Learning About My Girlfriend’s Past short sex stories

To make it even more fun: based on a true story!

**Chapter 1**

Nicky had short brown hair and a round face, with smiling eyes like two half-moons that always seemed squinted, curved downwards like crescent moons. She had a big, slightly lopsided smile that brightened the room, with dimples and a thin upper lip, but a protruding lower lip that would occasionally tremble if she was upset or anxious. She had an unconventional look, some might say a little plain; I thought she was beautiful. She had smooth skin, tanner than mine – she was a swimmer and kept herself fit, hiking spring through fall, and swimming outdoors in the summer. She was tall, about 5’10”.

I’m 6’3” myself, thin with broad shoulders and short, dirty blond hair. When we met, I was a bit out of shape, but she got me into swimming and eventually I got fit as well. Not as fit as her, but at least I lost some of the pudge.

About four months into our relationship, I got up the courage to suggest we share kinks and fantasies in a no-judgement space. I was certain even then that neither of us would reveal everything, but hoped it might spice things up. Our sex life at that point was very good, but vanilla. My idea was to find a list of kinks online and have us independently fill out things we would like to do, things we would like to explore purely as a fantasy, things we were OK with trying but weren’t particularly interested in, and things we didn’t want to do.

We learned a lot from that. I was at least OK with most things; she was a bit more reserved. I learned something I already more-or-less knew, which was that she very much liked being dominated. She liked some light BDSM – in particular, she was interested in wearing a collar and a leash, which sounded like a lot of fun to me. That already was enough to start spicing up our sex life.

I was timid in revealing my main kink, which was some variation on cuckolding. I wouldn’t say outright cuckolding, but the idea of Nicky with another man – or men – was a huge turn on. I presented it as purely fantasy, something I wanted to roleplay in the bedroom but didn’t want to do in real life.

She seemed a little taken aback by it but handled it well, and was open to exploring it as a fantasy. Over time we did two things: first, we began to talk about some of her past sexual experiences, and second, we roleplayed in the bedroom. Over time, she got into it and the fantasies became more common and more elaborate. I bought her a realistic dildo, much larger than myself, and we pretended it was her “other boyfriend.” We had fun with it. Sometimes she would text me, pretending she was going to see her “lover.” Occasionally she’d take a cleverly framed picture with the dildo and we’d pretend it was real. She’d fuck herself with it and then come over to my place, telling me all the naughty things she’d done before I’d “reclaim” her for myself.

One of the key rules was that her lover needed to be meaningfully different than me. A different age – older or younger. Or a different race, or body type. Sometimes we’d play around with the options, but she seemed most drawn towards pretending her boyfriend was an older man. It was a turn on for both of us. Eventually things became more specific, and we began to flesh out entire characters. We incorporated impregnation fantasies in our play as well, having pretend risky sex with her fake lover. I’ll spare the details for now, but may return to them at some point.

When it came to her past experiences, I asked her about older men. She would eventually reveal two that were significantly older, but neither quite as old as our fantasy character. In her early twenties, she had a boyfriend who was nearly forty five for about a year, and even moved in with him for several months. She regretted it deeply from a life perspective, but was fuel for a lot of our fantasy. Outside of that, she’d only had one other experience, when she’d been horny and met a man around the same age through a dating app and had sex with him a handful of times.

She met her husband after that. They began dating when she was 23, and were divorced by the time she was 25. It was a short marriage, and not a particularly good one. I was the next person she dated after that, two years later. Outside of the already mentioned, she’d had some odds and ends experiences, mostly in high school, but nothing lasting longer than a couple of months. Two hookups – a one night stand, one time with a friend.

After about a month or so experimenting with these fantasies, we were both in bed, wine drunk and fooling around a bit, and I asked, “So is there anyone from your past you haven’t told me about?”

She hesitated a bit. “Maybe a few, but just ones I don’t think you’d find interesting.”

“Babe, I’d find any of it interesting,” I smiled over at her as I stroked her lower chest.

She hesitated again. “Well I think it would be weird. What if it was someone you might run into? You wouldn’t want to know about that, would you?”

