, suck your masters cock. Take it all in.” He moaned. I took more and more. I was struggling and beginning to gag. “Stop.” He said. I looked up and let go of his cock. “I’ll take control and you just suck.” Before I could respond with yes master he rammed his cock half way in and grabbed my head with his hands in either side. He started pumping back and forth as I sucked. He moaned constantly, saying how sweet my mouth was and that I should take his cock. I just knelt there with him pounding his cock into my mouth, never too deep that I gagged. His breathing and moaning changed as he went a bit quiet. His ramming got faster and he clamped his hands onto my head really tight before ramming his cock deep into my throat. He started calling me a slut as I could feel a liquid at the back of my throat. I was gagging but still rock hard in my trunks. He pulled back after a few seconds. “Swallow!” He demanded. I did as asked.

He took me to my bed and we lay down. Again he started touching me and rubbing my shaft through my trunks. We did this for ages but I loved it. Again his fingers probed my asshole and he said he was going to see to that. God knows what that meant. “Do you have other swim trunks you use?” He asked. When I responded with yes he rolled me over and ripped a hole into the back of red ones. It wasn’t big and i wasn’t sure why. Then his fingers had nothing in the way. He said to stay and that he was getting something from his bag. I lay face down on the bed with my legs apart in my ripped red trunks smelling of piss. He returned and got on top of me. I could hear him opening things and then feel his fingers very cold pressing against my asshole. I realized they weren’t cold but wet as he rubbed. He added more and more liquid. It could feel it running round to my testicles and base if my hard cock. Then he pushed harder and a finger slipped into my ass. It wasn’t sore at all. It felt strange though. I wasn’t used to someone being with me, behind me or in the same room as me whilst I felt like this. He moved his finger in and out. I moaned. Then more pressure as another finger went in too. “I’m going to massage your prostate now.” I had no idea where that was or what he would do but it felt great. I lay there allowing this man to have his fingers inside me. He pulled them out after a few minutes and said he would have to up the ante. Oh fuck what was going to happen? He showed me this black large bullet shaped object. “This is a butt plug and you are going to wear it for a while.” He said. “Yes master.” I responded. He slowly worked it into my ass. This was not as enjoyable as his finger. As he pushed it in my as hole felt like it was on fire. It was like it had heated up. I grinned and bared it and it passed. “Good boy,” he said “that butt plug fits in perfectly.” He got off the bed and told me to follow him. We went into the shower room. He locked the door behind us and we entered the shower. “You’re going to piss your trunks again and so am I. Then I am going to take out that butt plug and fuck you. I want you to watch me fuck you in the mirror. Once I am done I will give you another orgasm. Do you understand.” He questioned. “Yes master.” I said not entirely knowing what would happen.

He pressed me against the cold shower wall and rubbed up against me. “Soak your trunks boy.” He whispered in my ear. “Do it for your master.” With that I let loose a torrent of piss. He kept rubbing against me as my trunks darkened. He starred into my eyes and smile as he also started soaking his trunks. I turned the shower on as the smell was too much. “Now we’re ready boy.” He said pulling back the shower curtain.

I faced the mirror behind the sink and toilet and bent over as instructed. I lifted one leg and placed it onto the closed toilet lid. He stood behind me and finger at the butt plug. Removing it was also a struggle. His fingers were slippy from the lubricant and he slid off getting a grip. Once he pulled enough out it slid out like I was alone in the toilet doing what I would normally do. He sat it in the sink and turned back to me. “I’m going to put my hard cock inside you now boy.” He said placing his hands on my hips. He added more lubricant onto his fully erect cock and pushed it through the rip in my trunks and at my asshole. He pushed more and more. I could feel the same sensation as when the butt plug entered but it was easier. He told he to breathe slowly and he pushed deep inside me. Oh god it was so sore. But I loved having a man inside me. He stayed still deep inside me and stroked the front of my trunks and my cock underneath. I couldn’t believe it. I had that feeling again. The hot rush, the needing to piss. I started moaning loudly and orgasmed into my trunks. “You like my cock boy?” He asked but i knew it wasn’t a question. “Yes master, I love you’re big hard cock inside me.” I breathed back. “Now I will fuck you until I cum. Are you ready?” Again it wasn’t a question.

