Your First Time Having Sex

I was 18, she was 24 and very experienced. We made out on her couch and did it before we even got all our clothes off. I came pretty quickly but since I stayed hard, I continued until she'd had 3 orgasms. I rather enjoyed my 1st time.

I was a teenager, 15, at the time. This girl in my math class was super hot to me and she either volunteered at a doctor's office or worked there on weekends. Well she had a key and we snuck in after hours and did it on one of the exam tables. This probably explains my medical fetish.

I feel like a prude for posting this. My life is very vanilla at the moment which is why I’m here! ? My first sexual experience was actually very nice. I lost my virginity when I was 24, to my husband. The day had gone on just as perfectly as it could have. We made love for the first time in a luxury honeymoon suite. He seemed like he knew what he was doing but I honestly didn’t have any idea. I did quite a bit of learning, and it was painful but it was also fantastic! I love my husband so much, I just wish he wanted to be kinky at times where we weren’t just having sex! I’d love for him to want to play without having to be intimate every time, I find it boring.

The first time I was 21 and she was 18. We had talked about

Our if and decided to go for it. We went to a drug store and bought some condoms x and then drive to a deserted road we knew. We both undressed and got in the back seat. I was so excited and hard that I came before we did anything. I was so embarrassed. She said don't worry and since I was still hard she put a condom on me. She laid back and was already set so I slowly entered her missionary style. Since I had already came I was able to satisfy her prior to coming a second time. It was the first for both of us and it was great.

I was 18, she 17. We were at a drive-in movie theater. Did it in the back seat of my 67 GTO! It is something I will always remember. She and I were together for 6 years and I introduced my fetishes to her. More on that later....

I feel like a prude for posting this. My life is very vanilla at the moment which is why I’m here! ? My first sexual experience was actually very nice. I lost my virginity when I was 24, to my husband. The day had gone on just as perfectly as it could have. We made love for the first time in a luxury honeymoon suite. He seemed like he knew what he was doing but I honestly didn’t have any idea. I did quite a bit of learning, and it was painful but it was also fantastic! I love my husband so much, I just wish he wanted to be kinky at times where we weren’t just having sex! I’d love for him to want to play without having to be intimate every time, I find it boring.

You're not alone, that was pretty much me too. Though I'm not sure if my wife thought I knew what I was doing, I really didn't and was a bit afraid, even though I had read a bunch.

We were both 16. We have been married for 53 years now.

For me i was seventeen and three of my were heading back to college out of state about an eight hour drive from our home . About half way was a town that had a brothel on the outskirts , all being young we pushed ourselves to get courage to in . The girls came out lined up before us . Each picking who we wanted to go with . Fifty five years ago. I still remember her name was Cinnamon , nervously followed her back to her room . She said its your first time embarrassingly i said yes . Not knowing what was going to happen. She went into asking what i wanted and all i could think of was a half and half which my friends had talked about. Its a blow job and intercourse. After paying her the fee she stripped and helped me undressed telling me to feel her breasts while stroking my erect penis and checking me to see if i was healthy , then she washed me and squirted some liquid into my penis . Then knowing i was a virgin let me feel her all over . Laying me down she proceeded to lick my balls suck on me , seeing i was getting close she had me mount her as i became a member of the adult world . After completing she washed me off squirting the liquid into my penis i dressed and met my friends who were finishing also . We left for our drive back to school knowing this was going to be our rest stop from know on.

The first time was with a highschool girl friend. I was both horny and scared as hell to be faced with a pregnancy. The horniness won over and I found myself at a party in bed with her. I stripped down and mounted her like a champ but froze in my tracks. Every little movement took me to the edge and I wasn't about to take the chance. We kind of laid there for a while fully inserted and stone still. After an awkward few minutes I pulled out and got dressed. It felt great but I felt like an idiot. We broke up shortly after that. My second time was with a cougar and holy crap that was great. She was on the pill and I was in heaven.

The first time was awkward I felt clumsy. We were outside on a blanket. It was uncomfortable. I didn’t know what I was doing.

My first time was very strange. I had led a very sheltered life as anything to do with sex was a taboo subject with my parents. All I knew was the very basic things we had been told in lessons at school. Even more strange for me was the fact that I had no interest in sex. I didn't want to have sex with girls, I just wanted to be one. If anything, I wanted a man to desire me and make love to me. But I knew that I was not gay.? So I was completely confused.

When I met a friend my life changed. By sheer fate I met my friend, both of our secrets were exposed to each other at the same time. I was dressed as a woman and she was working the streets as a prostitute. We both confessed to each other what was happening, and once our initial shock and shame had elapsed, we sat down and talked to each other openly and honestly.

