Your First Time Having Sex

I was 19 (or 18, not sure anymore) years old when I had my first intercourse. But I used to play with my girlfriend long before.

I have been two years together with her. We did some petting long before. She was scared of Penises and did not like to touch or give me oral sex. As the initiative came from me all the time, I gave her Oral. I also used to Rim her nice Butthole long before any intercourse.

At some point I tried to insert my Finger. She liked it a lot. From there on I used my fingers to penetrate her for some months. Later I tried the same on her Butthole and with both holes with my fingers and tongue. I always liked how when she got in the mood she pressed her body against my face or fingers to fuck herself with it. But she seldom moaned or said a word while doing it.

Well, sometimes she gave me subtle hints, that she wants me to do her with fingers and my tounge. Like she would wear a skirt with no panties or stuff like that. But never directly told me that by any words. Maybe she needed that mysterious atmosphere.

All this time I used to do it to myself, as she wanted not to help me finish off, as she was to afraid of my dick somehow. Well, I respected that. Still got to play with her, this was enough for me for a long time 😃

After I was two years together with her, I thought its time to try the real sex. As she never took initiative or gave any sign that she wanted this and I was too shy to try it before, it took a long time to this point.

It was in missionary position.

First I did warm her up with some oral sex and fingering. Then I used a condom and slowly inserted it into her wet pussy. It felt so warm. I could feel the inner structure with my penis. I was scared to hurt her, as I have heard a lot of women do not like the first time.

Due my experience with petting and oral sex, I was well aware of her clitoris. During all the penetration with my dick, I used to stimulate her clitoris with my fingers to give her a good and relaxing first time.

I was excited as hell. It took my only a few minutes to come.

It removed myself from her vagina, but she began to moan and telling me to go on. Well, I was finished but still in the mood. So I penetrated her with my fingers and my mouth again. After 5 minutes I was ready again. Changed Condom and went on again. This time it took me longer to come.

With my penetration and my clit rubbing i managed to get her an orgasm. Oh man, those contractions with my penis inside her, I will never forget that.

After our first time she opened up her mind. She was more open to talk about sex and we had it many many times. We even tried anal sex. But only a few times.

As time went on, we broke up eventually. But this memory will always be present in my head.

My girlfriend and I were 15. We had played with each other forever and one day we decided it was time. We were both virgins. I barely knew how to get a condom on, and I was so excited I almost didnt make it to that point, but I settled down and got to it. I asked, "Are you ready?" She said yes and I proceeded. So it was awkward as hell. It lasted about 10 minutes. I had to thrust softly so my parents would not hear us. Obviously it felt so good I became hooked instantly lol. She was satisfied and we both came. Sadly we didnt stay together. We still talk every once in awhile and keep up with each others lives. It felt good and awkward because neither of us had a clue what we were doing, but it opened the doors for me and I ran wild!

I won’t say I didn’t enjoy it. It was exciting to get naked under the covers and make out with my friend. The actual sex was clumsy and over with too quickly. The learning curve was a great experience.

My first time was great and was with my girlfriend who eventually became my wife. My car would not start after work during an extremely cold winter day. She saw my dilemma and offered to pick me up at the repair shop. Then she said why don't you come in and warm up. After a warm bath, she washed my back and then led me into her bedroom. I proceeded to undress her as I could see she was highly aroused. She apologized for her small breasts which by now had grown puffy nipples which looked awesome to me! I was on my back as she mounted me and

We proceeded to enjoy the moment!

My first time having sex was with my best friend in high school. I had had a crush on him for years. I had known him since preschool. Our moms had baby sat each other and I had seen him naked many times. What intrigued me about him was when i first saw his cock. It never dawned on me that there might be differences between his black cock and mine. I learned that not everyone has their foreskin removed. The first time we did it he gave me an enema first. After I finished expelling I lay on my back with my legs spread. It hurt at first, but he went slow. It felt so good when he came in me.

I enjoyed my first time but I'll bet she didn't. It was my friends sister and I didn't do much foreplay and she wasn't wet enough. It also took about 2 minutes. I was a quick learner though but I was a lousy piece of ass my first time.

Same here. I would be so embarrassed about that now. I hate to think about it.

Girls are often better off having an older man first time. Most know the anatomy better and last a little longer then a virginal teen boy.

That is my advice for a good first time.

And in an ideal world all the virgin boys should have an experienced girl to teach them.

And in an ideal world all the virgin boys should have an experienced girl to teach them.

It should be an experienced woman, not a girl. That's how it was for me, and indeed it was ideal.

It should be an experienced woman, not a girl. That's how it was for me, and indeed it was ideal.

Braggart! We all couldn't be so lucky. Why is it the younger girls don't want an older guy to show them the ropes?

