First time with a partner ... how did it go?

Back in the day I partied pretty hard. It was The summer of my senior year or the summer after. There was a group of us working a festival for the Fourth of July and building a float for the parade. It was sort of a small town Mini Woodstock thing going on. It was hot and we all were drinking and partying pretty heavy all day long and all night long. Sleeping arrangements were add Hock at best. I woke up the next morning in a sleeping bag no idea how I got there - and to an empty bottle of Jack along with an empty bottle of gin. Pretty certain there was a blank sheet of acid floating around. The surprising part was there was a girl in the sleeping bag with me and we were both partly nude. We both woke up looked at each other looked under the sleeping bag, Gathered our clothes, got dressed and part ways. Odd situation may even odder. I'll never really knowing what happened.

Another situation was I was at a friend of mine's bachelor party. It was a bachelor party that movies are made out of. Girls, dancers, music, drinking and doing other substances - you name it it was going on. By the end of the night it was like a mass orgy happening. I hooked up with a chick and she was giving me Skull. It took a while but eventually blew my load into her mouth. It was my first blow job. Shortly after that the cops broke into the hall started breaking up the bachelor party and things got out of hand. Was kind of a mess. A bunch of us got out without being arrested or any other issues and ended up taking the party to one of my buddies apartments. The girl that I had hooked up with came back with us and she was all me looking for more. She seemed duly impressed with how long I lasted when she was blowing me. But honestly it probably had more to do with my condition than my actual staying power. I was just so absolutely wasted that there was nothing I was going to be able to do for her (or me) in that state. I was fried.

So there you have it. I'm guessing my first couple times (more) I was so mentally impaired that it was ridiculous.

For the record, I have cleaned up my act immensely and truthfully, sex has become more enjoyable - and far more ... rememberable.

 

I always believed sex, and life in general, is better when you remember what happened, having a memory of it.
Ok some moments are best forgotten LOL

My first was with my first GF, we had played around a fair amount until then, like fingering, groping and feeling each other a lot, stroking.

We went out of town and rented a hotel room, she was a virgin so I took the lead the entire time.
Condom, check
Lube, check it was actually spermicide. We were a bit paranoid about getting an unwanted pregnancy.
Ready.
I went easy after some foreplay, pushed in bit by bit until completely in and stayed there until she felt somewhat “used” to have it in.
Then it started, the condom helped me last longer that time and I managed to last kind of long enough to do it right; tear her hymen, enjoy some sex before orgasming.

We were caught up in having done the deed so there was no follow up with me doing more for her.

Sadly that became the way of doing things together although I usually gave her one orgasm after I had mine, once we got a bit more experienced. That was because it took her a while to reach orgasm and I always assumed that was it for her.

 

However it was not my true first time, as mentioned in other threads I had a few prostitutes before, I was too awkward to cross the line to get real close to girls (and it was never the opportunities that lacked).
The semblance of sex I had experienced was nothing more than letting the prostitute be on top and make my cock feel good while I played with their breasts.

 

My first time was kind of a bumble fuck. She insisted on using a condom. It was too small. I couldn't find the entrance to her pussy. With her help I finally got inside but I didn't feel anything. After a long time of me pounding away she pushed me off asking what was wrong. When I revealed that I wasn't feeling anything she made sure the condom and I parted ways. My second time with a new partner was in a brothel in Nevada. She took over and it was a great experience. Both women knew what to do which helped a lot. Number 3 and subsequent times have all been great as I had learned how to fuck by then. I also learned what size and kind of condom to use. So now every time with a new partner it goes pretty good. There's always something different which is what I like about it.

 

My first time was on our wedding night. We had been dating almost eight years, but I loved her too much to risk getting her pregnant, so I waited. She had experience with other guys, so it wasn't the first time for her, which was good. She was able to help me get over "first time anxiety" and enjoy the experience. The second time, a few minutes later, was even better. By the time we got out of bed the next morning, we had done it seven times, and I was an old pro, thanks to her loving patience.

 

As Barry said, my first was a bumble fuck! Two 19 year old virgins who had dated a year. We initially set many boundaries that were eventually broken. Lots of oral sex but we weren't going to do the deed! One night she just said "put it in"! It hurt her quite a bit, and even with a condom I came quickly. Yeah, I felt good physically, but emotionally felt bad from her pain. We broke up a year later. I'd like to go back today and give her a first class screwing

First time with my wife was awesome. We were both so horned up from all of the flirting we knew where we were going. She's on the pill, no condoms needed. She came twice, and then the third time when I came in her. Lots of afterglow making out, and then round two! BEST sex of my life! I'd love to go back and relive that night again, over and over.

 

first time ever was a "bumble fuck" as earlier posters have said.
But like the Bob Seger song - Night Moves, we were working on our night moves... so we kept bumbling till we learned a thing or two dozen.
First time with "a partner" I am assuming this refers to the first time I was with the woman who became my wife. That went very well, we were both experienced and it was a foursome.
My FWB knew my future wife who was also with a FWB.
We hit it off and began dating... it really takes the pressure off when you know you are getting lucky.

 

I’ll use Mrs TC as my example, we had known each other for a little bit we decided to go on a date for dinner & drinks to get to know each other, thing worked out well so we decided to go out again.

That next week we meet at a bar for some drinks with friends, that evening we decide to go back to her place. She asked to give her about 10 minutes then come over. About 5 minutes into waiting some more friends come in and they buy me a couple of drinks then a couple more. I’m late, very late I finally get to her place she is not very happy nor very receptive to my advances. We finally get to bed, I have had to much to drink, I’m clumsy everything is just going completely wrong. “ I just want you to finish “ is what she ended up telling me, that was my invitation to leave.