She was the only person I had ever been able to talk to, and to confide in. After about a month of visiting her house and talking honestly with each other, I left home, moved into her home and transitioned over night. I left all of my male clothes at my parents home, and with a mixture of the few female clothes I had secretly bought with pennies I had saved, and a few of my friends hand me downs, I finally started the long journey to become the person I should have been born as. My friend was struggling to bring up her own young children, having another mouth to feed made things even worse. I had to help, and pay my way. I had no money, no education and no job. My only choice was to follow Jenny into sex work. Not only was I trans, but I had absolutely no idea of anything to do with sex. She literally taught me everything over the next few days. She taught me what a woman wants, and also how to give a man what they want. With her training and careful teaching I went out with her and her friends to face the world.

I was 21 and my college boyfriend and I had talked about sex and I even went on the pill to prepare myself... like we were doing other things but never had full intercourse...

Anyways it was not very pleasant when it did happen. I kind of wanted it to be like a movie or TV show but instead two 21 year old virgins kind of fumbled around in my dorm room... and when he got it inside me it hurt so bad I started crying. I just remember telling him to hurry up and finish... anyways yes the sheets were bloody, and i felt sore down there for a few days. Sex got better after that but the first time wasn't fun.

My first time was pretty good. It was the summer I turned 22and shy, I was working at a restaurant and bar as a cook. One night I went in to relax in the bar and the manager as me to check IDs for bar entry, and was put on as bouncer. As the weeks passed, I got to know this group of girls and didn’t have to check their IDs anymore.

One Saturday night they came in with someone that looked as young as them. I carded her, and one of them said auntie got carded. And they laughed. Later on she came up to me and asked to dance, I told her she would have to clear it with the manager. She came back looking really sad and said he said no. I told her to go sit down and wait.

10 minutes later he took the cash register drawer down stairs to count out. I knew he be gone 20 minutes, I left my post and took her to the dance floor. She was a good slow dancer, really close and she put my hands on her ass. I was in over drive. We said goodbye and kissed as her nieces watched at closing time.

Jump to next Friday, her nieces came in and told me they were bringing Aunt Maria Saturday night for me. I couldn’t wait. The next night, they came in with auntie leading the way, dressed in a green dress with her boobs showing and a split in the side, pantyhose sparkling in the flashing bar lights. She kissed me and went to sit down and wait, her niece came back up to my post and whispered in my ear, auntie needs you to drive her back to our place when we’re done.

After a while the manager took the drawer downstairs and we hit the dance floor. As we were dancing a slow dance, her nieces left.

We closed down and climbed into my truck, I asked where to go, she coyly smiled and said to the park near by. We made out in my truck for a bit, and then she had to use the restroom. She asked me to hold her purse and went in, and came back out and asked me to open her purse and she stuffed her pantyhose in it. We walked over to a table and sat down and made out some more, she took my hand and put it in her dress to feel her boob. Few minutes later she pulled it out and put my hand between her legs and up to the promise land. She pulled out a boob and pulled my head to it. Her nipple was rock hard and pussy dripping. She unzipped my pants and pulled my hard cock out and played with it and said let’s go over to the grass in the dark. We walked with her boob out and dress slightly hiked up. When we were out of street sight she said let’s go and I asked her to be on top, she smiled and said ok. She pulled down my pants and I laid down, she unzipped her dress part way to pull both boobs out and pulled up her dress. I saw my first live pussy, she stepped over me and slowly lowered her self onto me. It felt wonderful and I tried not to cum but I did after a minute in paradise.

She leans down and said it’s alright and kept riding me. After she came and I shot again, we got up and walked back to my truck, she asked for a pen and paper to write her work number on and asked for mine.

We met up once or twice a week for the next 2 years when her work was slow, but I changed jobs and our meeting slowed down. I lost track of her, but if we ever found each other I would meet with her, and who knows maybe have meets again.

So I guess my first time was pretty good and she showed me what a woman wants

My college roommate boyfriend during a threesome.

Nervous as anyone else with opening-night jitters.

Came and gone just like that, but she & I had a long leisurely conversation afterward.

I was 16 when I had sex the first time. One of my girlfriends (not Susan) was my first and I had a great time despite not being experienced or more knowledgeable about how to manipulate the vulva for the most pleasure. Susan didn't lose her V-card with me either.

My girlfriend was not a virgin, but she wasn't an expert at sex either, but we both had a great time and I was thankful I stayed hard inside her for almost five minutes, which was a concern since when I was in a hurry at that age, I could "speed-cum" in 30 seconds if I wanted to. About a year later, Susan was the person who really taught me how to fuck and masturbate a woman. Many women after that benefitted from Susan's lessons!

Didn’t have intercourse til I was 18. It wasn’t bad but not real memorable either. High school sweetheart. It got better the more we did it.

A couple years of heavy petting and oral sex came first. First blowjob and first time eating her pussy are very memorable.

