My [M] liaisons with divorced BBW Indian mom [F]

One of the hotter relationships I’ve ever been in was hooking up with an older woman. I had been fantasizing about it for a while, like a porn thing, but decided to give it a shot. Why not. I’m a 25 year old white guy, nothing spectacular, but good enough, I think.

I set up an OKC account and started messaging older women. It was all cold calls, shooting my shot and seeing what happened. Almost nobody responded, and even fewer responded positively. After a while, though, one did respond, asking why I was messaging her and not someone my own age. I was straightforward, and said that I liked the idea of a discreet, no strings attached relationship with an older woman, that there was something hot about being a younger guy getting with an older woman that he isn’t supposed to get with. I ended my explanation with “if you’re feeling bold.” Not my usual style, but this was just messaging online and I figured I could be a bit…bold.

She responded, “I am bold.”

We exchanged numbers and texted for the next week or so. Nothing too salacious, but explaining what I was looking for, and getting more comfortable with each other.

We agreed to meet up at an ice cream shop in her town (a suburb) on Saturday at 8pm. I took an Uber there, and went inside, but it was absolutely packed with teenagers. Not exactly the crowd I wanted to have a first date with someone nearly 20 years older than me. I texted her that we might want to find another place, but she replied that she was just arriving and we’d have to find somewhere, and that I should come out and hop in her car. I joined her, and she drove around the block to a backstreet and parked, and we started chatting. The conversation was really nice. I felt confident, she felt comfortable, and we chitchatted in her car for two hours about just about everything. Our lives, our jobs, her kids, ex-husband, everything.

Inevitably she asked me again why I messaged her, and I told her that the idea of a relationship with an older woman – secret, only ever so often – was really hot to me. It isn’t socially acceptable, but that means it come without longterm relationship implications, so we could have fun and let it just be fun. She invited me back to her house.

She lived on a quiet residential street in a wealthy suburb. Nice – expensive – older home. Her car was nice too, and it was pretty clear that she was upper middle class at least. She said her kids were with her ex-husband, and we sat in the TV room off the kitchen. She cracked a bottle of wine, and I sat in the armchair, while she sat on the couch. We kept chatting, and the conversation felt great. Natural and fun and I felt like a million bucks, feeling like I was wooing this woman who’d normally never think of me in this way, who shouldn’t be talking to me like this, and who’d normally be socially off-limits.

In conventional terms, she wasn’t a model by any means. She was around 5’2″, probably 250lbs, and 43. She was from India, but had come to the US as a kid, and grew up here. She had gotten married when she was quite young, in her early 20s, with an Indian man whose family her parents knew. They had had two children, now 12 and 8, but her husband was a pretty cruel man who had hit her, cheated on her, the works. They had gotten divorced three years prior, and her dad had helped her get back on her feet financially. She said that life was pretty good, but she wanted to get back into the dating scene, and hadn’t had too much luck. She said that my message had excited her, and for most of the same reasons that I had explained: she was supposed to be dating men her age, established men with careers and lives, and to build a longterm relationship. But this wasn’t going as well as she had hoped, and my suggestion of a discreet, no strings attached fling with a younger guy was exciting in the way that something forbidden always is.

I got up from the armchair and sat next to her on the couch. She looked at me with a bit of a smirk, and moved in to kiss her. She giggled and said, “so this is why you came to sit over here.” I said, “yup” and we started making out.

We kissed for a while, and I got a bit handsy, caressing her waist, and eventually her breasts. I took off my collared shirt, wearing a white v-neck. After a bit, I backed off and smirkingly said, “we should head upstairs.” She just nodded her head.

We got up to her bedroom, and the only light was the bathroom light coming through the almost closed door. I quickly took my shirt and pants off, and began kissing her again while pushing her backwards towards the bed. She sat down on it, and I climbed on top of her as she got further back onto the bed, laying down. I started grabbing her boobs, feeling them, squeezing them, and she moaned a bit amidst the heavy breathing. After a bit of this, I grabbed her shoulders, pulled her up so she was sitting, and took off her shirt. She was a bit self-conscious, but nothing a little more kissing couldn’t fix. Eventually I got her out of her leggings, and she laid back on the bed in her bra and panties.

Kneeling on the bed between her anklesI started caressing her legs, especially inside her thighs, and pushed them wider. I started touching her clit through her panties, and she started moaning softly again. I took this as my cue and reached under her ass to grab her panties and pull them down. She wriggled her legs a bit to help, then sat up and took off her bra. Then she laid down again, I was in between her legs, staring at her pussy and boobs. Her belly was a bit big, but I didn’t care. I was about to sleep with a divorced single mom on the first night. Was about to live that porn fantasy, get with a milf, and give her everything only a younger guy could give her. It was naughty, empowering and just very hot.

