Before the days of Tinder were Neil Strauss and leagues of guys trying (mostly failing) to sarge, AMOG, and peacock all night long. This night started out like many others….approaching random girls, walking back empty handed, and laughing about the latest rejection. Hope was getting low, and I was starting to think this night may just end with late night pizza and binge watching Lost (yes, I was serious about this being before the days of Tinder).
Then, a girl I used to hook up with walks into the bar. 5’2″, 115lbs, nice round tits, short dark hair, 26 at the time, and the sweetest smile you’ll ever see. She was the type of girl you’d never think twice about introducing to your parents…she was smart, successful in her career, fun to be around, and down to earth.
I was excited to see her, but was pretty sure that feeling was not mutual. Brief history: we hooked up for 5 months after meeting at a mutual friend’s party. The sex was mind-blowing, but we weren’t in a relationship. I had just gotten out of a long-term relationship, so I made it clear that I wasn’t ready for for another commitment. After a night out (not with her), she calls me the next day and was like “Sooo…who was that girl on 3rd ave?” We didn’t see each other after that.
Back to the bar. “Hi. Long time!”
We spend the next hour catching up and drinking, and then, it dawns on me that we’ve been talking to each other for over an hour. She’s laughing. She’s having fun. She’s smiling at me. Wait…is she still mad at me? Is she just being polite? Or is she down for something more?
Turns out she was down, but her friends were giving me the death stare. I ask her to go to another bar with me…the classic “isolate her from her cock blocking friends” strategy. Works 100% of the time. She tells me, “I can’t help myself around you.” And we start making out…like the sloppy, 10 drinks in, I want to drink your saliva kind of make out.
Once we get back to my place, I was reminded of how much fun we had together. One of our favorite positions was one in which I would be on my knees on the bed…she would lie on her side in front of me and give me head while I fingered her. I loved the feeling of her moaning while struggling to give me head at the same time. I loved that I could control how fast she sucked on me simply by fingering her faster or slower. Sometimes, we would get into this position when I was ready to cum, and I would finger her as hard as I could, which would prompt her to vigorously suck my dick as hard as she could. Then, in the midst of intense moaning, I would fill her mouth with my cum. And she was not the type of girl to ever waste a drop of it.
So naturally, we got back into our go to position. Being very drunk at this point, I knew I was going to last forever and I was determined to make this night with her last.
She gave me head while leaning on her side, and I fingered her hard, enjoying the view of her head bouncing on my cock in perfect harmony with my two fingers moving in and out of her vag. I fingered her until she came, but even as she came, she never released my dick from her mouth.
After cumming, she collapsed onto her back. She had already been giving me head for at least 30 minutes. Although she was in good shape, staying in an almost side plank position while giving head for an extended period of time is pretty hard. She laid her head into the pillow, taking a moment to rest. I gently sat on top of her letting my balls press into her stomach. She stroked my rock hard dick with her cute little hands, and I massaged her tits while looking into her eyes. She and I both knew that I was going to fuck the shit out of her.
But not yet….I leaned down and sucked on her tits for a bit. Then, I straddled her and positioned her head against the headboard. Firmly placing my left hand underneath her chin and my right hand on top of her head, I pinned her head in place against the headboard and then eased myself in and out of her mouth. Slowly at first, then, working up to a pretty fast pace. If I was sober, I probably would have already cum by now, but I had plenty of mileage left.
I sat back into my heels and placed both of my hands behind her head. I pulled her head towards my dick, and she understood the change in position I was going for. Knowing she was going to be in this position for a long time, she wanted to get comfortable. She put two pillows under her head to prop it up and give herself a bit more support. She laid her head down on the pillow at the perfect angle for me, laid her arms down to her sides, and waited for me to get back on top of her.
Now that she’s ready, I straddled her up by her shoulders. From this vantage, the only thing visible to me is her head lying on the pillow and my dick which is about to disappear into her mouth. I then move my hands behind her head again. Simultaneously, I pulled her head down my dick (lifting her head off the pillow) and thrusted my dick towards the back of her throat. We had spent so much time in this position that I knew exactly how far she could take me without gagging. She had complete trust in me to not go too far and hurt her, which allowed her to completely relax and let me take over.
I never understood how she was able to give me head like this…although I refrained from gagging her, I didn’t refrain from how hard and fast I moved her head. Back and forth, I pulled her head up until her lips were 1 inch from fully deepthroating me (her absolute limit) and then pushed her head back down into the pillow…moving her head up and down my dick like an engine piston. With any other girl, I would have been worried about hurting her neck, but I knew that she was used to it. She knew how to breathe through it, she knew how to maintain suction in her mouth, she knew to ask for a momentary break when she needed it, she knew she didn’t need to worry about me gagging her….our bodies moved together in a perfect rhythm.
I kept her going at a steady pace. I closed my eyes, enjoying every thrust of my dick into her mouth. I zoned out and almost entered a zombie like trance. I lost track of time until she finally placed her hand on my stomach, stopping me from thrusting back into her mouth. She smiled as if I had just given her a Chanel bag and looked up at me and said, “My mouth is tired. I’m not used to giving this much head anymore.” (side note, we used to have very long blowjob sessions while we were hooking up, and she frequently talked about how I built up her endurance to give head for a really long time. When we first started hooking up, her mouth would start to hurt after 10-15 minutes, but towards the end, she could basically go forever…I tended to last for a long time since we usually hooked up late night after heavy drinking).
