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First time poster here, I hope you enjoy my story. Feedback is appreciated

I (25M) lost my virginity two weeks ago. After many unsuccessful tries at online dating and hurt feelings, I recently matched with a woman (F28) on a dating app. Since I wanted to get out there a bit more, I asked if she wanted to go out and eat at a restaurant right out of the gate. She agreed and we set a date in a few days’ time. Afterwards, while still talking she asked if we wanted to watch a film together at my place. This already was the quickest I had ever set up a date and I was amazed that she wanted to do more than a simple restaurant visit on the first date and agreed. She followed up by asking if we could hold hands to which I agreed. She followed that up by asking what could happen afterwards. This is when I panicked as I had never written to anyone over sex before and was surprised to have entered that territory after a few hours with her.
I answered that we could how the evening goes to which she agreed, however being horny and having a rock-hard penis, I continued writing about sex with her. We talked about what we liked, which toys we enjoy and her favorite positions (doggy and cowgirl) while I masturbated to our comments. After cumming, we cooled down and wrote about other stuff looking forward to our meeting later that week.

The date was alright, food was good, we vibed ok and the film was great. After a couple of minutes at my place, she already hugged me and got close to me, which led to several erections over the course of those two hours. Afterwards she didn’t make any move to leave so after a while, I asked her if she wanted to kiss. She closed her eyes and agreed, which was when I started kissing her. Her mouth was ready for it and even though my kissing was very rusty, we quickly exchanged tongues, bit and sucked on each other’s lips while we both started to moan. It became more intense and I asked if there was any place that she wanted to be touched. She replied her breasts, so I started to touch her body, especially fondling her breasts. After a couple of minutes I slipped my hands under her bra and freed her enormous breasts. I am a pretty skinny guy and her natural, coffee-skinned breasts were almost as big as my head. I asked for permission and started sucking on her breasts and nipples and I couldn’t stop. I kissed her right nipple while fondling the left one, sucking, nibbling and caressing them at turns, while she was absolutely ecstatic. She asked if we wanted to proceed to the bedroom to which I agreed.

I was completely amazed as I knew I was finally about to have sex. We arrived and got undressed, only wearing socks and boxer shorts / panties. We started making out again but soon that wasn’t enough anymore and our hands wandered toward our legs. I slipped a finger into her, soon followed by two others while her pussy started making delicious wet sounds. She seemed a bit uncomfortable about it but I calmed her and said that I enjoyed it. at the same time she pulled my foreskin down and jerked me off touching my sensible head in a way that hurt a little but felt really good, I was close and she seemed to enjoy herself as well. She asked if I wanted to put a condom on and proceeded to put one on me which turned out to be too small ( I had bought a pack of novelty condoms not looking up the sizes), so I changed to another better fitting one. Then I proceeded to lay myself on top of her and put my penis into her wet vagina, while she helped guiding me in. It was different than I had imagined, she was wet and warm but I couldn’t fully enter her so I mostly moved my hips while we continued to suck on each other’s lips. Since my hair is pretty long it often got in our way but we didn’t mind and devoured each other’s faces not minding the dozens of hairs we kissed along the way, which really turned me on. I noticed that the penetration wasn’t going anywhere so I asked her to switch to cowgirl.

I laid down and she went on top of me, but again the insertion didn’t quite work out. I wasn’t quite that hard and she seemed to be mentally blocked as well. She jerked and sucked me off, which was another first for me while I played with her clit and nipples. We both noticed that penetration didn’t seem to lead anywhere but we were still very horny so she proceeded to take off my condom and jerked me off. I finally came after a couple of minutes and it felt great ejaculating while feeling the warmth of another body next to me, hands fondling my balls, my dam and my head. She asked if she could taste me, to which I agreed. She she scooped up a bit of my sperm and licked it, which I wondered was very hot. I quickly showered and went back to bed, telling her I wanted to reciprocate the favor.

Since insertion seemed to be a bit cursed we put on our underwear and I laid down while putting my upper legs between her legs. We proceeded moving like we had sex, me becoming finally dominant. I whispered into her ear that I wanted her to cum, while she left enormous smooch marks on my neck. I had my hands on her butt, moving her up and down in a way to maximize the friction between her legs. We were super sweaty and tired at this point but I didn’t stop moving my leg on her clit until the told me absolutely exhausted that she had come. We let ourselves fall after that and talked a bit about what we liked and proceeded to fall into a short sleep. I hugged her, being the big spoon and noticed that I got super hard during the night, which I provocativly pressed against her big butt.

Needless to say after a few short hours neither of us could hold back our horniness, so soon I started fondling her breasts, while she played with my penis. It felt special since this time we were doing it under the covers and in the dark. After a long make out time, we both tried having sex again which still didn’t quite work. I jerked myself off while she had her hands around my balls and later I inserted my purple vibrator dildo into her pussy. She didn’t quite finish this time but we were absolutely exhausted having had sex for 4 hours while only sleeping about 3 hours between that.

We would go on having sex a week later still encountering the same penetration problems, but still it felt like heaven having my first time seeing a naked woman, having a blow and handjob, trying my first sexual positions and feeling an aroused and wet pussy on my penis and fingers. Not to talk about causing an orgasm for another person for the first time, making out, moaning into our mouths and so many other firsts. I have become more active now, bought a couple of toys and hope to be able to have real penetrative sex soon, being able to fully insert my penis into a vagina and being able to cum inside.

TL;DR: Met a woman on a dating Plattform. After dinner and movie we had sex and I finally lost my virginity. We had rouble with penetration but still enjoyed each other’s bodies and business.

NSFW: yes

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