Your First Time With A Woman (18+)

[1049997]

How was your first time being intimate with an opposite sex (18+ of course)? Let us all know and vote in my poll and comment there too if you got a story to tell!

Your first time with a woman (18+): ultimate poll

 

[Derringer]

My first times were before that watershed but I can recall my earliest 18plus experience.
Despite my afforementioned hook ups I was still not a great swordsman. I have a tiny penis and very poor stamina.
The (un)lucky woman in my post teen era. It started off well enough until we actually were naked, I will not bore you with the forensic details as there really isnt much to tell.
Basically she was totally shocked and horrified when she saw how tiny my penis was and could not mask it. Although she appolgized for her overt reaction.
It did not totally kill the mood though ( which has happened a few times since with a number of other women. ) However after a much too hurried bit of foreplay I wiggled my little cock into her volumous pussy. It was definitely a bit lost in there and I only lasted as long as I did because of a lack of friction and the fact I kept slipping out. Even so I wriggled about for perhaps a minute or so before she asked me to stop. I volunteered to go down on her but she declined and gave me a dejected mercy wank.. ( about three or four tugs with a thumb and forefinger and I shot my load)
Because of the lateness of the hour and there being no night bus service along with insufficientbfunds

 

[18wheeler]

She made me wear 2 condoms. We we’re both virgins and she cried afterward. So…. Not good.

 

[deleted814719]

She made me wear 2 condoms. We we’re both virgins and she cried afterward. So…. Not good.

Oh, man. Crying after the act would certainly be a mood killer.

 

[18wheeler]

Oh, man. Crying after the act would certainly be a mood killer.

It was.
The whole situation was odd.
I’m not pushing when it comes to sex. Never have been. We were young and We dated a year before sex ever really came up. We messed around a lot but I never pushed sex. I did bring it up. Bht never pushed it. She wasn’t ready. Cool.
We actually broke up, her choice.
A few weeks later. She called me and apologized and said she wanted to date again. We talked and went out a few days later. While we were at dinner. She said she wanted to go home and have sex……. We did. And then she cried.
We had sex after than a lot and she never cried again.

 

[Talstar]

It had a happy ending then

 

[deleted136887]

Oh man, the euphoria afterwards!
And the anxiety before!
I was hooked for life.
I may have become a better lover , I may have picked up a few techniques, but women still surprise, and surprise and arouse me.

 

[12843051]

I lost my virginity quite late (19) and had told everyone that I had already fucked before. This led to me losing my virginity in a five way. One mate was fucking a girl next to me as my other mate was getting his dick sucked by the girl I was fucking

 

[Derringer]

My first times were before that watershed but I can recall my earliest 18plus experience.
Despite my afforementioned hook ups I was still not a great swordsman. I have a tiny penis and very poor stamina.
The (un)lucky woman in my post teen era. It started off well enough until we actually were naked, I will not bore you with the forensic details as there really isnt much to tell.
Basically she was totally shocked and horrified when she saw how tiny my penis was and could not mask it. Although she appolgized for her overt reaction.
It did not totally kill the mood though ( which has happened a few times since with a number of other women. ) However after a much too hurried bit of foreplay I wiggled my little cock into her volumous pussy. It was definitely a bit lost in there and I only lasted as long as I did because of a lack of friction and the fact I kept slipping out. Even so I wriggled about for perhaps a minute or so before she asked me to stop. I volunteered to go down on her but she declined and gave me a dejected mercy wank.. ( about three or four tugs with a thumb and forefinger and I shot my load)
Because of the lateness of the hour and there being no night bus service along with insufficientbfunds

I see I didnt fully conclude the original post - Because of late hour and no night bus service along with insuffientnt funds to afford a taxi. She stayed the night . We both had to suffer the morning after awkwardness. I assumed I would probably not cross paths with her again but about 2 weeks later she was at a house party I was invited to by some people I met at a bar. I saw her whispering to a couple of other girls and giggling while making a couple of glances in my direction. Couldnt be sure what she was gossiping about but I suspected it was about our embarrassingly disapointing hook up.

 

[Derringer]

She made me wear 2 condoms. We we’re both virgins and she cried afterward. So…. Not good.

I awoke to one of my one nightstands just staring at my pathetic little penis with a very distraught look on her face. ( we were quite drunk when we hooked up at a party or bar and at her insistance we went to my place to fuck) She had that look of horror one might have when you recall how you may have embarrased yourself the night before.

 

[davidc69]

a young prostitute, had to use a rubber

 

[verybored]

Both virgins. Obviously, it being the first time, struggled with the condom and had a semi by the time I got it on. Slid that limp thing in there and came embarrassingly fast. You could say it wasn’t exactly spectacular.

 

[davidc69]

nice cock !

 

[jtheimpaler]

First time was pre watershed… my 18th bday however I had a threesome… and yes.. it fucking rocked

 

[lapdog2001]

I didn't start dating until college and my first few girlfriends and dates didn't progress to sex. More often than not, I was 'friend-zoned' by so many women with whom I was interested in dating. Eventually I did form a very close platonic relationship with an attractive woman. We spent a lot of time together and some people thought we were actually a couple!

After about a year of friendship she crashed on my couch one night, and as I pulled a blanket over her I gave her a hug (which was normal for us) but also kissed her on the lips. There was no rejection, just a smile, so I kissed her again, and again, and then things really heated up quite quickly!