I let out a small chuckle. “I’d probably just find that hotter.”

“Really? I feel like that would just be weird.”

“You can tell me anything, it’s just the past. And this is a safe space, remember?”

“What if it’s someone I still run into in my everyday life?”

I paused for a bit. “That’s okay. Like a coworker or something?”

“No…” she sighed a bit. “You promise it won’t be weird?” she said, slurring her words a little bit.

“I promise. We can have fun with it,” I said, caressing her stomach.

There was a long silence. “I had sex with my neighbor.”

I knew immediately which neighbor she meant. She lived in a townhouse that she’d recently bought from her parents, and before that had rented it since a bit before her marriage. One side was a lesbian couple. The other was a much older man, I guessed around 55, although I’d find out later he was 61 at the time. He was a Serbian immigrant, his accent faded but still present, he had a gruff voice. His dark brown hair was by now mostly gray, and he had a large frame, muscular but chubby, very hairy with a medium length beard. He was shorter than her, about 5’8”, but still very large next to her. I’d only actually seen him a few times, given that we spent much more time at my house. Immediately my mind reeled with images of him fucking her. Maybe I’d asked too much. Maybe I wasn’t okay with this.

“Oh wow, Luka?” I said after another pregnant pause, a bit shocked, my hand now coming to rest against her belly.

We’d talked about him on occasion – his wife had died of cancer a couple years ago, right around the time of her divorce. In the summers, she’d plant flowers in his garden, like his wife had done. It had always struck me as a very sweet thing for her to do. A picture started to form of how this might have happened.

“Fuck,” she said. “I can’t believe I told you that.” Her face sunk, and her head slumped forward a bit. “Fuck fuck fuck. Can we just forget about it? I’m so sorry.” She got up, walking quickly towards the bathroom.

“No, no,” I said, collecting myself. “Babe it’s okay, I’m glad you told me about it,” I said as she slammed the door behind herself and locked it. *Shit*, I thought to myself. I shouldn’t have pushed her on this one, she clearly didn’t want to tell me. I should’ve reacted better.

I got up and approached the door. I could hear her crying inside. Knocking, I repeated, “Babe, it’s okay, it’s nothing to be ashamed of.”

“Yes it is,” I heard her sobbing back at me. “I’m so disgusting.”

“No you’re not,” I said. “It’s just sex. There’s nothing wrong with you.”

I slumped down, sitting there on the ground with my back against the door as she remained inside. We talked back and forth a bit until she calmed down a few minutes later. Eventually I heard the click of the lock. Scrambling to my feet, I met her with a hug as she emerged, face red and disheveled from crying.

“I’m so embarrassed,” she said.

“Shh,” I said as I kissed her on the forehead. “There’s nothing to be embarrassed about, really.” I held her tightly.

“You probably think I’m disgusting.”

“Not at all,” I said. “Why would I? Is it that much different than some of the other guys you told me about?”

After a few seconds, she let out in kind of a whimper, “I guess not.”

“It’s really not.”

“Isn’t it weird that you’ve seen him? That he still lives next door?”

“I mean,” I tried to choose my words carefully, “I guess it’s a little weird, but it really doesn’t bother me, it’s okay.”

She looked up at me, fresh tears still running down her face. “You promise?”

“Of course, I said,” leaning over to kiss her lips. “I love you. Why don’t we get you a little more wine?”

She finally cracked a smile. “Okay, I need a drink,” she laughed, breaking the tense mood.

Down in the kitchen, her spirits had begun to rise a bit. We poured wine and talked about other things for a bit. Eventually I just blurted out, “Honestly, the neighbor thing is kind of hot.”

“Really?” she looked at me warily.

“Yeah. I mean, if you don’t want to talk about it anymore that’s okay, but it’d be fun to hear about.”

“I dunno…” she trailed off. “You really want to hear about that? Wouldn’t that just be weird next time you see him?”

“I mean, it’ll already be a little weird but it’s okay. You know I like hearing about it. Like I said, is it really that much different than the other ones?”

