My first time

Awkward. That’s the word that describes my first time with another guy. And an experience that I won’t forget. We didn’t have the benefit of role models, the internet or even soft porn that might have made the encounter somewhat enjoyable.

We were just two sixteen year olds who ended up in bed together … and it was a twin bed.

We had been roughhousing earlier that day. Matt later would claim that he noticed I was aroused during the play where we were pushing each other as we headed down a hill. I still don’t believe that I was. And I am pretty sure that he pushed me first.

But let me set the scene. We were both attending a summer session at a fairly well regarded university having been selected for what was called an Advanced Placement Program for high school students who had completed their junior year. My first time being own my own. I did know a girl from my neighborhood who was also attending but I didn’t know her well. We met up a few times in the dining hall. And I was supposed to meet up an 80 year old aunt of a neighbor who lived not far from campus.

I was lucky to get assigned a single room whereas Matt was sharing his room with another guy.

I remember four of us hanging out together during the day. I don’t remember what we were doing but we were all in different classes. I had a calculus class every morning and then a computer programming class later in the morning or early afternoon. Since we were in the same dorm, we sometimes met up to walk to the dining hall.

It must have been several weeks into the session as Matt announced that he needed a place to sleep that night as his roommate was bringing a girl up to his room. There was only one resident assistant on the floor and his roommate had already scoped out his plan. Only two of us had single rooms and Matt needed an answer. He was only looking to sleep in the lounge chair for the night. I reluctantly agreed.

I really don’t believe that I was expecting anything to happen. I knew that I sort of liked guys but Matt wasn’t really my type — if I had a type back then. He was definitely nice though. I remember that he brought over his pillow and blanket for the chair. So I’m in my bed in pajamas and Matt is trying to get comfortable in the chair. He said that he was fine sleeping in the chair but I couldn’t imagine him being able to sleep and after some idle banter, I know that I invited him to my bed.

It was a twin bed so we were definitely close together. “Had you ever done anything with a guy?”, he asked. “No.” Matt said that he noticed I was aroused when we were roughhousing around. I denied it. Not only did I not think that I was aroused, it just seemed doubtful that anyone would notice through my pants.

I wish I could tell you that we had a sensual time exploring each other’s bodies and kissed passionately — but it wasn’t sensual or passionate. And we didn’t kiss. Once I was out of my pajamas, we did some basic exploration — he had the same familiar parts. He suggested a position that I later learned to be “frottage” and we humped each other to orgasm.

I warned you that it was awkward. It would be several years before my next foray with a guy.

I was probably about 11 years old, and had experienced getting "hard" for some time. But, had not experienced "cumming" yet. A (guy) friend and I started meeting after playing basketball for "experimental" sessions in an unused, and mostly dark, racquetball court at a local recreation center.

We would pull down our gym shorts and then our white, cotton underpants. Both of us would be very, very hard, by this time, and our dicks would stick straight up, almost touching our stomachs.

Our penises were very similar in "direction", although his was probably a little thicker, and longer. I remember his penis was very hard and bent almost arching back to his stomach. We both had just a little bit of pubic hair.

I remember this as if this happened just yesterday! At first, we would just rub our penises together. His penis was soooooooo warm, hard, and purplish at the head! It felt so good just touching each other's penises and rubbing them together. It felt velvety smooth, and warm.

He asked me if I had ever cum before. I didn't quite know if I ever had, but didn't think so. He said that sometimes he oozed some white, milky-white fluid after rubbing his penis for a while. I said I didn't think that had happened to me yet.

One of the times we met for a "session", I lay down on the floor, and he lay on top of me. We rubbed our hard penises together. WOW, it felt soooooo good!

We had been going for several minutes, when all of the sudden I felt like I had to pee. I got up quickly, telling my friend I had to pee. He touched the end of my penis and felt a small amount of warm, milky-white, sticky fluid. He said that is "cum", not pee. I felt it also, and rubbed it between my fingers. That was my first time!

We had many other sessions together, but later grew away from our experimental sessions as we became older teenagers.

