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.