“I guess not,” she said, by now a little drunker. A mischievous smile grew across her face. I walked over and kissed her deeply, running my hand down her body, I slipped it into the front of her panties and slowly rubbed as we kissed.

“Let’s go sit on the couch and you can tell me about it,” I said. We sat down, setting our wine glasses on the coffee table, and I reached over to touch her again, slowly and gently, as I whispered in her ear, “So how did it happen?”

She opened up, telling me how she started spending a lot of time with him since he had just lost his wife and she was newly divorced. She’d bring him dinner, help him with his garden, and sometimes they’d just talk. So it started very innocently, two temporarily broken people connecting as humans after difficult losses.

Occasionally there’d be a little flirtation. Over time that grew a bit, until there was sexual tension. Eventually one night they were sitting together after dinner, watching the neighborhood pass by as the sun set. It grew dark, and the lights were out on the porch. They continued to chat the evening away, and at some point he rested his hand on her thigh. They sat there for a bit silently, still watching the street, and she laid her hand on his. After a bit, they clasped their hands together. They looked over at each other and smiled nervously, then looked back ahead. After a bit more time passed, he looked back over at her. “Thank you so much for your kindness,” he said in his Serbian accent. “It means so much to me.”

She smiled at him, and this time they locked eyes much longer, their faces only inches apart. She leaned in, and they kissed. Hungrily. The tension broken, both longing the touch of another person, they kissed deeply and passionately, his meaty tongue poking into her mouth. She felt disbelief at what was happening. She knew it was a terrible idea. She knew she should stop it. But she didn’t. His hands began to roam across her body, running up and down her back, her thighs, her sides. Eventually one of his big mitts grasped her ass, and as he pulled her into him, she climbed onto his lap. He kissed her neck and grabbed her breast with his other hand. She could feel his erection pressing against her, and in a moment of boldness, reached down to touch it through his khaki pants. He reached his hand up under her shirt, under her bra, and continued to fondle her breast as he slipped the hand on her ass down the back of her pants.

“Maybe we should go inside,” she panted in his ear, becoming suddenly aware that even in the darkness, there was a small chance they might be seen. Neighbors could not know about this.

She followed him inside with second thoughts. She almost stopped herself, almost said *wait, this is a mistake*, but she swallowed the words. He grabbed her hand as they reached the door and led her into the living room. Once inside, he turned back around and began to kiss her again, his hands again exploring her young body, her hands wrapped behind his back.

She pulled back for a moment. “Sit down on the couch,” she said. She pulled off her shirt, then her bra, and leaned over to unbuckle his belt, undo his button, and unzip his pants. As she did so, he reached out to grab one of her hanging breasts. She pulled down the front of his pants, allowing his cock to spring out. As she described it, it was fairly large. About the length of mine, she said, but thick. He was uncircumcised and untrimmed, a thick beard surrounding it, making it look a bit smaller than it really was.

Pushing the coffee table back, she knelt down and took it in her mouth, feeling it throb against her tongue. Slowly, she sucked on it, working it deeper into her mouth little by little. Occasionally she would pop it out of her mouth and run her tongue along the shaft. She had always been proud of her oral skills.

She asked him to pull his pants down a bit further, and he did, briefly hopping up off the couch as he pulled them down another half foot, revealing himself more fully. She leaned in and took one of his large, swollen balls in her mouth. She wasn’t used to the amount of hair, but she sucked on them nonetheless. Then she’d glide her tongue back to the tip, perhaps tasting the salty precum that had accumulated, and began to suck again. As it went on like this, he’d occasionally run his hands over her, grab her tits, or grab her hair lightly. When it would fall in her face, he’d tenderly sweep it aside.

After a while, she stood back on her feet, kicking off her shoes and slipping off her leggings and panties, now naked except for her socks. She told him to lean back. As she had on the porch, she climbed onto his lap. Reaching down, she grabbed his cock and began to ease it inside herself, drawing a sharp breath. “Don’t worry,” she said breathlessly, “I’m on birth control.”

