This happened a few years ago. Back before Tinder, there was a website that’s moniker was “life is short, have an affair”, before the huge data breach that revealed all of its accounts…
I had an account, paid membership all of that stuff. I was looking for some on the side for my own reasons. I was in Chicago for an almost month long school for work. While I was there I thought I would try that area on that site, the class was in a northern suburb. I set my search area to see who was out there. I sent a couple of messages and within a couple days had a response. We chatted a little back and forth and she gave me access to all of her profile pictures. She was a few years younger than me, on the shorter side, with a little shorter than shoulder length brown hair, cut in a way that went well with her cute round face. She wasn’t skinny, but not overweight either, she was thick in all the right places. A few questions led me to find out that she’s a roller derby girl, that in itself was hot. Her body showed her athleticism, her calves, thighs and butt showed of years of skating, but what overwhelmingly stood out was her enormous breasts, they were also very prominent in her pictures, she did like to show them off! I asked, she said they were 36H cup. We chatted for a few days and decided that we should meet. We decided on a public park between my hotel and where she worked.
The afternoon arrived and I drove to the park. I arrived first, and was nervous as there were other people at the park too. Not wanting to be weird and just sit in my car, I went to a gazebo and sat at a bench. She messaged me when she arrived and I told her where I was. She got out of her car and walked towards me. She was wearing jeans and a nice top, having come straight from work, even as she walked towards me I noticed how short she actually was, around 5’3″, and how huge her breasts really were, the top she had on struggling to contain them. I stood to meet her and towered over her at my height of 6’2″. I’m not a big guy at around 195lbs, I’ve got a runners build, as I do run often. We exchanged quick hello’s and decided that we should walk around the outer loop of the park. Our walk quickly turns flirty as our discussion leads from both of our work to why we were both on that site. At one point our hands bump as we’re walking and we end up holding hands as we walk. As we round a corner, I notice that no one is around and I take the opportunity to be the aggressor, I place my arm around her waist, spin her around and back her up against a tree next to the path. I lean down and kiss her, she kisses me back, and we are quickly making out against the tree. I push my weight into her, pinning her against the tree as our kissing begins to heat up. Before long my hands are feeling up her breasts over her shirt and bra, and she in turn puts her hand over my hardening I cock in my short.
The noise from other people catch our attention and we break from our improv make out session. We continue our walk around the loop back to the gazebo we met at. Once there we sit down, still holding hands and occasionally kissing in between whatever we’re talking about. She now takes the chance to be the aggressor, and tells me she’s going to blow me right there on the bench. I scoff and tell her there’s too many people around. She calls my bluff and starts to undo the button and zipper of the shorts I’m wearing. She has her hand in my pants now, rubbing my rapidly rehardening erection. She pulls at my waistband and slides my shorts and boxers down enough for my cock to get free. I’m not huge, but I’ve been told before that I’m well above average, she seems to like what she sees anyway, and before I can protest, her head is in my lap, and my now very hard cock is in her mouth. In an attempt to not let anyone see what she’s up to, she scoots herself closer to me, and with one hand on the base of my cock, she takes most of me in to her mouth. She’s good too, using only her mouth and throat she’s quickly getting metowards the point of no return. I try to distract myself from the quickly building urge to cum, first by reaching between her legs to rub her pussy over her jeans, but the way we’re seated makes that an almost impossible angle, then I try to get a hand in her shirt. She mumbles no without taking her lips from my cock, so I lace my fingers through her hair and gently pull her away from my cock. Her face is pouty and questioning as I look in to her eyes and tell her that I was about to cum. “That’s the point”, she whimsically replies. And, before I can fully process what she’s just said, she drops her head back into my lap. Her warm, wet lips and mouth soon surround my aching cock again. God she’s good at it, her hand never leaving the base of my cock, holding it in position while she sucks and swirls her tongue around my cock while she bobs up and down on it. I’m sure there were a couple “Oh my god’s” muttered, and very quickly, I mutter that I’m going to cum. Undeterred, she doesn’t hesitate to continue at her current pace. I feel my balls tighten and the initial rush as I start to cum. She in turn pushes my cock further in to her mouth as I start pumping shot after shot of cum into her mouth, her suction around my shaft is secure and she swallows every drop, letting none of it escape. A few more seconds of sucking to make sure she got it all, until I start to squirm a little, the overload of sensations making my cock super sensitive. She releases my cock, and sits up with a smile on her face. I, un-stealthily sit up slightly and stuff my softening cock back in to my boxers and shorts, being careful not to get anything accidentally stuck in the zipper.
