Was your first time awkward or enjoyable for you? What would you change, if anything, if you could back in time and relive the experience over?
It was both, awkward at first, I was too young and had no idea what I was doing. I am a quick learner and before it was over, very enjoyable.
Just kind of happened. We'd been "fooling around" for a long time leading up to it. Genital contact with no penetration and that sort of thing. Then, one day while fooling around on my bed, she took it in. The early "fooling around" was awkward but by the time we finally started having intercourse, we were pretty comfortable together.
I do wish I had started having sex earlier in life. I was 24 and in grad school when I started with my first, to whom I am still married.
I would have to say a little of both. We were playing shot or shirt while playing strip poker. If you lost you could take a shot of liquor or take off a piece of clothes. I was down to my bikinis and she was down to her bra and panties. I got hard seeing her big tits and her black panties. After i lost the next hand i took off my bikini underwear because i was starting to get a little buzzed and didn't know if i was going to be able to go on. She lost the next hand and took off her black lace bra. WOW those tits were big and nice and her nipples were hard. She asked me if i like them and i said yes. Next hand she lost and took off her panties. After that i leaned over and started to kiss her and then the rest was natural. I did shoot my load in a minute or two like everyone told me i would. It felt great. We did it again in the morning and she left for work.
We were both virgins at the time so I guess clumsy was a word to describe. The biggest pleasant shock for me was seeing a mature girl naked for the first time . Seeing girlie magazines and even on the screen is so much different than the real thing.
Awkward, yet a very enjoyable thrill. Clearly she enjoyed it too, making it all the more satisfying if no less awkward.
It was an enjoyable experience that didn't occur until I was in my mid 30s. However that being said, I would go back & change the fact that I never finished. I'm not sure if it was the nervousness of not wearing any protection, or the fact that I wanted to go for as long as she wanted me to & I wanted nothing more than to to please her, or (the most likey reason) that I had only ever finished through masturbation, but she kept asking me to cum, but for some reason I just couldn't finish. Even the the times we spent over the next few weeks together, I never was able to finish.
"Imagination is more important than knowledge. Knowledge is limited. Imagination encircles the world."
- Albert Einstein
My first time was enjoyable and as I far as I could tell, that feeling was mutual.
There were some awkward parts in that I had zero idea as to what I was doing and figuring out the right position and angle for missionary was far more difficult than I had anticipated. Fortunately, we both got there quickly and did so multiple times that night.
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Both. We were both virgins so I was terrified for her, what it would be like, hell, would I pop before I got inside her? There were so many things I was afraid of and every one of them raced through my mind the day leading up to the deed. I didn't have a condom and I knew we were going to do it anyway, so yeah, I was afraid I would get her pregnant. The thing was, that night we knew we would have the perfect chance and we both wanted to do it so badly nothing else mattered.
The act itself was amazing though. I can remember it vividly even today. I remember how amazed I felt once I was inside her. Not just the physical feeling if it, but the emotional impact of knowing this was a huge moment in my life. When I came, I never even considered pulling out. I know she enjoyed it at the time but she missed her period after that and we thought she was pregnant. She told her mom and that was it. Thankfully, she wasn't but after all of that, I can look back at that summer as the moment I grew up. I dearly hope she remembers it fondly as well.
So, yes, awkward and wonderful. Both in extreme measure
Somewhat awkward, as a young teenager the first time in a warm moist pussy, I shot off so quick. However, being a young teenager I was quick to reload and lasted much longer the 2nd time.
So Lindsay (18) and I (19) were in my college dorm room bed, disrobed, we agreed to fuck: I got up and went to my clothes drawer and was fumbling around in the dark for the condoms I'd daringly purchased earlier and stashed. She said "Don't worry, I'm on the pill..."
So I dashed back to the bed, hard as rock and horny as hell, got most of the way inside her, and ****exploded****! She laughed (nicely), and so began our sexual adventures, which were wild and exciting. We were together a year. She had had a boyfriend in HS so it wasn't her first time.
What a memory!!! No I wouldn't change a thing! We explored sex with each other a lot in that year, and I got very comfortable with my desires, discovered I absolutely loved eating her pussy, and had many many sex-filled mornings, afternoons, evenings, and nights with her.
I suppose awkward because I was scared shitless, a skinny shy kid with the prettiest, most popular girl in school.
I'd have to say both awkward and very enjoyable, but I don't remember it being either one for very long. Fortunately, there were many more enjoyable interludes after that first one, most less awkward because it wasn't the first time, and often wasn't in the back seat of a car.
But yes, that first slide into a warm, wet, willing pussy is indescribably special.
Slightly awkward and completely enjoyable! She was about 10 years old and led the way... My only regret was not staying the night and having an amazing morning as well!