I definitely was not going to call her again, not after that disaster, she didn’t call me either.

A few weeks later we bump into each other again at the same bar, we got to talking again, this time we go home together, the second time was the charm, we have been together ever since.

 

I forgot about penetration on the first time, just concentrated on the girl and getting her off. Gave her a good orgasm (she screamed quite a lot) just by rubbing her pussy and gently tugging on her clitoris. Made sure she felt good and got her off about four or five times before she wanted to be penetrated. Worked out quite well, she was -crazy- for more sex after her effective introduction (she was a virgin) turned out for her to be so unbearably pleasurable. She was quite negatively disposed at the start, for some reason had the idea it had to hurt - after I showed her it need not hurt at all she was much more relaxed and -very- eager to be penetrated.

 

My first time in a sexual act was with a street girl. Paid her. Followed her to a room near the old Boston Combat Zone. She washed my dick, took my clothes off and had me lay down with my head propped up on a pillow. She stripped (oly wearing pants and a button down shirt) and lay down beside me. I had taken a condom out of my wallet and it was next to me. I was nervous. Now I had watched enough porn in the movie theatre around that district to know what I wanted. I wanted to touch her boobs, touch her pussy, have her kiss my penis and I wanted to put it in and lose my virginity. She settled in close to me and I reached over to feel her breasts and nipples and I got hopelessly hard. She bent over and took me in her mouth and I couldn't believe how warm and wet that felt. Then she swirled her tongue once or twice and sucked up and down a few times before pulling off. I started to ask her to wait as she stroked me and then she put it deep in her mouth again and I just let go. Couldn't hold back. It surprised her and I felt terrible. Even though I had seen girls in the movies take it in the mouth, I didnt think that it was "normal". I thought it was reserved for porn. I couldn't get it back up again and ended up dressing and leaving. I barely touched her between her legs and definitely not inside her pussy. So, I left a virgin and I'm still kind of embarrassed that I lasted about 30 seconds before shooting. I didn't even get to ask if it was OK if I did that (something I always do now when it's the first time). I really wanted her to slow down but even if she did, I still think I wouldn't have made it to regular sex. So, it went badly but felt good and it was memorable.

 

It was awkward and disappointing but I knew he had potential.

 

I'm glad she gave me another chance or some other guy would be enjoying her now.

 

To be fair and honest the first time together was somewhat of a train wreck but it wasn't terrible. She wasn't half as good as she'd built herself up to be over the phone the first two months before our first night together. We were both nervous and the venue was a motel and felt cheap . I'd drank too much from the long drive and being anxious so I wasn't anywhere near myself.

 

:-(..anxiousness can case this indeed! Lesson learned! ;-)

 

If I exclude the first sexual experience that was with a prostitute which was disappointing

First GF, we started with hands on for a while, she was a virgin, very naive and misinformed.
But love made those last two items not important, and I was patient anyway.
Handjobs were so good except the finish
Blowjobs were a bit of playing but they felt good
First time penetration was as expected.
I didn’t rush the when so it took months before we did it. She followed my lead and went along, the undressing, touching.
We were very careful with condom and her on the pill. The experience was nice because it was romantic, but tame, ordinary.
I was as gentle as possible going inside her gradually and giving her time to “adjust” before giving a little bit more until it was in all the way

 

We made up for it the second time we got together though. Both of us were like OMG!

 

I was a virgin till marriage. I played with the breasts and pussy of a couple girls (never the one I married) and one of those did a nice hj, but there was no penetration till marriage.

The gal I married was very prudish and very religious. It was obvious to me I would have to go slow. After a month of dating, I grabbed that gorgeous butt while we were kissing. I got a lecture about how she doesn’t believe in doing “stuff” before marriage. It was a stern serious talk. Before marriage, I never touched her butt, or her boobs or pussy. She did allow me to grind my thigh against her pussy while we kissed. (I’m not sure how she reconciled this with her prudish ideas. Many years later, she told me that as soon as our dates would end, she would finger herself to an orgasm.)
On our honeymoon, we had sex for the first time. She was on her period, but wanted to do it so we would “feel married”. It was awkward. I was shocked that while in missionary position that my virgin bride grabbed my dick and guided it into her vagina! I just couldn’t imagine a prudish virgin doing that. The sex was as unromantic and non erotic as you could imagine. A purely mechanical act that consummated a marriage. Afterwards, she felt nauseated. I felt cheated having waited for sex with her only for it to be so underwhelming. I’m sure the feeling was mutual.
Fortunately, the next time was far better and I got to see her orgasm for my first time.

 

She was 20, divorcee with 2 little boys. I was 20. Dated her a couple of times. Spent evenings in her unit. She dropped lots of hints about sex. She had an IUD in place. One evening as we sat on the couch she turned to me and opened her legs, knees up and beckoned me ontop of her. She unsnapped the fasteners on her bodysuit leggings thing. There was her hairy red vag, open and ready. I got my pants off fast, and got on and she sighed as my cock went in.She sighed and thrust her hips. I drove the cock in, loving the feeling. I lasted quite a while because I was nervous. Eventually I shot a huge load of come up her. I went on fucking her every evening for most of the year until we split over things. I wish I'd married her. My two wives have both turned cold after a few years.

 

:-(

 

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