I later had many mutual masturbation experiences with a guy cousin, who was the same age as me. We had many, many mutual masturbation and penis-rubbing experiences. He actually taught me how to masturbate, and I still use the same technique to this very day.

Awkward would not describe my first time with a school friend as it was quite pleasurable and a learning experience for me! Was around the age of 11 or 12. We did a lot of guy stuff together as we both lived on farms. His cousin had showed him how to masturbate and had given him some girlie magazines - we were in an outbuilding and he asked me if I had ever jo. Told him I hadn’t so he proceeded to show me how it was done. We both came almost simultaneously and cleaned up. The next time was after school to study. After finishing our homework we went upstairs to his bedroom to get ready for bed. We were both naked and hard as rocks when he asked if I would like to explore more - naturally I said yes. His cousin must have showed him how to do more fun stuff as he produced a jar of Vaseline which he both put on our cocks and a little on our assholes. He then told me to get on all fours and proceeded to slowly insert his cock inside - felt really good with no pain only pleasure! Then we switched and I inserted my cock into him. Within a few minutes I could feel his ass squeezing my cock and I immediately shot a load inside! It was an awesome experience! Think we met up several more times but as life got busier with girls and school we never had any more sessions together! Good memories!

Sucked my first cock today, and swallowed his cum. The experience was unbelievable. Loved every second. Only took 88 years! What a waste. Missed 50% of the population for no good reason! Men and women, each bring separate attributes to the bed,and each of them are immensely enjoyable to both genders. "Names" are designed to keep us from finding this beautiful way of pleasuring all humans. In the future, I will never be limited by a "name".

I don't think it was awkward for my first (I can't speak for him). He was my first and I was his first. Although he is a zity member, we did not initially meet here. For me, awkward was the farthest on my mind. We decided to meet a McDonalds. And my heart was pounding when I flashed him the bra I was wearing so he could see it was me. We ended up in my pick-up at a graveyard where played with each other in our panties. Then eventually, we started sucking each other until we both had a happy ending. That was quite a few years ago and since then he gets tired begging his wife for sex and I don't get any (typical post menopause problems with husbands {not all woman are like that, just ours and any older men looking for a blow job [but I digress] } ) we meet on occasion for some panty oral fun.

This is a follow up to post#4. Sucked my second cock yesterday, and happily swallowed his cum. While I still haven't been fucked yet ( is in the works), I have discovered French kissing a man is as exciting as the other gay acts I have been experiencing. It's the natural act beginning any gay sexual activity as breathing. And it feels wonderful. As foreplay, it sets the stage for the rest of your sexual acts and enhances them. When I suck my partner's cock, my only goal is to please him, and, boy do I do that! All the activities I have experienced have only led me to conclude,that I am a full homosexual, and happy with the knowledge. It is the missing puzzle piece that completes my personality, and physical body. The amazing part is, I do not feel like I have changed in any way! I am the same me, that I have always been, have the same thoughts, love the same people, etc.I am just more complete. What a change, for less than a year to accomplish, but I have!

Unfortunately I have mixed feelings about my first time. It was very exciting and most things were very enjoyable (rubbing bodies, wanking other ones penis, getting rimmed and getting fingered and a massage of prostate). But my first times of anal sex were very painful and I first regretted it ( I was 14yo and only 1.45m tall, he was barely 17yo and 1.85m tall with a huge fleshy penis). He wasn't very careful but luckily he came quickly. The first times he even wasn't able to enter his penis in my bum. He motivated me to have further and further tries to get used to his penis, and he also tried giving me a Paracetamol suppository right before. However with time I felt less pain and could enjoy as well. Nowadays I would not repeat it at that early age again.

@Danto Did he at least use proper lubrication?

My first time was extravagant and over the top

. Anyone who knows me, that moderation isn’t really my cores strength. I had a late, he was almost 18, a year older than me. He was super experienced and liked to share details about his experiences. One day we went out to the woods for him to smoke, when he whipped out his cock and said he needed badly to cum, and I should join him. With some coaxing I did, and mutual Masterbation became a regular thing for us. One day he came up and told me he met a girl who wants to fuck two guys. At first I was reluctant being a virgin and all. But he said he would take good care of me and help me out and it would be fun. So my first time was literally in a 3way. She wasn’t some girl, she was a divorced lady mid 30s that loved dirty sex. It was kinda awkward and I was a bit over phased, but all in all it went ok. We did it several times and it got better and they both taught me a lot about my body and sex.

