A little backstory first. Good stuff starts under the dashes.
I met this girl my the summer before senior year of high school and she had just graduated. We dated throughout the summer but things didn’t get very physical. She was a virgin but had done hand stuff, so that’s as far as she was willing to let things go. We had a good time, don’t get me wrong. But, I wasn’t a virgin and being 18, I would get rather horny after making out and feeling each other up. One really awesome thing was that she would cum just constantly when I was fingering her! Of course, that would leave me all the more horny only to have her jack me off. She wasn’t even that good at a handy, but she really didn’t have to be. She was short, 5’1″/5’2″, 110lbs. very cute, nice curves, and somehow had c-cup tits that defied gravity like only an 18 y/o can. So, again, she didn’t have to give great a handy for me to have a good time.
We play all summer and I start back to school. She had gotten really attached but I still wanted to play the field and “enjoy” my senior year plus she wasn’t having sex with me or even a blowjob! She had used her mouth a couple times but would stop the moment she tasted a hint of precum which was like 5 seconds in. So yeah, I was a bit of a dick, but I didn’t want to be tied down and not having sex! So, we broke up. It was kinda messy but we lived far enough apart that we never ran into each other. That is, until about a year and a half later…
I was working at a mall and she came in with her family for Christmas shopping. We saw each other, chatted a little, and went our separate ways. A little while later, she comes back into my department to see me without them around, tells me she’s just broken up with the guy she was with pretty much the whole time since we broke up. Yadda yadda yadda, I get her number and we hang out a couple times just as “friends.” Well, that goes exactly like you’d expect.
We’re sitting on a park bench one night, just hanging out. The conversation has gotten kinda heavy. She’s been telling me about her ex. Not in a bad way, but talking about sex. Apparently, she had been really close to sleeping with me when I dumped her but was holding out for me to say “I love you.” So, when she got with this other guy, they jumped into bed pretty quickly. I’m not really the jealous type, so this was all fine with me to talk about. She was also telling me about how he never got her off and that I’m still the only other person to make her cum.
The conversation drifts around, she’s asking me about what/who I’ve been doing. I end up saying that I still like her. She sits, stunned for a moment. The smile dropped off her face. I lean in and we kiss. Slowly at first but soon wrapped up in a deeply passionate embrace. We stopped pretty quickly after we started, agreed that we should go on a date to see how things felt, and I walked her back to her car to say goodbye. I leaned in for a shoulder hug because I didn’t want her to feel my erection but she made me “give her a real hug.” Of course, as soon as she pulled me against her, she could feel how hard I was. She looked honestly shocked, laughed, and said “oh, we’re definitely going to have a good time!”
————–
So, I pick her up and we go out on our date to see a movie. We sit in the back, start making and pawing at each other before the previews are over. We alternate between watching the movie for a bit and messing around. I’ve got my hand under her bra playing with her sensitive nipples at one point before unbuttoning her pants and rubbing her swollen clit while she uses my neck to stifle her moans. We manage not to cum and straighten up before the end of the movie.
I was living with my mom and she was with her parents, so we really didn’t have a place to go to mess around. She still managed to convince me to go back to my apartment. We sat in the car in the corner of the parking lot and picked up where we were in the movie. Only this time, she finally started rubbing my cock.
“I think you should take me inside so I can use this.”
“Mmm, I would love to; you know that. But we can’t.”
Back to making out, my zipper comes down and she starts lightly stroking my cock.
“C’mon, let’s go inside. I want to show you what I’ve learned.”
“….we can’t. My mom is in there and she would kinda ruin the experience.”
She drops her head into my lap, licks the drop of precum off my tip, and starts swirling her tongue around my head. I sit back, explosions going off in my head. I never imagined things going this way tonight and really hadn’t considered how far she would want to go at all. I feel the pressure in my balls start building up and pray that she’ll go just a little longer. She stops.
“Please, let’s go inside.”
“Oh, God, I want to so bad!”
“Then let’s go!” With that, she takes me back into her mouth, sliding further down my shaft this time. This has already become the longest blowjob she’s ever given me.
I beg her, “please, keep doing that a little longer!”
She stops again, “I will if you take me inside.”
I’m not entirely sure how many more times we alternated from her sucking me near the edge and me rejecting going inside before my 19 y/o brain said fuck it and we went inside. Fortunately, my mom was working 12 hour shifts at this point, and would go to bed very early the night before. So, she was already sound asleep. We tiptoe across the apartment into my room.
Ravenously, we’re all over each other as soon as my door closes. Mouths and tongues all over each others’ lips, neck, ears. Fingers nimbly removing articles of clothing to make room for trailing kisses down her body.
