I (M23) Did A Bad Job Taking Her (F22) Virginity, What Now? [Long But TL;DR]

Background

Prior to us dating we had been friends for 2 years and we never really talked about sex. She (F22) has been with me (M23) when I've gone "condom shopping", seen me with hickies and seen me with other girls I dated while we were friends. She know's I've been sexually active with two other women prior to our relationship. She has had boyfriends in the past however she said she was unable to have PIV sex with them because of "lack of foreplay". Our conversations never really went past that point because we kept it pretty respectful as friends.

Fast forward 2 years and we started seeing each other romantically. We've been together for around 3 months and had sex for the first time this weekend however it went badly. I was hungover from a party the night before, and drank with her in the hotel, which resulted in me getting whiskey dick.

The First Attempt

Although I set up the mood perfectly with a boujee hotel room, drinks, great view and sensual music the rest of the night was just awkward transitions between me losing my erection and her drying up while I was hard.

I tried giving her oral sex but she squirmed a lot making it really difficult for me to concentrate on her clit. I tried fingering her but I could hardly get 1 finger in. I tried playing with her clit, and she guided me a bit but she dried up really fast.

The Conversation

I blamed myself for it because I didn't manage my drinking from the night before. I also felt pretty unattractive for the first time in bed. I mean I'm a 6'0 dude with a good physique, decently visible abs. I spend a lot of time touching, kissing and sweet talking the girls I sleep with so I've never had a girl dry up on me like that.

However It seemed like she really took it harder that I did. She opened up about how she had "vaginismus" due to being sexually assaulted in the past. She broke down in tears because she was really excited to sleep with me but the mental block was too strong. She said she was worried I'd cheat on her or leave her because we can't have sex.

I told her I liked her all the same and I was willing to work with her through anything and that I would never leave her for something like that. We cuddled and went to bed.

The Second Attempt

She woke me up in the morning rubbing my back, we started making out and I took her over to the couch. She took off her clothes and started rubbing her clit on my dick. She said she was embarrassed because she couldn't get wet and "felt like an old woman" because she needed lube. I told her there was no shame in using lube and that I wouldn't judge her for her. Little did I know she packed some, so she ran to her bag, grabbed it and put some on herself and me.

Heres where things got intense because she really tried and struggled for a good 5 minutes to squat onto my dick. I told her she didn't have to but she really pushed herself. I held her tight and I could feel her shake and sweat but eventually she did it. She was so impressed with herself, and I was pretty shocked too especially because I could hardly get a finger in myself. She slowly rode me on the couch and she got more wet, and picked up the pace. I fucked her up against the glass window (she's 5'0 and petite). Threw her onto the bed, and we fucked in missionary, then I turned her around, grabbed her by her hair and fucked her in doggy (It felt like 8 minutes all together). I came on her butt, wiped it off.

Pillow Talk

She said she never expected to be able to have sex sober, and without music. She was really happy. I told her I was proud of her and that I was glad we shared an intimate moment together. She actually thanked me which was kind of a shock.

​

TL;DR & My Question

TL;DR: I had sex with a friend who had vaginismus due to a traumatic sexual abuse experience in the past. We talked about it, she really pushed herself and was able to over come her insecurity and fear and we had (awkward but great in my opinion) sex but I wasn't able to make her cum.

I feel like I did a bad job with her first time because I never gave her an orgasm. Usually I'm pretty consistent with oral sex, and fingering and can usually give a girl 2 orgasms before I get mine so I'm wondering how to approach this level of comfortability with her. What are the next steps knowing her condition?

Submitted October 09, 2021 at 12:02AM

BackgroundPrior to us dating we had been friends for 2 years and we never really talked about sex. She (F22) has been with me (M23) when I've gone "condom shopping", seen me with hickies and seen me with other girls I dated while we were friends. She know's I've been sexually active with two other women prior to our relationship. She has had boyfriends in the past however she said she was unable to have PIV sex with them because of "lack of foreplay". Our conversations never really went past that point because we kept it pretty respectful as friends.Fast forward 2 years and we started seeing each other romantically. We've been together for around 3 months and had sex for the first time this weekend however it went badly. I was hungover from a party the night before, and drank with her in the hotel, which resulted in me getting whiskey dick.The First AttemptAlthough I set up the mood perfectly with a boujee hotel room, drinks, great view and sensual music the rest of the night was just awkward transitions between me losing my erection and her drying up while I was hard.I tried giving her oral sex but she squirmed a lot making it really difficult for me to concentrate on her clit. I tried fingering her but I could hardly get 1 finger in. I tried playing with her clit, and she guided me a bit but she dried up really fast.The ConversationI blamed myself for it because I didn't manage my drinking from the night before. I also felt pretty unattractive for the first time in bed. I mean I'm a 6'0 dude with a good physique, decently visible abs. I spend a lot of time touching, kissing and sweet talking the girls I sleep with so I've never had a girl dry up on me like that.However It seemed like she really took it harder that I did. She opened up about how she had "vaginismus" due to being sexually assaulted in the past. She broke down in tears because she was really excited to sleep with me but the mental block was too strong. She said she was worried I'd cheat on her or leave her because we can't have sex.I told her I liked her all the same and I was willing to work with her through anything and that I would never leave her for something like that. We cuddled and went to bed.The Second AttemptShe woke me up in the morning rubbing my back, we started making out and I took her over to the couch. She took off her clothes and started rubbing her clit on my dick. She said she was embarrassed because she couldn't get wet and "felt like an old woman" because she needed lube. I told her there was no shame in using lube and that I wouldn't judge her for her. Little did I know she packed some, so she ran to her bag, grabbed it and put some on herself and me.Heres where things got intense because she really tried and struggled for a good 5 minutes to squat onto my dick. I told her she didn't have to but she really pushed herself. I held her tight and I could feel her shake and sweat but eventually she did it. She was so impressed with herself, and I was pretty shocked too especially because I could hardly get a finger in myself. She slowly rode me on the couch and she got more wet, and picked up the pace. I fucked her up against the glass window (she's 5'0 and petite). Threw her onto the bed, and we fucked in missionary, then I turned her around, grabbed her by her hair and fucked her in doggy (It felt like 8 minutes all together). I came on her butt, wiped it off.Pillow TalkShe said she never expected to be able to have sex sober, and without music. She was really happy. I told her I was proud of her and that I was glad we shared an intimate moment together. She actually thanked me which was kind of a shock.​TL;DR & My QuestionTL;DR: I had sex with a friend who had vaginismus due to a traumatic sexual abuse experience in the past. We talked about it, she really pushed herself and was able to over come her insecurity and fear and we had (awkward but great in my opinion) sex but I wasn't able to make her cum.I feel like I did a bad job with her first time because I never gave her an orgasm. Usually I'm pretty consistent with oral sex, and fingering and can usually give a girl 2 orgasms before I get mine so I'm wondering how to approach this level of comfortability with her. What are the next steps knowing her condition?