@Danto

But my first times of anal sex were very painful and I first regretted it ( I was 14yo and only 1.45m tall, he was barely 17yo and 1.85m tall with a huge fleshy penis). He wasn't very careful but luckily he came quickly. The first times he even wasn't able to enter his penis in my bum. He motivated me to have further and further tries to get used to his penis, and he also tried giving me a Paracetamol suppository right before. However with time I felt less pain and could enjoy as well. Nowadays I would not repeat it at that early age again.

Was this also for your boyfriend the first anal sex?

If I understand it correctly your boyfriend didn‘t prepare you and started immediately with the anal intercourse. You mentioned that you were allready familiar with getting fingered and a massage of prostate and so on. These activities would be suitable to prepare especially the passive sex partner before the anal penetration. Why he didn‘t try to help you to become relaxed?

If an active man wants to penetrate his sex partner but his partner's sphincter is not relaxed, would it hurt him too?

If an active man wants to penetrate his sex partner but his partner's sphincter is not relaxed, would it hurt him too?

Tried anal penetration with my wife once, but it didn't work out. She wasn't relaxed enough and I did not find it pleasant either. So no penetration. But I had a suspicion that not being circumcised, it would have been somewhat painful on my part too, getting the foreskin really stretched down as far as it would go.

@Jacana

He used spit, so I might say: no it wasn't optimal lubrication

@passiverPatient

Interestingly no, he had some experience with two others, so he knew what he did and what he needed. But he burned in his ecstasis so he wasn't that careful to me who was green as hell.

My first time was scary. I was almost 17, he was 17. We met at a sock hop...I know many of you are like whaaa??? It was a dance in usually a local community center with a band or a DJ and everyone took off their shoes because it was usually on the wooden basketball court.

So, now that's said, I was with my gf of the time and we were having an argument. The only place quiet enough to talk was in one of the glass walled offices right off the court. After we hit a road block in our conversation she left to go back to dance. I looked over and saw the young DJ who was playing all the music in the next glass room. He motioned me over.

He was cool. He asked is I was OK as he could hear our conversation. I said as good as expected and he laughed. I told him I enjoyed his collection of music and he said I should see his low power radio station at home. He was also a local DJ in the area so I had heard him before. He invited me to come over to see his station and his collection.

He lived about 2 miles from my house so one Saturday about a week later I ran over on my Honda. He gave me the grand tour of his garage based min radio station.. which WAS a radio station, just low power. It's where he practiced. He had a HUGE collection of 45 and 78 records.. literally hundreds filling his parents living room and a spare bedroom. We chatted for hours and listened to his favorite tracks. His mother asked if I wanted to stay for dinner so I check with home and it was OK. After an early dinner he asked if I wanted to take a dip in their pool. I said I had no bathing suit, and he said he had a spare.. so we changed and spent an hour or so relaxing in his pool as it got dark. The pool looked so cool with the underwater lights on but we finally had to get out so we weren't totally eaten by mosquitoes. That's when he asked if I wanted to sleep over.

Well, I was sort of mesmerized by it all and felt so lucky to be spending any time with such a popular young DJ. Again, my parent's were OK so we headed to his bedroom. It was summer in Texas so we slept in just our underwear and no covers. About 45 minutes after going to bed.. is was a double so we were pretty close.. I felt his hand brush my bare thigh. I figured he was just rolling over and wasn't used to sharing the bed with anyone. I did freeze anyway just so I would not wake him if he was just rolling in his sleep. Then I felt his hand slide down my thigh... now I really froze. I was scared now that he wanted to touch me. I had an earlier experience when about 10 with an older neighborhood boy so I was spooked.