Caressing and fondling her breasts quickly changed course when she lifted her shirt and bra so I could suck on her breasts, and undid her pants and asked me to finger her, which I gladly did. My pants got unzipped and dropped at some point, and she started stroking my very hard cock. Since she was at the end of her period, we eventually stopped (after I got her off) and we snuggled up and went to sleep together.

The next morning, I of course woke up to a raging hard-on which she then took into her mouth, commenting on how huge I was. She then said 'If only" and I said "if only what?", and, "I do have condoms". She smiled, I grabbed a condom, put it on, and proceeded to have intercourse for the first time of many hundreds of times with her.

 

[Puffdaddy316]

Great post but and yeah the first time with a woman is really sexy

 

[lapdog2001]

That's so cool and hot! So you weren't her first, right?

No, despite her age, she was very well experienced. She'd had 3 serious long term boyfriends, but apparently fucked like a bunny when she was single, including hookups and one night stands. Her experience led to me learning a great deal about how please a woman in a very short time. She considered me to be one of her best lovers ever (her words) , and it had nothing to do with my penis size, although she thoroughly enjoyed that as well!

 

[Motion-of-the-Ocean]

As I answered in a similar thread, I can't go into details about the very first time for obvious reasons, other than to say that due to immaturity it was awkward and not very memorable. To say nothing of dodging a bullet by not continuing the relationship when we got older, considering how messed up her life became.

The next encounter with a different person when I was 18+ was not only better, but despite it technically being the "second time", I for all intents and purposes, consider it the first due to the vast differences not only in the sex, but the person who was special enough to eventually marry.

That time, from courting my future wife to eventually having sex was a slow burn over several months, but well worth the wait as her being older and more experienced than me, she taught me so much and rocked my world. There were so many milestone memories from first kiss to seeing her pussy for the first time, to eventually releasing an eager load into it.

That "first time" with her was significant enough to want to spend the rest of my life having sex with her and over thirty years later, the passion hasn't diminished. In fact, the biggest difference between the second "first time" and actual first time was in receiving oral as it was a new experience for me. It was early on I learned that unlike some relationships where there's less enthusiasm, my wife was into sucking cock from Day One and her enjoyment of that has never abated.

 

[deleted817718]

My first time I was 22 years old. I had been sex sully active with men for some time before then but not been with a woman, although I identified as bisexual. A female member of my group of friends that I knew but wasn’t very close to quizzed me about being bi one evening I revealed that I hadn’t actually been with a woman fully sexually, and she rather excitedly asked me back to her place. Before we started getting it on she was talking about us maybe hating a “friends with benefits” situation. To skip all the details of the act itself, afterwards she was asking me if I would be ok if we kept this between us and wasn’t very impressed with the sex we had just had. She did say it was clear I hadn’t been with a woman before lol

 

[mrbigdoc]

I was 18 and had noticed an attractive woman near our house in a resort area. I was staying at a friends house and the phone rang and it was a woman's voice asking for my friend. I told her he wasn't home at that time and could I give him a message. She said she needed a ride over to wait for him to return. I said I could come get her and bring her back to wait. I drove over and picked her up and I was so happy to see that she is the woman I seen earlier in the day around town.

We talked on our way home and she said she was 37. She was a knockout and as I the younger horny 18 year old was hard the whole time driving back. She liked my car and it was fast and really seemed to enjoy riding in it. She asked me to pull over on the side of the road. I did. She looked at me and asked if I had a big dick. She asked because, I am very tall, (6'9") and she wondered if my cock was big too. I was a bit embarrassed to say but said I guess so. She said, show me. I still don't believe I did but I was quick to unzip my pants and show her. She said the car and the sight of my erect cock has made her wet. She said lets get to the house quickly and have some fun.

We got home and my friend still hadn't returned. She asked me to get naked and she laid down on the bed. I was so hard and hot for her. I was so excited at my first female encounter. All my previews encounters were with guys. I was so ready for this. She looked so good and I thought what a great day for me. I laid down next to her and she reached for my cock. I was worried I might cum too soon. We kissed deeply and very passionately. I started to feel her tits and ass.... she reached down and removed her pants. My hands quickly moved to feel her hot pussy. She leaned down and started to suck my cock. I was feeling the best I ever had. She really was enjoying my young hard cock. The she stopped and climbed on top of me and had me slide my cock into her very wet pussy. She threw off her shirt and her beautiful tits were so exposed and looking so good and she fucked me. The feeling I had and the site of her were just to much. I started to moan and moan loudly. She knew I was cumming and she fucked me harder talking to me as she rode me. I came inside her and she kept fucking me. seemed like my cum just kept oozing out as she rode me.

She laid down on me breathing very hard. Soon she rolled off of me and asked me to eat her. I hadn't had much experience with that and I told her that. She said she would teach me. It was wonderful to enjoy her pussy. She told me how she liked and how to make her feel good. I got a good rhythm going and could tell she was enjoying it. I could feel her legs tighten as I was eating her. She started to buck and moan wildly and and she came about 4 times. We laid there for a bit so she could catch her breath. She went into the bathroom and I got dressed. My friend got back and a half hour later. What a great day for me. I think of her often even though I am almost 70 years old. She was so good for me and I learned lots from that day. Still use those skills today with my wife.