I had just had sex for the first time at the age of 30 (I wrote about it [here](https://www.reddit.com/r/gonewildstories/comments/abj88b/mf_losing_my_virginity_late_and_finding_out_that/)), and the next time I met up with her was a meetup event three nights later. After the event, we went for a walk around the city, talking about what happened. I reiterated that I didn’t think I wanted a relationship with her, and she said that was fine and wasn’t expecting anything of me either. I also mentioned that I was pretty bad at sex since it was so new, and of course she laughed and said that she could help me with that. We continued walking, with intermittent make-out sessions, and made plans to meet up the next day. Before parting ways, she gave my semi-hard cock a quick squeeze through my jeans.
The following day, I woke up with pretty much one thing on my mind. I teased myself by watching a bit of porn that morning. I hadn’t jacked off since the night we had sex 4 days prior, so my balls started boiling pretty quickly and precum starting leaking out. I stopped myself there, and spent the rest of the day counting down the hours until her arrival.
She finally came over in the late afternoon. We resisted jumping on each other until we sat down together on my small couch. We started making out heavily, and my hands started roaming over her body. Pretty soon I was kneeling before her seated body. I lifted her shirt up and started kissing the smooth skin of her flat belly. I slowly moved up as I kissed her and told her that she had an amazing body. I reached her bra, lifted her shirt higher, and flipped her bra up to expose the dark nipples of her small breasts. I got in several licks and she moaned softly several times. However, she put her hand on my head and told me that first she wanted to work, meaning she wanted to practice a foreign language a bit with me (that had been her original reason for starting to come over to my place).
I let up, and sat back down next to her on the couch and helped her with the language. As soon as we finished what we had agreed to go over, I closed her book and turned to look at her. She said with a sly grin, “Wait, we aren’t finished yet!” I told her that yes, we were finished with that, as I put the book away and moved my face to hers. Our lips met and it was on. My lips and hands roamed around her body. This time, I lifted her shirt up and took it all the way off, fully exposing her bra. My shirt and her bra both came off. She had been rubbing my cock through my jeans, so she pulled them off with my boxers. She quickly got up off the couch to kneel between my legs and start blowing me as I reached down to play with her nipples. After a few moments of that, I pulled her up, slid off her panties, gave her ass a few squeezes before my sliding my fingers inside of her.
We stood like, my cock in her hands and my fingers in her pussy for a bit before I said “Let’s fuck!” She grinned and said OK! She went to lay down on the bed and I went to grab and unroll a condom on my wet cock.
I got in between in her legs and began that wonderful first push inside her. I can still remember that arch of her back as I completed my first thrust. I began thrusting in and out of her slowly and, of course, awkwardly. As I explained in my first story, the combination of the nerves and the condom and likely death grip, I just wasn’t getting enough sensation on my cock while I was fucking her. It was still fun though, and I flipped her over to try some doggystyle. She was encouraging me throughout, softly moaning and telling me that I felt good inside her, even coming during doggystyle (though sometimes I wondered if she faked it?).
Even after having her turn back over for missionary, I really felt like I wasn’t going to be able to cum, plus I had some other ideas. I slid out of her and said “I want to try something”. I pulled the condom off, and started jacking off over her.
“Oh you want to cum all over me?”
I nodded yes, and kept stroking my dick. I felt the elusive orgasm rising within my balls and soon as I unloaded four days worth of cum all over her. The first spurt even cleared her body to land on the sheets. As my balls finished draining, there was a line of cum between her breasts down to the pool beneath from my cock was resting on her stomach. She got up to go get cleaned up in the bathroom, but before doing that, she turned around and starting rubbing my cum over her body saying “Oh I’m a dirty girl now!”
We got cleaned up and went out to grab a quick dinner. We were both pretty quiet while eating, I guess that’s what happen when the lust fades away and you don’t have the bond of a relationship. However, when we got back to my apartment, she practically jumped back on me as soon as I shut the door. This time, we got undressed standing up, and I had my first practice with trying to unclasp her bra from the front (it took me a bit of time). We were quickly naked again, with our fingers wet with each others’ juices. She looked at me and said “Fuck me again.” I didn’t need to be told twice, so I unrolled another condom (my last one) on my cock and we got back on the bed to begin.
This time, I really wanted to cum inside her, and she really wanted me to as well. As I pounded her, she was moaning my name and telling me she really loved the way I was fucking her. She grabbed my abs and told me she really liked that part of my body. She ran her hands through my pubes and pulled on them. When I started fucking her doggystyle, she said she loved the way my balls were slapping against her pussy. When I entered her after switching positions, her head rolled back and she started speaking in her native language (that felt pretty good). At one point, with her back on the bed, instead of having her spread her legs, I put her legs together and straight up, hoping the extra tightness would help me cum. I started to feel a little tingle in my balls, but I just couldn’t get enough friction and sensation on my cock to maintain that sensation.
Finally I pulled my cock out of her (after 15 or 45 minutes, I had no idea), and started fingering her. She must have thought I was unhappy with how wet she was, so she said “It’s normal that I’m not as wet anymore, just keep fucking me and it will come back.” I got back inside her for a few thrusts, before she finally got fed up. She kind of pushed me off her and said that she needed to stop. She went to the bathroom to clean up, as I was left sitting on the bed.
I didn’t really understand what had happened, but she came out of the bathroom, not naked anymore, and sat down on the bed next to me to talk to me. She was obviously frustrated that I couldn’t cum and asked me if I had mental problems. I was a bit confused, so she said that she had read that men who wait so long to lose their virginity often have mental issues. I said that I thought it was kinda normal what was happening to me and that I was pretty sure that I didn’t have serious mental issues. Anyway, it was pretty weird as we got both in bed to go to sleep that night.
Even after all that, she couldn’t keep her hands off me, and I was still horny, so I returned her groping. This time she said “Let’s watch porn together,” obviously thinking it would help me cum. I got my laptop and pulled up one of my favorite videos. As we watched, she stroked me, trying to draw that cum out of my balls. I told her that I wanted to see how she masturbated, so she moved her other hand to her pussy and started thrusting her middle finger in and out while I squeezed her ass.
This setup seemed to be working for me as I really didn’t take long before I felt my balls stirring. As the flame began to light up, I turned my head to her and could only manage to say “Ok…ok…ok!” She sensed the finish line and started stroking harder and harder as she started to moan “Yes…yes!”. Finally, the dam burst and I erupted in her hand. As soon as she felt the flow of cum on her hand, she slowed down a bit, and started squeezing the head of my cock while I was coming. The increased pressure on my head during my pulses just about paralyzed me.
We cleaned up, and went back to bed, no more playing around that night. Unfortunately, she left in the morning before we could play around, but she ended up coming back later that day. Since I had no more condoms, we didn’t fuck, but she was able to jack me off to orgasm (with the same cock head squeezing technique) as she ground her pussy into my thigh, with my hands squeezing her perky ass.
As I said in my other story, the next time we had sex, I was able to cum inside her, so I did get a bit better at sex. Since she was my only sexual experience, I still fantasize about her as I masturbate over two years later and miss that feeling of anticipation when I was counting down the hours until she would come over to fuck.
Source: reddit.com/r/gonewildstories/comments/bruv5d/mf_long_and_frustrating_story_about_being