But our first oral sex actually was me licking her anus one night as she let me give her a supposed massage. One thing led to another, skirt up, panties down, and there’s her beautiful little white bare bottom. First time I’d ever seen it and no clue what to do so I caressed her for a while but wanted to know what she looked like in that very private place. I was only 16 and had seen enough nudie magazines to be very curious. I was a bit nervous but then gently spread her cheeks. She didn’t flinch. And wow there was her tender little asshole right there across my lap. Actually very appealing and not gross or anything, quite hairless, light pinkish, and totally clean. I could not resist so I very gently touched it and pulled it open slightly and then just leaned in and started kissing it. She just breathed deeply but didn’t move an inch. So I started licking. Not sure how long it lasted but eventually she turned and smiled at me and said she should probably go to bed.

Obviously I never forgot this First Time! It happened many times again, always her receiving. I didn’t get to be on the receiving end until some years later with a very willing girlfriend. But that’s another First Time story.

Traditional sex (penis in vagina) was at age 25 with my then to be first wife. Anal sex and masturbation was much earlier at age 12 - 13. Both were new experiences and very pleasurable!

@Romulus said

I was 16 when I had sex the first time. One of my girlfriends (not Susan) was my first and I had a great time despite not being experienced or more knowledgeable about how to manipulate the vulva for the most pleasure. Susan didn't lose her V-card with me either.

My girlfriend was not a virgin, but she wasn't an expert at sex either, but we both had a great time and I was thankful I stayed hard inside her for almost five minutes, which was a concern since when I was in a hurry at that age, I could "speed-cum" in 30 seconds if I wanted to. About a year later, Susan was the person who really taught me how to fuck and masturbate a woman. Many women after that benefitted from Susan's lessons!

YOU BASTARD. When I finally gave myself to you, you told me I was the only one!

Actually, we both know that even though you were not my first and I was not yours, I practically raped you at my parent's house when we were 17. I gained useful experience with other boys before you and I ever "did it." Your previous conquests did a pretty good job teaching you. I cannot deny that. You knew your way around the anatomy pretty well, you just needed a touch up on some moves, and I know a number of women benefitted from my giving you sex lessons, but I finally got you and you benefitted from my creative and disgustingly dirty mind.

I love you.

After reading all the posts from past to present it appears that many enjoyed the first go round.

After carefully reading susie's "sex" definition I now can clearly state that the first time my penis came in contact with a vagina at about 12.5 yrs does not qualify as sex as I was coitus interruptus by the young ladies mother arriving early from work at home and hence unable to complete the act. I will say from that point forward I could think of little else as so important a deed that must someday (soon) be accomplished.

But that was not my fate. Although I had a huge amount of sexually charged days sexual intercourse did not occur until I was 2 months shy of my 15th birthday. To that point I had experienced with my then present steady girlfriend "the everything but" with our favorite being the slide and glide of my penis in the spooning position along her slick pussy lips. I would cum fairly frequently together and digitally manipulate her clitoris. Finally one day while we were above the 2 car garage in a loft that held a bed she concented to the ultimate pleasure of allowing my eager penis to penetrate her vagina. We played for 2+ hours after school until her Dad arrived home from work. I could not wait for the next time we could "get away with it"

I know I loved to preform oral on her but do not remember any blood inspite of it being first for us both.

Well if oral sex counts

Me and three friends when we were all 15 went over to buy some pot. He was gone to get some more and his wife blew all three of us she was in her early thirties.

Oral sex (a blow job) is NOT "having sex."

What you describe is really mutual masturbation.

Oral sex (a blow job) is NOT "having sex."

What you describe is really mutual masturbation.

Reminds me of that famous (or is it infamous) saying "I did not have sex with that woman"...

Reminds me of that famous (or is it infamous) saying "I did not have sex with that woman"...

He was correct.

He was correct.

Yep - and that's when I learned that a BJ is not considered sex. Now if a BJ is not sex, then by the same token "anal sex" is not sex then?

YEP

And 2+2=5

Non-penetrative sexua; activity - "Outercourse" - also is not sex. It has lots of different interpretations, from petting with no actual genital touch, to oral, masturbation etc. Who the hell comes up with these terms?

https://en.wikipedia.org/wiki/Non-penetrative_sex

Non-penetrative sexua; activity - "Outercourse" - also is not sex. It has lots of different interpretations, from petting with no actual genital touch, to oral, masturbation etc. Who the hell comes up with these terms?

https://en.wikipedia.org/wiki/Non-penetrative_sex

Someone who got caught. 😉

I was 15+, she was 16; she had her parents station wagon. We parked at a turnout on the strand at Coronado, CA. It was quick, hey it was my first time. She was more experienced than I. We continued to date steadily thru High School. Then I went off to college and she didn't. We ended up splitting up and she got married. I still think of her as the one that got away.

Yep - and that's when I learned that a BJ is not considered sex. Now if a BJ is not sex, then by the same token "anal sex" is not sex then?

That's right. Butt fucking is not sex.

"Having sex" is a coupling of male and female sex organs---PIV.

A penis in the hand or clit in the hand or dick in the mouth or anus is NOT sex.

Is a Sybian having sex? No it is masturbation. Masturbation is not having sex either.

Other activities playing with the genitals are forms of masturbation.

I will acknowledge there are confounding bastardized definitions recently.