She’s naked and I’m in my boxers. I grab her by the ass, lift her, and lay her across my bed. I let my tongue trail across her chest, sucking each nipple before making my way down between her legs. She has quite a large clit that sticks out when she’s aroused and it was stuck way out when I got down there. She had shaved between her legs, leaving a thick but trim landing strip. I still remembered exactly how she liked it. I held her legs back with my forearms and teased along the edges of her lips with my fingers. I licked between her lips into her opening where she was gushing wet. I teased for a little bit before spreading her lips with my fingers and gently flicking her clit with my tongue. Her whole body jerked with the contact and I had to remind her to keep quiet.
I continued circling her clit with my tongue, gradually applying more pressure, then sucking on it and sliding a finger inside her when I knew she was close. She gripped my hair, pulling me into her, saying she was cumming. I could feel her pussy spasm on my finger. She kept pulling my head and I realized she was pulling me up. I slid up from between her legs, having already removed my boxers. I knelt on the edge of the bed and started rubbing my cock between her lips.
“Is this what you want?” She nodded. “I want to hear you say it. What do you want?”
“I want your cock inside me. I want you to fuck me,” she whispered through her pants.
I pressed my head barely inside her. She was incredibly tight. I crawled onto the bed on top of her; her arms and legs wrapped around me, pulling me all the way inside her. The sensation took both of our breaths. She had mentioned her ex was average but she remembered me being bigger. She never used toys, so this was the deepest she had ever been penetrated. I had never stopped lusting for her, so this was an incredible fantasy come true for me.
We just held each other for a bit before I started sliding in and out of her. She rolled her hips back, pulling her legs further up my back. Eventually, I took the hint and held them up for her. As soon as I did, it must’ve hit a good spot and her body began jerking again as she had her first ever orgasm from sex.
We kept fucking, hard. She had several more orgasms while I dripped sweat onto her.
“Do me from behind; it’s my favorite and I want to cum that way, too!”
I pulled out and rolled her over. The sight of her tight little ass up in the air with her pussy splayed out underneath was nearly enough for me to finish right then. I rubbed my cock along her slit, finding the entrance and shoving back in. She’s the absolute perfect height for me to fuck doggy style. I didn’t have to bend over or adjust my angle at all. I held her hips and she braced against the wall, burying her face in my pillow while I fucked her as hard as I could. She came several more times and started having trouble keeping her back arched. I slowed down and she rolled back onto her back.
I’d like to say that I’m just this amazing lover who was able to hold out indefinitely to please this girl. However, the truth is that I couldn’t shake the concern that my mom was going to hear her moans and ruin the whole thing. That little anxiety kept me from ever even approaching my orgasm.
“I’m sorry,” I said. “You’re absolutely incredible but I’m having a hard time finishing like that.”
“Ok, what’s your favorite? Let’s do that for a while so you can cum for me.”
“No, it’s ok. This has been incredible but I’ve been trying to cum for a while. It’s just not gonna happen for me tonight.”
I laid down beside her and we started to kiss some more. She pressed my chest and had me roll onto my back, stroking my cock again.
“Let’s try this, just in case.” She slid down and took my cock into her mouth. Absolute heaven. She held the base of my cock steady with one hand and used her finger and thumb of the other hand to follow her lips as she stroked up and down my entire length. I had jacked off countless times in the year and a half prior thinking about how this would feel. Able to relax and not worry about her waking my mom, my mind let me fully enjoy the pleasure she was giving me.
“Oh God, that feels so good! If you keep doing that, I’m going to cum.”
She kept sucking, same speed. Her tongue pressed flat, sliding up and down across my shaft and head.
“I’m close….that’s, that’s it… I’m cumming!” I tried to give her as much warning as I could, knowing that she hated the idea of tasting cum. She never missed a beat. I felt my first shot erupt and could feel my head swell against her tongue. She squeezed and sucked her lips tight around me, continuing to slide up and down, never changing her pace. Her mouth was so small, I expected her to gag or to feel her release my load but she never did. She held suction and stroked me as I continued to pulse wave after wave of my cum into her. As I started to come down, she slowed her pace. Her fingers stretched further down each stroke now while her mouth stayed around my head. She squeezed my cock firmly on each slow stroke, pulling the last drops of cum out. When she was satisfied that I was empty, I felt her swallow and lick my tip again as she let me fall from her lips.
We dated for a while after that and had some pretty awesome sexy times. I’ll probably share another story or two with her, but that one is by far the best memory I have with her.
Source: reddit.com/r/gonewildstories/comments/5dbi05/prudish_ex_is_a_lot_more_fun_on_our_second_first