[MF] I Had My First One-Night Stand and I Took Her Penetrative Virginity (kinda long)

This Saturday morning I had my first one night stand.

A few weeks prior a friend of mine, Tess, really opened up to me about her sex life. It was really interesting to me because no girl had ever been as open with me about their sex lives before this. She told me all about what she liked, didn’t like, size comparisons and everything. She also felt comfortable telling me all of this because I was happily in a relationship with my then girlfriend at the time.

Last week on Wednesday I was robbed, and then the day after on the Thursday my girlfriend broke up with me with the reason being I was too angry about being robbed and not in a good place for a relationship. Then on Friday it was my birthday. I saw Endgame because it came out that day so it was an okay end to my week.

I told Tess that I was broken up with and also moving back to her city because I was starting my next school term there the next week. She told me that her and some friends were going to go out partying during the second night I was back. I told Tess jokingly to let me know if any of her friends wanted a tall blonde guy if they hadn’t found anything by the end of the night. I didn’t actually expect that to go anywhere but at 4AM on Saturday morning I got a message.

“Hey, are you still awake?” Tess asked me.

“Surprisingly” I replied.

Tess then went on to tell me about how two of her friends had seen pictures of me and really wanted a dick to suck. I was suddenly very nervous and excited at the same time because I hadn’t done anything ever outside of a relationship and there was the potential of me having two girls spend the night with me. Unfortunately, one of them called her FWB but the other one was still down. So I thought “I should try this at least once” and I showered and headed over to Tess’s place to pick her friend up.

Once I got there I messaged Tess to let her know I was in her building’s parking lot. She walked down a few minutes later with her friend, Mary. Mary was tall, fit, and had the biggest boobs and the second biggest butt I had ever had the pleasure of measuring with my hands. She got into my car and we made small talk while we drove the 8 minutes to my place.

Once we got there I told her that I was kinda nervous and she told me that’s okay and then kissed me. She wasn’t the best at kissing, but I thought “This won’t last that long, she just wanted a dick to suck right?” She got me to suck on her nipples and she absolutely loved that, and she held me tightly as I sucked on each one. Eventually she wanted me to get naked so she could get what she initially wanted so I stripped down and she took my dick in her mouth. What she lacked in kissing skill she really made up for in dick sucking skill. She took the whole thing in from bottom to top and played with my balls to which had never happened before.

I didn’t want to be the only one on the receiving end so I asked her if she wanted to 69. She told me that she didn’t shave but I said that didn’t matter so she dropped her bottoms and I went down on her. This is when I learned just how important it is that both parties shower before doing anything sexual.

She smelled like piss. Just reeked of it. The smell stayed in my room for over a day later. But I was a trooper and I went down on her anyway. For a while at least. I asked after a bit if she had a condom so we could still do something fun that didn’t involve me so close to the pee smell and she told me she didn’t. Unfortunately the guy who robbed me stole all the condoms from my room in my last place so I didn’t have any either. So I messaged Tess and asked if I could grab one from her since it was now 5AM and every place that sold them was closed.

So I drove over to Tess’s place and when she was giving me the condom she told me to be really careful. I said I normally was, and asked why she was stressing it so much. Tess then told me that Mary had never been with a guy before. Confused, I asked her to elaborate. Tess told me that Mary had been with several girls before, but had never had penetrative sex with a guy so I should be extra careful. I took this to heart and then drove home.

Once home again I asked Mary a few times to make sure she wanted to do this, and I got a resounding yes so I put the condom on and started up. She was super tight. It probably took at least five minutes of me working myself in inch by inch before I could fully fit inside. My favourite part of this was when she asked me “Is it fully in?” when I only had about 2/3 of it in and I told her that and then she just mooned yes.

I started going slow, just sliding all the way in and then out to get her accustomed to having a dick in her. After a while I started going faster and faster and she told me to go harder so I did. I was pounding her fast and hard when she told me she wanted me to stop to try doggy style instead. So she turned around on all fours and I entered her from behind. This didn’t really work as well as I had hoped because she kept angling her back up and I kept falling out so she got on top of me instead.

She wanted really to just try all the positions she could so she rode me while I fingered her clit a bit from the front until it was to much for her so she turned around and got me to spank her while riding me reverse cow girl. She then said she was tired and she wanted me to get on top again. We’d been going long enough that she’d dried up a little so we lubed me up with warm water and went back at it. While I was doing her missionary she asked me to choke her. I had never done that before so I did some light choking but she kept on tell me to grip harder and pound her harder. Then without warning she came and squirted all over me and the bed, which was another first for me. I was tired out and she seemed like she was too so I lied down and she cuddled up to me.

In the morning I drove her to the bus station so that she could catch her bus to her city, and then immediately washed my sheets and myself. All in all, it was really cool to have sex with someone who I knew for less than an hour beforehand and I’m glad I had that experience, but I don’t really think I’d do it again. It helped me stop thinking about my ex for sure, but I definitely think that sex is better with someone you really care about.

Source: reddit.com/r/gonewildstories/comments/bl3lp0/mf_i_had_my_first_onenight_stand_and_i_took_her