I started to touch her pussy. First around the edges, massaging her labia, but working upwards towards her clit. When I began softly touching it, she arched her back, and her boobs and belly jiggled a little bit as she spasmed. I started more aggressively massaging her clit, and then put my finger into her pussy. I started fingering her hard. She moaned like crazy, and after a little bit, her arms and legs started to shake, she clenched her things onto my arm, and she yelled, “Oh god, I’m having an orgasm.” Took be aback for second, as I’d never been with someone who used that word instead of “cumming” while they’re in the moment, but it was just way too hot to see this successful, (apparently) wealthy professional woman and mother of two kids shake and shudder like that. As she finished, I told her, “I’m going to fuck you.”

First, she said, “Oh my god, yes,” and I got off the bed to grab the condom out of my wallet that had been there for longer than I’d have liked. As I walked back to the bed, she said – in her disheveled, post-cumming, heavy-breathing state – “I’m very fertile. I’m really fertile right now.” I kind of smirked, and pulled the condom out of the package and said, “well, that’s why I’ve got this.” I put it on, got back onto the bed, got between her legs, spread them, holding one of her ankles, and rubbed my dick on her clit. She started moaning again. I got into better position, and pushed into her. She gasped, and as I got into my rhythm, she started cumming again. A lot. She was so wet, and came at least twice. After this, I turned her over onto her stomach, spread her legs again, and pushed into her from behind. I pushed her legs back together with my knees, and put my knees on the outside of hers, so I was behind and above her. This has become my favorite position, and she seemed to like it too. As I was pounding, I leaned down and whispered in her ear, “when’s the last time you’ve been fucked like this?” Between moans she said, “Never.” I asked, “When’s the last time you’ve had sex?” She responded, “not since my divorce.” I was a little surprised and my pace slowed, and I more seriously asked, “You haven’t had sex since your ex-husband?” and she responded “I haven’t had sex with anyone except my ex-husband.”

I was kind of shocked, but at the same time it turned me on like crazy. Not only was I giving this woman what she deserved, but I was the first man she’d slept with since a really ugly divorce from a really shitty guy. She hadn’t experienced sex except with a guy she grew to hate, and I was the guy who was breaking that wall. It made me feel like the biggest stud ever, giving her that.

After a while, I came, and took the condom off, flushing it. I laid back on the bed, tired, breathing hard. She was already asleep, and I pretty quickly joined her.

Around 3am or so, I woke up again. Gathered my bearings, looked over, smirked, and began massaging her shoulder. She woke up pretty quickly and smiled. I began touching her back, and ultimately her ass, and when she seemed receptive, and moved back into that position above and behind her. I snapped to, though, realizing I didn’t have another condom, and told her. She was disappointed, didn’t really know what to do, and then I told her that I’ll pull out. She agreed, and I spread her legs and pushed into her again.

It felt absolutely incredible, fucking her without the condom on. Not my smartest or most responsible move, but we’re never our smartest or most responsible when we’re looking at a naked woman.

She came a few times, yelling loudly, loudly enough I thought the neighbors might hear. But I kept going. It was way too hot not too. After maybe ten minutes, she blurted out, almost grunting, “cum in me.” I didn’t even know what to say, really. She had said a couple of times, “I’m very fertile right now,” we had just met that night, and here she was asking me to cum in her. Again, not my most responsible move, but I leaned down to her ear while humping and said, “You want me to cum in you?” She replied, “Oh god, yesss” and this just turned on every wildly irresponsible neuron in my brain. I said, “You aren’t on birth control, are you?” “No.” “You want me to cum in your fertile pussy?” “Yes” “Say it.” “Cum in my fertile pussy.”

The dirty talk all sounds absurd in hindsight, like some bad script, but in the moment that kind of blunt lust was the hottest fucking thing on the planet.

“You want me to pump your fertile pussy full of my young, potent sperm?” “Yes, oh god, yes.” “Say it.” “Fill my fertile pussy with your young potent sperm.” After a bit longer of this back and forth, I obliged. Probably the best orgasm of my life. I pushed deep and clenched until everything I could get out of my dick was in her. I pulled out, fell onto my bad, exhausted, and she fell asleep immediately.

We woke up around 7 or 8, and the same thing happened, just with less talking. Pushed into her, finished in her, and fell back onto my back. We didn’t really talk about having unprotected sex, but just chatted over breakfast. Around 1pm, she drove me back to my apartment in the city, we kissed, and she drove off.

She texted me the next week and asked if I wanted to come over again. Naturally I agreed, and almost immediately upon entering, she blurted out that she had gone to the doctor, gotten tested and got on birth control. We never used a condom after this.

We kept this up for a couple years, meeting up every few weeks. We both dated, and paused seeing each other if things got physical with whoever else we were dating. Once those ended, we started seeing each other again, and the cycle continued.

She’s a wonderful person, and it’s sad not to have those fun weekend romps, but we’ve both moved on now. Last time we talked on the phone, she said I had awakened her sex drive, and she had been with around 30 guys since me. She told me that I was the only one who satisfied her like that. I was the younger guy who showed a divorced mom entering middle age how fun sex could be, and did it in the hottest, most intimate way within four hours of meeting her.

Still feel like I’m ten feet tall when I think about it.

Source: reddit.com/r/gonewildstories/comments/tx1ks3/my_m_liaisons_with_divorced_bbw_indian_mom_f