This happened a bit ago. I posted on reddit looking for someone and I got a response. We started out chatting. We had a few things in common like our love for science fiction. During the conversation she disclosed that she was a virgin and was looking to rid herself of that status. We agreed to meet the following day at the mall. At the end of work I made it out there to see her.
We had not exchanged photos but we decided on what we were going to wear. We decided to do this covertly. We even had a password. She had on a red dress. I was wearing a dark button up shirt and long pants. We both decided to wear all black underwear. We met and started talking. It was fun to play a little to try and seduce her to my bed. She seemed fine but then she said she was a little nervous and didn’t know what to talk about. I suggested we try the 36 questions on falling in love with someone. We got to question 12. At that point in time I asked her if she wanted to go to my place. She agreed.
We then drove to my place. When we got to my place we mostly went right into the bedroom. I prepared for her arrival. I set out some candles and matches. The sun had fallen so it was dark and I lit the candles. I also put on some soft rhythmic music.
We started with a kiss. Still standing, I started to take off her dress. Her dress fell to the floor. She did have on black matching bra and panties. The panties were also satin. She unbuttoned my shirt. It too fell to the floor. Next my undershirt and pants. I was then also in black boxer briefs. I took her to the bed. She was shaking a little. We held and kissed a little. I kissed her neck. I then took off her bra. I played with her breasts and kissed down her stomach. I then kissed around her hips and touched her through her panties. I went around her panties and touched her clit. I think she came at this point in time. I took off her panties and went down on her. I took off my boxer briefs. We held each other a bit more. Kissed. We talked. We got more connected. Listening to the music seeing the flickering candles. She touched me and seemed fascinated by my penis. I touched her too. She came again. I then went on top of her and took my cock and rubbed it around her opening. I could feel how wet she was. She was moaning in anticipation. I asked, “Do you want me to take your virginity.” “Yes, take my virginity.” With that and my cock went in. She gasped. I could feel the hoop of her hymen on my cock. She shuttered a little and said ouch. I asked her if she was fine and she said yes. I slowly moved my cock in and out. It was slow and gentle and we were speaking softly to each other.
We sort of fell into each others arms afterwards. I held her and asked her how she was doing. I asked if it hurt and she said not really. She felt something like a pinch and a stretch. It was unexpected but not painful per say. She also felt a lot of pressure in her hips but it felt really good. I touched her hair and reassured her. I touched her back in a soothing manner. I then told her to use the bathroom. That’s when I noticed the small spot of blood on the bed. We talked more and connected. Her being inexperienced, wanted to look at my penis more and sort of studied my cock. I told her where the sensitive parts were for me and she gently massaged me. She took my cock in her mouth and I guided her with my words on what to do. After that we had sex again. This time I went in deeper and rubbed her clit at the same time. She came very loudly twice. After she came the first time there I slowed down and felt her legs shake. When she recovered I got her to come again.
Personally I feel very vulnerable after sex with someone new. I told her about it and she was reassuring and we bonded more. We had sex again two more times or a total of four times. I am hypersexual so I can go several times in a day and I get really focused in when I am having sex. The last time we had sex, I took her legs back and went in really deep. Virgins often sort of "fight" when they are learning how to have sex. I mean they don't understand the body language and how to get more in rhythm of love-making. I taught her not to fight me and to let my cock slide into her more deeply. I have never forced myself on anyone. I always go for consent. Period! The fighting is not actual non-consent fighting. It is just how it feels from a male perspective.
I really only felt her hymen for the first two times we had sex. She said she didn’t feel a pinch after the second time and she felt some good pressure. The feeling of a hymen on a penis is a very specific feeling. It is tight and feels sort of a hoop around the cock. We then got dressed and I took her home.
Where I was feeling vulnerable the night before, she was feeling that way the next day. We chatted quite a bit. I told her this is normal and that sex is very emotional. I checked in on her all day and she was feeling better. We both mentioned how unfortunate it was that she felt that way the day after and not right after like I did. She was just so buzzed from the sex to have a freak out. She was also a little sore down there the next day. The day after she started feeling better and the day after that she was fine. We chatted for a bit on friendly terms and met up another time after that. We also agreed not to exchange names.
It was still very romantic. It was very sweet and we felt really connected. I love how slow and tender the first time was. I like how she explored my body and how I taught her about hers. I also like how connected we felt and how we were very concerned for each other's feelings. Also, it feels kinda naughty how anonymous it was.