My first was one of my sister Lisa's high school friends. Her name was Jill, and it happened one afternoon in summer. I was 14, and Jill was Lisa's age, 18. She had dropped by to visit Lisa, I was the only one home. She asked if she could come in, and because she was really cute, I readily agreed. Mom was out for the day, and all three sisters were not due home for several hours. We talked about school and songs we liked. After maybe fifteen minutes of small talk, Jill hit me with a bombshell! "I really came to see you! I know Lisa won't be home until later." I was very (pleasantly) surprised, and stammered, "Why?" She blushed, and answered, "Lisa and I know that we both get enemas at home, and she told me you do, too. She also said that she sometimes gives them to you." It was my turn to blush! Here was an "older woman" telling me she knew about my enemas! I told her that was true, and asked why she said anything. If her first admission was a bombshell, her answer was the atomic bomb! "I think you're cute, and Lisa says your peter gets really big when she gives you an enema. I want to give you one and see what happens."

This was beyond my craziest fantasies, and I asked her if she had ever given an enema before. She said she gave them to herself. I asked her if I had to take my clothes off, and she said, "Of course, silly! How can I put it in you with your clothes on?" I said, "ALL of them?" She said yes. I said, "I don't know, I've never been naked before except for Mom and Lisa." She hit me again with, "I'll take mine off, too, so we'll both be naked." I repeated, um...I don't know..." She then clinched the deal with, "I'll let you give me one after you take yours!"

We went to the bathroom and mixed up my 2 qt SSE. Then, Jill undressed me, and touched my erection, which appeared without the aid of soapy water. She quickly undressed, took my hand, and led me to my bedroom. I dumbly said, "I thought you want to give me an enema." She said, " I DO, but I really want you to screw me. Then, we will do the enemas!"

That was my first time...but not my last with Jill. The enemas were fun, too. Oh, years later, Jill confided that she and Lisa set upthat first meeting.

Braggart! We all couldn't be so lucky. Why is it the younger girls don't want an older guy to show them the ropes?

Well... I'm not so sure it's always actually true that they don't (thinking of one girl in particular who actually stalked me for 2 years or so). 😁

Perhaps I've just been in the right place at the right time occasionally.

Braggart! We all couldn't be so lucky. Why is it the younger girls don't want an older guy to show them the ropes?

Well I didn't want a VERYold guy but I was happy to have an older male be my first. He knew how to get me nice and wet to the point I was craving his cock to just get in me. He was a few years older than me, more mature them some tumbling teen spending more time getting my bra off then having his cock in me.

Well... I'm not so sure it's always actually true that they don't (thinking of one girl in particular who actually stalked me for 2 years or so). 😁

Perhaps I've just been in the right place at the right time occasionally.

I did not stalk you. I did a lot of watching though because I meant to get you. lol 🌹 🌹 🌹

Actually I was somewhat tongue in cheek. My late partner was actually 11 years younger than I was so I got lucky I guess.!

... and so did she

Well... I'm not so sure it's always actually true that they don't (thinking of one girl in particular who actually stalked me for 2 years or so). 😁

Perhaps I've just been in the right place at the right time occasionally.

@DrZ you were not stalked, you were chosen. 🌹 And really you never stood a chance. 😉

@DrZ you were not stalked, you were chosen. 🌹 And really you never stood a chance. 😉

I had just made my mind up and I did not let him get away. 😜 🌹

Well, my first time, at 15, was with a 32 yr old neighbor and I fucked her in doggy, missionary, cowgirl and reverse, bent over, piledriver and even upside down! She had at least 10-12 orgasms before I filled her with 2 gallons of cum that she begged for, half in her pussy and half in her mouth! Then she told me I ruined her for any other man, and we had sex 10 more times that night!

Oh, wait.. no, that was the Letters to Penthouse version..

My first time was not quite my best. I was 19 and home from college for the summer. I had gotten to 3rd base with a previous girlfriend but was now dating someone else, who wasn’t a virgin with one previous partner. I was supposed to be saying good night to her since it was after 11 and my parents went to bed in our small single story home. We managed to be making out on the couch trying to stay quiet so my parents wouldn’t hear us. We got really hot and heavy and she was kind of on her side, leaning on the arm of the couch. We pulled her pants down JUST below her butt, just in case we had to quickly jump up and dress if a door opened! I got myself out of my shorts and she was so wet that I slid inside her easily (HOLY FUCK THAT FEELS SO GOOD!!), then I slid out, and came on her ass cheeks. LOL

Not exactly much action going on there! I cant say for sure if I made her cum that night with my fingers, but we certainly did lots of that and oral and other much longer sex for the rest of that summer. Not the greatest story/experience... but thats the answer to the question!

And in an ideal world all the virgin boys should have an experienced girl to teach them.

Back in time - let's say pre WWII/WWI Europe during the belle Epoque and before, it was not considered all that unusual for a family member (a father perhaps or an errant uncle) to take a virgin youngster to a brothel for an initial initiation. All very practical with no emotional issues.

That was the ideal word - but too bad so much else was wrong in the world in that time period though ... ha ha

And in an ideal world all the virgin boys should have an experienced girl to teach them.

. . . it was not considered all that unusual for a family member (a father perhaps or an errant uncle) to take a virgin youngster to a brothel for an initial initiation. All very practical with no emotional issues.

@agracier, @roscoe Sorry, I really disagree with this. I would NEVER have wanted this and would have HATED the experience! First, yes, boys/men may ‘suck’ at first time sex (myself obviously included), but so what? Virgin girls are no better either!! Should they all find an older more experienced man to fuck the first time? Why does it matter for the boy and not the girl? Mutual pleasure and fun can happen even if the male is awkward or comes too fast.