I was scared.. and curious at the same time. I was nervous but also wanted to see how far he would go. I had not even been with a girl yet other than kissing so this was all new. Over the next few minutes his warm hand slowly moved all over my left thigh and finally up to my waist. I felt his fingers slips under the waistband of my undies. I had to force myself NOT to raise my hips to help him pull my underwear down. He slowly worked them down until they hung on my hardening cock. I was sure that was a dead giveaway that I was not asleep but he pulled the material up and over my hardon so he could pull them down near my knees.

I didn't know what to do. I knew I would do something that would tell him I was awake and I was not ready for that conversation. All I could think of was to act lick I was dreaming od being with my girlfriend.. so I started to mumble her name in a sleep way. Either he was not convinced and didn't care or didn't care, he just continued running his fingers all around my cock. Then I felt him lean over and his warm breath on my belly. I nearly freaked. I assumed he was just going to play with my cock, maybe jack me a bit .. but now I knew he was going to suck my cock.

His warm lips almost made he spurt right into his mouth immediately. I had to think about the smell and dust of resurfacing my surfboard to keep from cumming. His mouth felt soooooo fucking good. I had never imagined it would feel like that. I just laid there and let him suck my cock off and shoot a huge load of hot, gooey cock cream into his mouth. He took every drop, then sucked my cockhead very gently until he had every bit. Then he slowly worked my underwear back up my hips. All this time I was moaning my girlfriends name and hoped that any involuntary bucking of my hips was attributed to my "dream".

I thought he was done but he took my hand and wrapped it around his throbbing cock and proceeded to jack himself off with my hand. Again, I nearly freaked but it was so exciting.. and I was jacking off another guys cock.. even if involuntarily! I breathed a long sigh of relief as I felt him finally roll over. My biggest fear was that he would want to mount me and slide his cock into my virgin ass. Three months later, after several more sleepovers, I was naked, on my knees with my ass up, taking his cock deep into my boi pussy. I had finally confessed to having not been asleep before. He said he knew all along LOL Now I wish I had reciprocated and sucked his cock all those years ago. My loss.

This is a followup to post #4 and #6. I am now a fully certified cocksucker!! I have sucked many cocks, and swallowed a lot of cum, Every one has been different, and was great. Now I am getting repeats, and developing a sexual relationship, can't be beat. If I had followed my desires instead of my fears, I could have had many wonderful years of gay sex. For me, this has been a rewarding journey!

By chance, when I was fifteen, I discovered that people were going into the men's bathroom at the train station near my house and taking a long time, which made me very curious. One night, I plucked up my courage and went in. I found men having sex; I'd never seen a porn movie before. So, it was my first time seeing people having sex. I stayed there for a while, but I didn't have the confidence to stay there. I left the station and sat on a bench watching people coming out of the bathroom, and that's how the hour passed. Later, a man sat next to me. After a few minutes, he started talking to me, but I didn't pay much attention to it. At one point, he asked me a question, and I looked at his face, and he was very handsome. And then we started talking. After half an hour of talking, he invited me to his house, which was very close to where we were. I think I was completely unconscious at that moment. I was fifteen, and he estimated I was thirty-eight. We went to his house and then to his room. There we chatted, sitting on the bed, and I was honestly shaking with excitement. I'd never had anything with a man before. That night was incredible because he was so kind and sweet to me. I remember him getting naked and having an incredible body, and he laughed because I was touching him all over because it was the first time he had a naked body for me. We spent the whole night naked, kissing, and finally we masturbated together. Now I'm his age, and I'll keep that memory in my heart forever.

I had two first times - one a boy, and the other a man.

When I was in 6th grade I got a call from Jeff to come over. He and two other boys were naked and his parents gone. They were playing and wanted me to join them. Heck yeah! We all had talked about our bodies and how good our little dicks felt when we played with them. I got naked too and be touched each other and explored our bodies. We were all hairless and inexperienced but loving the feelings of being naked. I remember being attracted to assholes - we rubbed each other but that was it that time.

We continued to meet when Jeff's mother went to work (she was a nurse). His father was away in the Army. We started using baby oil to enhance the slipperiness of our hairless bodies, and found that it make anal play more fun. We used pencils first then other household things to penetrate each other. Though we played with our cocks and got stiffies, penetration was impossible.