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It was quite awkward for me. Being young and stupid I had built up so much expectations about how it's gonna be and then I ended up cumming a minute into it. I hadn't told my partner that it was my first time (big mistake), so she also ended up looking at me confused. It took a few times until I was able to get out of my head and just enjoy being in the moment
It was surprising for one thing. I had not planned for it to happen, certainly not the way it unfolded.
It was awkward for me, as I was a 17 yr old virgin who had just started dating this girl who was younger than me, but years more experienced than I was.
Fortunately, she was both quite carnal/passionate and yet gentle/compassionate at the same time.
Looking back, I doubt that I could have surrendered my virginity to a better/kinder partner in a more comfortable scenario. And she was probably the hottest young woman in my entire HS. A real farmer's daughter, she was toned, fit, petite with an ass that would not quit. And quite pretty in that clean/scrubbed/fresh - country-girl way.
Mesmerizing hazel eyes.
She made everything fun.
The same GQP demanding we move on from January 6th, 2021 is still doing audits of the November 3rd, 2020 election.
My first time was both awkward and enjoyable.
I knew a thing or two from watching porn, and I had done "everything but" up to that point, but when it came down to actually "doing it" I was still a little clueless. Lucky she was too so we were both feeling equally awkward about it. Once I penetrated her and got the hang of basic thrusting it went really really well. I had no idea it would feel as good as it did. She was incredibly tight and wet.
Would I have changed anything? For one I would have gotten better condoms.. she got them and they were un-lubricated . So that sucked... second I would have put a towel under us. There was no way I would have been able to explain to my mom why there were little blood streaks on my sheets so I had to sneak them into the trash the next day (she was a virgin too).
I'll add that we both learned quick and by the third time she was riding me like a champ, or I was doing her doggystyle.
Awkward as hell - We were both virgins and only new what went where - getting it there proved more difficult than we ever imagined. If I had to do it all over again I would have offered up my virginity to an older experienced woman.
My first time was with a woman much older than me. She suspected her husband was cheating on her so she brought me home for revenge sex. It was all very awkward, and I was nervous he was going to come home and catch us. She maintained he wouldn't. After we had sex I regretted it. I don't think either of us enjoyed it, and I don't think she came either. I left after I came, which was selfish, but that's what you get for fucking a virgin who didn’t have much sense.
If I could change it, I wouldn't have had sex with her and instead enjoyed having sex with someone, somewhere where I was comfortable.
21 in the military and a film crew came to the base. A lovely young 30+ woman took me to her room, we shared a bottle of wine, the sex was awesome with her confidence. Loved it 3 times that night but took too long after that night to happen again.
She was a junior in college, I was a freshman. I was not her first. It was in my dorm room . . . right by the stairwell, rather distracting.
Unlike most firsts, where the guy is on top, she was on top.
We remained a couple for a year and a half. I never proposed, but planned to when out of college.
She dumped me out of the blue. I later learned she was bi-polar (but on medication).
It was ok. She knew it was my first time. Once I shot that first cum, I pulled out and she blew me back up and then we had better sex on the second go.
we were young it was awkward but the first time is wonderful
I'll let you, Gentle Reader, judge how enjoyable it was.
I was a virgin college freshman, and she was an experienced high school senior. New Year's Eve at my parents' house in my room. My parents were out partying. During a hot and heavy make-out session, she asked me to make love to her. Oh, by the way, she said she was just finishing her period but that wouldn't be a problem.
We got naked, I got on top, I pushed into her, took about three strokes and came. Then we washed and dried the bloody sheets and remade the bed.
"the Great God (snicker)" - James 'Bear' Llewellyn
Mine was a set up by my best mate for my 17th. It was awkward cos I had no idea what I was doing and she did. Then after he walked into the room and leant against the dresser going on about how it's not all it's cracked up to be.
With hindsight, the worst bit was her agreeing with him. lol
It was both awkward in that I really had no idea what I was doing as I was relatively young but also enjoyable, after all it was my first time.
I can still remember that night. It was incredibly awkward.
However, we were both ready and when I slipped inside her it was incredibly wonderful.
Her pussy was so warm and wet, I wish I had tried to experience that feeling longer.
We got plenty of practice (and much better) after that.
) , after we got her we went to a secluded area and Jerry signaled me out and Mike and Cheryl stayed in,soon I sawMikes naked ass going up and down and thought "Oh shit". He finished then it was Jerrys turn.Same thing, then, it was my turn. Realize please, at this time, mens magazines did NOT show vaginas. I got in the back seat (it was pretty dark ) dropped my pants and laid on her and told her to "put it in" she giggled and said she would fuck a stranger but not touch his dick. I finally found nirvana and went balls deep, she screamed out "holy shit Mike, you been holding out", about 3 minutes later I wasn't a virgin. 