Being awkward or unsure is just part of the experience, part of learning. If you are with someone you like, then they won’t care, even if they had previous experience. If they DO care and make fun of you or whatever, then you obviously picked the wrong person to have sex with. Oops, lesson learned.

Second, I just abhor the idea of paying someone to be with me. No matter how nice and comforting or how well they teach (in this virgin/prostitute scenario) they are there, with you, for the money. Everything they do is fake and suspect. Why would I want to fuck someone who doesnt want to fuck me without money exchanging hands? Its not about being all emotional ( I certainly dont have to be in love to have enjoyable sex, although I do have to like the person ), its just that my desire for them comes in part from their desire for me. My pleasure in having sex comes from their pleasure from what I do to them. Once a party is being PAID to be there, all of that is lost.. no matter how many screaming orgasms she has, real or otherwise.

So nope, no matter how ‘bad’ a virgin male is their first time, thats just part of life.

@agracier, @roscoe Sorry, I really disagree with this. I would NEVER have wanted this and would have HATED the experience!

Sure, you can hate and abhor the idea, but that doesn't make the custom any less true. And naturally not every family would have thought it acceptable either.

For instance with proletarian/working class youngsters, there would have been little need for any formalized initiation. Sexual experiences occurred at an early age in the main and as long as no pregnancy occurred, little was thought of them. This pattern of sexual licentiousness of the working classes in the past, was by the way one of the (many) reasons they were looked down (despised perhaps) on by their 'betters' of the middle and higher classes.

Then there would also have been religious families, those that more or less practised what was preached and would never have partaken in such a way of initiating a boy into sex. But then again, there would have been many formally religious families that would still have thought it a practical method.

And there were undoubtedly many a youngster in the past who indeed ended up hating the experience. Either through a homosexual inclination for instance or because of shyness or feeling awkward or fear of contracting a 'social disease' or whatever. And there were certainly those who believed in the notion of romantic love in its purest form, with exclusivity and all that.

But whatever you may think personally, in a particular historical cultural context, it was considered normal, something accepted.

Not sure that this topic isn't here because I do know that I have written about my first time, losing my virginity, on this site more than once. That said, this was my first time experience.

It was the summer of 1971, August to be exact. I had met a group of kids the year before at the beach and couldn't wait to hang around with them this summer. Summer of 71 was also the year that I got my period for the first time.

One of the boys was a little more worldly than the rest of us at that time as far as sex goes, lucky for me. Weeks before we had made arrangements to have sex one night.... the anticipation almost killed me. But when I arrived at his house he asked me if I wanted a drink...alcohol....then took me upstairs into his bedroom. The window was open wide, white diaphonous curtains gently blowing in the ocean breeze. Clean white sheets on the brass bed. He had placed a dark pinkish scarf over the table lamp to dim the lights.

It was all very romantic for a 14 and a half year old girl. I was shaking all over. Ready to taste the forbidden fruit. My legs, my core just shook.

Looking back, I know he really just wanted to have sex with me. Period, but unlike other boys our age he was surprisingly gentle and loving. Tender and quailed my fears. He knew I was scared and nervous and shaking but we finally did the deed.

I am sure I had zero orgasms but having sex with a boy was so forbidden so naughty it was heady enough. I believe we did it two maybe three times. I don't remember the pain I was too nervous. It was exciting. Sexy and super pleasurable.

It was a kind loving experience I remember to this day.

I was raised in a very strict home. I started masturbating about age 13. I never dated much and never ever touched a female sexually until I was age 24 or 25. I was raised that it was wrong outside of marriage.

My first sex was with a Korean woman about my age. For some reason Asian Women really turned me on. I had been to a party and had fun dancing and chatting. I think she knew I was inexperienced and so she moved slowly teaching me how to treat a lady. I am not sure that had even seen a female naked my sex education had been a birds and bees conversation with my dad. And what little I was taught in school.

I dated her for a year and most of the time we had sex and she taught me how to please a female. Eventually I moved and that was the end of sex training. Looking back I realized after reading that she was a dominant.

College dorm room of my girlfriend sophomore year. Thank you, my dear. Very warm and lovely in your bed.

Her apartment, very close quarters. Came & went just like that.

Mine was on a barn when a few of us had gone away camping.

Everyone in the group knew some people, but nobody knew them all. I was getting on really well with one of the group who was new to me, and we started touching each other more and more, up the thigh etc, as we were sitting around the campfire. I kind of saw where it was going and felt ready to have sex.

We went of to the barn, where nobody was around, and literally rolled in the hay. He had a bit of experience and knew what he was doing.

I wouldn’t say it was the greatest sex I’ve had in my life but it didn’t hurt and I enjoyed it.

Not having expected to have sex, I wonder how many girls in the group got pregnant that night due to a lack of preparedness with contraceptives.

It was a group of mixed ages, and I’d imagine a mixture of experiences and expectations when it came to sex. There were definitely condoms there and they were used.