Then Kinsley, the older brother of one of the other boys joined us. He was in 9th grade and had hair on his much larger penis. We all wanted to know what it felt like. He showed us how he masterbated. It was amazing to see his cock hard. He must have been horny when he got naked with us. He masterbated and came just a little cum, but it was amazing! It was a new world we were anxious to join - but we could only get our stiffies hard but no orgasm.

I don't remember using our mouths on each other - just our hands with the baby oil. The next time Kinsley joined us, he was already bigger - body and cock. I was totally taked by his body and cock with it's bigger balls. He said the he wanted to put his dick in one of our holes to see what it felt like. Jeff took him in his mouth and sucked on him, but didn't want him to use his ass. I, on the other hand, enjoyed whenever my ass was rubbed or penetreate by fingers or objects. I told him I would let him use my hole. He got some vaseline and rubbed it on and in my ass with his finger going deep in me. I remember the sensations to this day! Then he had me lay down on my stomach and pull by bus apart for him. I pushed his head into me slowly It hurt for a minute that felt wonderful! He had read the sex questions of Playboy about how to fuck a girl, and used those things on me - lube, slow at first, then adjust to the girl. I was the girl! He went deeper into me (it was not a good position for him, but it actually worked for me so he didn't go too deep!) He almost moaned as he pushed deeper into me, then couldn't hold back and went in and out, faster and faster. He quickly cumed in me - my first fuck, and it turns out, his too. I was hooked - I was his as often as we were available - not just when the boys were together!

He got very skillful and could stay hard for a long time when he wanted to. He made more cum as he got older. I learned to take an enema (from a rubber bulb syringe) to be clean for him. I became his buddy and we hung out, and when ever it wan't too likely to be caught, he fucked me. I never had the interest to fuck a boy, but him to fuck me. Later, other boys of our group were able to get hard and cum. They all liked that I loved to be the girl so they didn't have to recognize we were all homosexuals! Our secrets stayed in the group, and out parents never found out. When I grew and could hold an erection and cum, I loved to be with girls. My first girl was when I was 16 - I love the feelings, as did she. I never had my cock in a boy or man, but loved to enjoy men. Funny, I am only romantic with women.

When I went into the Army I didn't have man sex. I was married and never played around. When I was in business, I got the urge for man sex again - i knew most every gay bath in the cities I traveled to. My wife never knew for sure I like me to use my hole, but I think she suspected. I always played safe. My double life has never caused an issue.

After my wife passed away, I took steps to become more a a girl, but that is another story!

My second first time (with a real man who knew what he was doing with his big cock - that's another story!

On a typical weekend night several years ago, I had two cute girls, a brunette (Renee) and a redhead (Heidi) who were kind of "with" me. We'd met this good looking fit, emo-ish guy at the bar (I'll call him Tom) who was pretty fun to hang out with. Skip forward a few weekends, and after beers at our bar he invited us to his place. We were walking to the bedroom and talking when he just started making out with me. I was pretty buzzed and went along with it. We stood there making out while the girls went to the bedroom, and he started rubbing my cock as we stood there. I was hard instantly and he kept rubbing it... Which was a completely unusual experience for me, but it felt good... So we went to the bedroom and made out with the girls for a while before he pulled my cock out and started masturbating me in front of them. The brunette took our Tom's cock out and started sucking him while he masturbated me, then the Heidi disrobed from the waist down, and pulled him into her. They had sex while I made out with the brunette, eventually moving to the floor with her and fucking her from behind while they fucked on the bed. We eventually had to break to use the restroom (and drink just a little more) - The girls went first, so he started making out with me again. I joined him back on the bed where he masturbated me until they came back. After we'd all relieved ourselves, we switched girls and alternated between fucking and masturbating them. He came with Heidi, and Renee and I made out until the alcohol and late hour put us to sleep. The four of us had a pretty good time that year. I started to date Renee regularly. One night, on my birthday we all went out, then went to her place. Heidi fell asleep early, so Tom and I took turns fucking Renee while we toyed with her nipples. It ended with me on the bottom, Renee in the middle and Tom on top behind her. We DP'd her until Tom came. Feeling his warm cum burst all over my cock made me cum pretty quickly. We all laid on the bed, satisfied, and fell asleep. We woke up the next day and milled around and talked. Heidi left early... then Renee got on top of Tom and started making out with him. They went right back to it, with her on top, giving me a nice view. They fucked, off and on from morning until night, which I was a little too tired to participate in this time, so I just took naps between watching random stuff on TV. When it got dark I took Renee home, and we slept the weekend off. Those were pretty exciting times. Tom and I never really had "sex," but we had a lot of fun.