I lean in to kiss her. “You just came in my mouth” she says, “it’s not like it’s someone else’s” I replied. Later she told me how hot she thought that was. The kiss is good, but a little reserved because I’m not that in to tasting my own cum. She said that she needed to get going, her husband was at home… I tell her good, we should get together again, soon. She agreed and said she’d message me.
We chat for about week about all of the naughty things we want to do to each other and she finally figures out a day, and a solid excuse, to come to my hotel room after work. I’m excited, and honestly a tad nervous the afternoon that she’s supposed to come over. I clean up all of the shit I’ve just left wherever in the hotel room, run to the store for condoms and some drinks, get back and get in the shower, you know, to smell good.
She finally messages and says she’s there. I go to the lobby to pick her up. We smile and greet each other. And we walk hand in hand through the hotel to the elevator and up to my room. We get back to the room, it’s a standard 2 queen with a kitchenette suite. She asks where to go, I motion to the bed I hadn’t been sleeping in. I turn on the TV and join her on the bed. We chat and watch whatever is on TV, and start to snuggle and explore each others bodies. This is when she tells me that her breasts are more than big enough to be used as pillows. I accept the invite and lay my head on her right breast and start messaging the other. She was right, it was heavenly laying my head on her big soft breast while she scratched my head. I turn my head towards hers and we kiss, which quickly escalates to full on making out, our tongues aggressively exploring each others mouths and tongues, and our hands roaming to wherever they can reach. I don’t remember who started removing the others clothes first, but soon we were down to just me in my boxer briefs and socks, and her in just her bra and panties. She’s laying on her back, and I’m laying half on top of her, “I need to see your tits”, I tell her. She giggles and tells me that she’ll take off her bra, it’s not the simplest thing to get off. She sits up, and does that thing that only a woman knows how to do where she unclasp’s and removes the shoulder straps without the cups falling off her breasts. I’m sure my eyes were huge and my mouth was agape while I waited anxiously like a kid unwrapping a Christmas present. Finally she pinches the connecting piece of material in the middle and slowly pulls her bra off. “Holy shit” I said aloud, “those are huge”. “Yup” she replies, a devilish grin on her face. Huge isn’t an adequate enough description. They were almost the same size as her head, full, and round, boobs that big aren’t pert, but hers didn’t have the standard huge boob sag either. Her areola are large and round, and a dark pinkish/brown, with large stiff nipples perfectly centered on each. I lean in and kiss her deeply, my hands drawn to them. They were way to big for one hand, that didn’t stop me from cupping and massaging each one, while occasionally rolling her thick nipples between my thumbs and forefingers. I push her back to laying down and I work my way from her mouth, to her neck, and collarbone and then on to her breasts again. I licked, kissed and sucked on them for a good 5 minutes, they were and still are the biggest set of tits I’ve ever gotten to enjoy. I continue kissing down to her naval and beyond. Quickly finding my way to her panty covered pussy. I could see a wet spot in the fabric, and could smell her womanly aroma. I needed to taste her. Not wasting time, I slide her panties to one side and lightly lick her thighs and then her smooth outer lips. She tasted good, and her moans made me believe she was enjoying what I was doing. I continue to lick her outer lips from bottom to top with her panties pulled to the side, until she lifts her hips from bed and pushes her panties down as far as she can. I take the hint and pause what I’m doing long enough to get them off both of her legs. As soon as they’re off and on the floor, I dive right back in to her sweet, wet shaved innie. I focus the attention of my tongue on her clit, as I start rubbing her entrance with my index finger. I insert one, then two fingers inside of her very wet pussy while I continue to suck and lick at her clit. I take a third finger and press it against her asshole and I hear and feel her have a small orgasm. She pushes my head away from her pussy, taking the hint I remove my fingers from her too. “I need to fuck you” she says. “Not until I do something first” I tell her. I stand up, take my boxer briefs and socks off, my hard cock pops out standing at full attention and I climb on to the bed and on top of her until I’m semi seated on her, my cock directly between her huge tits. She knows what I want, and she pushes her breasts together until they envelop my cock. She picks her head up off the bed and takes the head of my cock in her mouth. “We need a little lube”, she says taking my cock from her mouth momentarily. After just a minute or so she says “that’s better”. Again she puts her hands on the outside of her breasts and pushes them together around my cock. I start pumping my dick back and forth in her ample cleavage, it’s my first time getting to titty fuck a woman, and it’s better than I imagined. The softness of the skin of her breasts is a new and exciting feeling. I reach back with my right hand and start rubbing her clit again while my dick continues to slide back and forth between her breasts. They’re so big that my cock completely disappears between them, only the head reappears as I stroke back and forth. Once or twice she lifts her head up and takes the head of my cock in her mouth when I push forward. After a few minutes of this, she tells me “I need to fuck you now”, well who am I to argue?