He pulled out and pushed back inside me keeping hold of my hips. I stared into the mirror and could see his pecs upwards to his ski mask covered face. It was so sexy. I was being fucked for the first time in my favorite trunks by a masked man. It was even sexier that i had just orgasmed in my trunks and that they were wet from the shower my piss and his piss. It hurt with every other thrust. I tried to time my breathing so it would be more enjoyable. Every time he pushed into me and I got the breathing wrong I would push out a moan. He liked it. His paced changed few times from long deep thrusts to short and shallow and fast. I got into it. “You like thus cock boy?” “Yes master, fuck me master.” He lowered his body to press against mine and out his arms right around my torso and to my shoulders. He then started pumping me deep, hard and fast. I couldn’t bear it and moaned constantly. “You duty slut.” He whispered in my ear. “Taking a 65 year old cock up your arse and in your mouth. Fucking slut. You swallowed my cum and had my piss dribbled down you. Now you want another orgasm up your arse.” He continued to plough me, seeing the pain in my face. “Yes I want your cum master.” I said. Then loads of thoughts ran through my head. Did I want his cum? I hadn’t seen him put on a condom. Oh god was he not wearing one? What would happen if he did orgasm in me without one. Wait! I thought he was 58. Oh god it felt so good and I had to get these thoughts out my head as I was losing interest. I looked back at his masked face in the mirror, it was all I could now see. He keep pounding away into me. So if he was 65. Actually I wanted him more if he was. Hot for 65. I did want this 65 year old to fuck me and cum in me. I was his slut.

“Yes master, fuck me and cum in me. I want your 65 year old cum in me.” I screamed. “Oh you fucking whore.” He said getting back up to standing behind me. He placed his hands behind his head and keep fucking my hole. “I am going to cum in you. Beg for my cum boy.” I stare at his clenched eyes and mask face. “Please master I need you cum. I am your slut. Cum in me.” He drilled deep into me and I could feel his cock throbbing. Ow! His motions were random but good. Some of his jerks hurt and he went in very deep. He settled after his orgasm was done. “I’m going to have to stay inside you boy until I stop throbbing. So you can cum again.” With that he stared pulling at my cock. He ripped open the front of the trunks now, pulled out my cock, lubed it up and thrashed away at it. I had never been masturbated by anyone else and had only just learned to satisfy myself so this was magic. He rubbed the exposed head of my cock so much I begged him to stop. It was so good I could not bare it. “Come for you master boy.” He said. It was an order. I wanted to. His great 65 year body. His pissy silver trunks. His hard cock up my asshole. His cum already in me. That was it. The rush hit me and I moaned. I sprayed cum everywhere. He kept on going right through the orgasm. I begged him to stop. “No master, please stop.” He didn’t. It was amazing. When I was done he wiped the cum on his hand over my trunks. “Was it better with or without my cock in you?” He asked. “Definitely with.”

He walked me into the shower still hard inside me. We washed together and he eventually was soft enough to slide out. I washed his body and removed his trunks to complete the job. He did the same for me.

Once we were dry he put his clothes back on and asked that I stay naked and lying on the bed. He left the lubricant, the butt plug and his silver trunks on the bed with me. “I expect you to masturbate into my trunks when I phone you next. You should piss into them every morning too. I want them used so I feel sexy when I fuck you next time. I am taking your trunks with me. You’ll wear them again when I fuck you.” With that he opened the room door out if site, pulled off his mask and left.

I lay there feeling slutty and used. I loved it. I was no longer a virgin and had major stories to tell people. I did do as he asked with his trunks and we met many more times during university until I found a partner and so we stopped meeting. I have never seen his face and do wonder about him. I still wank thinking about him. There are many more stories about him I can tell. Only he may know this is about him.

Thanks Jackie.