By now she was quite wet, but it still took a bit to work him inside her, going up and down and slowly lubricating it as she inched further. He was the widest she’d experienced, and the stretch, the fullness, felt amazing inside of her. Eventually she eased herself down to the base, the tip pressing firmly against her cervix, an exquisite mix of slight pain and pleasure. She sat like that for a moment, leaning in to kiss him again as he fondled her body. Having been married for decades, he hadn’t felt such young, firm, soft skin in ages.

At this point in the story, my fingers are slipping in and out of her. She was soaking wet and loose with arousal. I had to restrain myself from fucking her right there. I needed to hear the rest. I should mention that the details herein aren’t all exactly as she told me that night. Some are details my overactive imagination has filled in. Others I’d learn as we revisited this encounter again and again. I encouraged her as she told it, slurring her words and breathing heavily as I touched her. Occasionally I’d whisper something in her ear, letting her know how much I enjoyed the story, helping relieve her anxiety. Still, there was some hesitation as she talked through it.

As they kissed, she began to slowly slide up and down on him, her ass bouncing against his thighs as his stomach pressed against her body. Their hands and mouths explored each other’s body and the pace eventually quickened. Before she knew it, an orgasm began to wash over her. She came hard, letting out a high pitched gasp and pushing him out of her, and leaning forward onto his body, trembling there for ten, twenty seconds as she panted. He smacked her ass and she let out a little grunt.

This detail surprised me a bit, as she had trouble orgasming from sex and usually needed specific positions and a lot of work. Of course, she was sex starved and extremely worked up, so perhaps it wasn’t too unusual. Still, I felt a bit of a pang in my chest.

She lay there on top of him for a bit, collecting her breath. “Here, get up,” he said. Standing up behind her, he placed his hands on her hips and positioned her next to the couch, pushing against her upper back to bend her forward. He pulled off his shirt and his pants fell to his ankles. Fumbling a bit with his hand from behind, perhaps a bit out of practice, he slid back into her with ease. She drew a sharp breath, muttering “that feels good.”

He began to thrust with long, firm strokes, his thick cock stretching her in different parts as it slid through. His hands were planted firmly on her hips, and he would push her forward a bit as he pulled back, then pull her in as he pushed forward, his belly pressing against her ass as she leaned forward on her elbows. Keeping a steady, slow rhythm, he suddenly smacked her ass hard. She let out a little yelp, and a giggle. “Mmm,” she let out a little sound to tell him she liked it. They kept like this for a bit, him occasionally smacking her ass, occasionally squeezing it and running one hand along her back.

She turned her head a bit back towards him and said “fuck me harder,” with a sly grin. He caught her off guard once more by gathering her hair in one hand and pulling it as he began to pound harder and faster. She slipped forward onto her chest, her face pushing further and further into the edge of the couch as he fucked her. It hurt some, but she didn’t stop him. It didn’t take long like this before she felt him tense up, coming to a stop deep inside her. She felt the warmth of him spurting inside her as he let out a guttural groan. His cock pulsed and throbbed inside. They sat there motionless for a while until he withdrew from her, both inhaling sharply as he did.

His cum immediately began to flood out of her, dripping down along the front of the couch and against her thigh. He plopped down a couple feet from her, panting heavily, and after a few moments her butt fell over sideways into him. Planting his hand on her ass once more, he slid his fingers against her, tracing up and down her slit, wet with her cum and his. She sat up and leaned onto him, her head resting against his sweaty, hairy chest and her hands on his thigh. He reached around the side of her and they cuddled there a while.

“That was good,” she whispered. He patted her thigh.

“For me too,” he said after a moment.

It was at this point that I looked over at her and said, “Do you want to fuck me like that?”

She grinned. “Yeah, let’s do it.”

I insisted we put on some more clothes before leading her downstairs to the couch. We began to play it out, detail by detail. I must say, some things were different. When she sat down on me, I slipped in with relative ease, she was so turned on. And likewise, I didn’t last as long as he did, cumming fairly quickly as she rode me.

“Aw, I didn’t get to the best part,” I chuckled. She leaned over and kissed me.

“That’s okay, we can do it again,” she smiled.

We went upstairs, undressed, and crawled into bed, drifting off to sleep as I held her in my arms.

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