Very erotic, very nice, very loving

Awkward, but damn good 😃

Was 27, met a married guy (about 35-40) on dating site, who wanted to try it with a man (oral only - said he is not ready for something more. I was either, though). He met me in a hotel room, and after quick shower, present me his average-sized cock. It was my first time sucking (I didn't even try on something inanimate before), so it was sloppy, inexperienced, and very awkward, but guy seemed to like it 😃 And I definitely did 😄

First time anal was about a month after, with other guy, 45 y.o. We met in his home, and after some talking went to a business. It was painful, but since I was masochist, it worked worked for me as well. Just after the sex (we were fucking under the blanket, because of very low temperature), I found out, that he was relatively thin, but impressive 21 cm long, that probably cause such pain. Still, had a sex with him few more times, until he had to move to other apartment too far away

I was around 10 or 11 when I met Clint (not his real name). His parents had a seasonal vacation home not too far from where I lived. He was several years older than me, but we fast became friends spending much time together at the beach, camping out, and talking about everything and anything. As one would guess, some of our conversations were about girls and sex. Clint, who spent his winters at a boys boarding school, seemed far more worldly than myself and our conversations would sometimes focus on activities such as masturbation and penetrative sex which, at this stage in my life, were mostly a mystery to me. My naive self absorbed every word! One day, several years into our friendship, we were playing what amounted to game of hide and seek in a rye field adjacent to his family's property. It was hot and we were running every which way though the 5 foot high grasses. I was the prey and when he located me, he burst though a wall of rye and tackled me to the ground. We lay side by side, panting and laughing. It was a wonderful moment. Once we caught our breath, the conversation led to girls (again) and Clint related a recent experience he had while attending at a dance social. He had met a girl at the dance and had gone outside to "make out". While telling the story, he rolled up on top of me to demonstrate their position and reenacted how he moved his hips while on top of the girl. With his body tightly pressed to mine, it didn't take long for me to realize that his (rather large) penis had become erect. I began to think that the demonstration may have continued for bit too long, but I said nothing as he had always been my mentor in such matters and, frankly, I was enjoying the lesson. It was not long after that thought when Clint's hip movements became considerably more pronounced and his breathing became rapid. Moments later, I heard a string of unintelligible murmurs, and a deep sigh. His motion stopped and I could feel the full weight of his now relaxed body bear down on me. We stayed in that position for a while with no words spoken. He finally rolled off and I could see the front of his shorts were soaked through. We didn't talk about what had just happened as I think we were both embarrassed. We parted for the day. Although we never again shared a similar experience, Clint and I remained good friends for a number of years after until he went off to college and his family sold the vacation home. We gradually lost touch, but I was left with an indelible memory of a most pleasant experience.

I was about 14 or15 when I met Jimmy, he was a year older than me. I'd never been with anyone or ever had anyone else ever touch me. We would jerk each other off. He soon asked me if I'd ever been fucked, I said no, but I loved thing in my ass mainly enema nozzles, so I agreed. We went to his room and undressed as I lay face down on his bed he went to his closet and brought out a jar of Vaseline and proceeded to lube me putting a finger in me. That felt so good as he finger fucked me. Eventually I could feel his dick trying to enter me. He pushed hard and he entered me( God did it HURT!) I begged him to take it out but he said the pain would go away( slightly raised my hips up on the bed and the pain stopped) It really began to feel good and I was hooked. He would cum in me and it was wonderful. We would reverse roles but I preferred being the bottom. He would have me put on his sisters clothes from the hamper, so I began to feel like a girl. This continued until he graduated from High school. I miss those days!