She motioned that she was ready for me to fuck her. I spread her legs and guided myself into her. And that moan of hers as I first went in…I’ll never forget it. It was as if she was feeling a dick go inside her for the first time. “You feel so amazing inside of me.” I started out gently fucking her in missionary while we enjoyed making out with each other. I then put her legs over my shoulders, so I could thrust harder and deeper into her. It didn’t take long for her to cum again. In the past, whenever we changed positions, she would give me head for a few minutes. She remembered that I loved getting head in between position changes. There is no better feeling than my dick seamlessly transitioning from her vag to mouth and back to vag and so on.
I laid down on my back, and didn’t have to say anything. She got in between my legs and went to town on my dick. I was rock hard and my dick felt huge in her tiny hands. I started to feel like I was getting close to cumming, but I still wanted to fuck her doggystyle. So, I got up and positioned her in front of me.
I gave her a firm slap on the ass before entering her from behind. She buried her head into the pillow, creating a beautiful arch in her back and accentuating the perfect roundness of her butt cheeks. I felt my tank getting ready to be emptied. I wanted her to cum again before I did, so I pulled out and started fingering her while she was still in doggy position. I fingered her hard, and right as she started saying, “oh my god, I’m going to cum,” I plunged my dick back into her and watched and listened to her cum. I always loved how she came…she would moan louder and louder until her climax and then let out several quiet sighs while her body involuntarily jerked.
She usually needed a minute to rest after an orgasm, but this was no time to rest. I was getting ready to bust so I kept thrusting. I grabbed her shoulders, lifting her off the pillow, which gave me leverage to push deeper into her. I moved my hands down to her tits and then used them as handles to keep pulling her body deeper down my dick. I felt myself getting closer, and grabbed on her tits even harder as I thrusted into her. She put her hands on my hands, and I realized that I was squeezing her too hard.
I moved my hands off her tits and moved my hands back to both of her shoulders, pulling her entire body as I thrust into her. I only needed a few more thrusts, but I didn’t want to cum on her back. I slowed down and asked her if she was ready for my cum, which she remembered to mean, “are you ready to swallow it?” When we were hooking up, we used to talk about swallowing. I asked her about her thoughts on swallowing…she didn’t care about the physical act. She didn’t like the taste but she didn’t dislike it either. However, she felt that the act was “intensely intimate”…she enjoyed being an active participant in my orgasm rather than a bystander. She enjoyed “feeling my dick engorge in the final seconds.” She said she felt this innate sense of protection in that intimate moment…it felt primal to her. Caveman like. And practically speaking, she also thought the clean up was so much easier.
In her mind, the most intimate, intense, and logical conclusion to sex was swallowing…it didn’t make sense to finish any other way. There was no bigger turn on than knowing that it was something that she wanted. In between her moans, she answered my question with an affirmative “yes.” I asked her again, “are you sure? It’s going to be a lot.” She knew the question was a rhetorical one…but she replied nonetheless, “yes”
I pulled out, and she instinctively flipped around onto her back as fast as she could because I was about to explode. She flips over, I jump on top of her, and grab her head frantically. I stick my dick in her mouth and instantly start cumming. She is panting, trying to catch her breath while swallowing at the same time. If there is a heaven, I felt it in that moment. She sucked me for another minute or two…not a single drop spilled anywhere.
It was about 4am at that point, and we were both exhausted. I freshened up and I gave her some pajamas. We cuddled, kissed a bit more, and then passed out.
We woke up mid-morning and obviously I wanted to give it another go. My dick was incredibly sore, and my head was pounding. I was lying on my back with her arm around me and her head on my chest. I lifted her chin up and kissed her. I placed her hand on my dick, and she knew what I wanted next. She gets in between my legs, pulls my sweatpants down, and starts to suck on me….5 minutes, 10 minutes, 15 minutes. I keep slipping between having a decent erection to being semi-hard. My body was just way too hungover and tired and I couldn’t get super hard.
I grab her head and move it towards my balls, so she starts sucking on them. I thought this might help get me harder, but it’s not working. She grabs my dick with her hand and then puts her mouth on the head of my dick and starts bobbing up and down. She bobs up and down faster. I love her dedication. I’m able to finally get decently hard, and sensing her chance to enjoy all her hard work, she asks, “Do you want to put it inside me now?”
I get on top of her, and push my dick into her. She starts moaning, and I’m eager to fuck her brains out again. But my dick is just too sore, and I start to lose my hard on. I told her, “I’m sorry, but I don’t think it’s going to work.” To which she replied, “It’s okay. Just stay inside me.” She puts her hand on my cheek and pulls my head in for a kiss. I spend the next few minutes gently pumping her with my half erect dick and slowly kissing her. Eventually, I completely lose my erection, but we keep making out.
I felt bad that I couldn’t give her some morning sex and also didn’t want the fun to end, so I started fingering her while making out. I fingered her until she came, and then, she snuggled back into my arms. After some more time cuddling in bed, she says that she needs to head home. I asked her if we could meet up again, and she smiled and said, “Sure.”
I messaged her two days later to see if she wanted to meet up again, but to my dismay, she politely declined. She told me that she really enjoyed seeing me the other night, but didn’t think it was a good idea for us to see each other again. About two months later, I saw a post on Facebook of her and her new boyfriend…basically announcing that she was in a new relationship. I realized that she probably just started seeing this guy when we ran into each other, and she probably sensed that this new guy was ready for something more serious than what I was able to give her.
I was obviously disappointed, but at least, I had a fond, final memory of her.
Source: reddit.com/r/gonewildstories/comments/un198w/its_a_good_night_when_your_dick_is_too_sore_to
Lol my guy is selfish in bed for 2 hours straight and then is disappointed she doesn’t want to hook up again
Great story! Sorry you two couldn’t hook up again but it sounds like a great end. Hope to hear more of your other ones with different people.