“Lay down” she says, so I roll off of her on to my back on the bed. She in turn is up on her knees and straddling me immediately. She slides up my waist so that she has my cock pinned between her pussy and my abdomen and is grinding back and forth on it, rubbing my cock against her clit. Her knees are on the bed, and she’s seated upright, still grinding back and forth. Teasing both of us as she uses my cock to stimulate her clit. “Condom”, she says. I point to package of them on the nightstand beside my head. She reaches over me for the package and gets one out, she tears it open quickly, and rolls it on to my erect cock. Once the condom is on, she lifts herself up and positions the head at her opening. Slowly she lowers herself on to me and holy shit is she tight. She’s more than wet and ready, however it takes several slow and steady times for her pussy to accommodate me. One final time she lifts herself up and I slide all the way in, and she settles herself down with me completely inside of her. Instead of bouncing up and down, or laying on top of me, she instead begins to slowly grind herself on me. I can feel her pushing her clit into my pelvic bone as she grinds back and forth still seated upright. I reach up and play with her glorious beasts. This is the first opportunity for me to grasp how heavy they are are. I need two hands to feel each one. I figure our she likes having each of my hands on each of her beasts, kneading and pinching each one at the same time. Her nipples are rock hard and her areola tighten up and have the wonderful bumps on them when her nipples are hard. I sit up and take one then the other nipple in my mouth, sucking and slightly nibbling on each in turn. She continued to rock back and forth on my cock, using the stimulation to her clit to help drive her to her next orgasm. Which doesn’t take long with all of the added stimulation I’m giving her breasts. Soon her breathing quickens and her moans become like little gasps. “Oh god” she exclaims, and leans over me, her massive tits smashing into my chest, I wrap my arms around her and start pumping in and out of her as fast as I can. I feel her pussy tighten around my cock and her body starts quivering as her orgasm hits. I slow down and eventually stop thrusting as her orgasm subsides and she fully collapses on top of me. We lay there together, my cock still inside of her as she recovers from her orgasm. She finally picks her head up, kisses me lightly and asks if I got to. I tell her no, that it was okay. That was for the time on the bench.
She smiles and asks me “how do you want to cum?”. I think about it for a moment, and I tell her that I want to cum on her tits. “Oh yeah? How?” she asks. I tell her that I want to sit on the bed and have her kneel in front of my while I fuck her breasts. She gets up, tells me to take off the condom as she grabs a pillow and throws it on the floor. I swing my legs off the bed and she puts the pillow between my legs on the floor. She kneels upright on the pillow between my legs. Licks the palm of her hand and then smears it between her breasts for lube. She then wraps her breasts around my cock and squeezes ever so slightly. With my cock between her breasts she starts to fuck me with them. The warm, soft skin of her breasts, and the just right amount of pressure she has applied by squeezing them together feels phenomenal. Never breaking eye contact with me, she continues up and down on my cock. The feeling of my cock buried between her huge tits is something I will never forget.
She stares up at me with my cock between her tits, bobbing up and down, up and down, her pace was fast but not frantic. She definitely knew what she was doing. I finally start to feel my orgasm building. I grab hold of the edge of the bed and start thrusting my hips in rhythm with the tempo she’s set. I tell her I’m going to cum only seconds before, and when I do, it’s the biggest load of cum ever. The first shot hits the bottom of her chin, and then there is shot after shot after shot of it. I had to have spurted 7 times, covering her entire chest. I take my hand and put it around the back of her head and guide it towards my softening cock. She leans in and sucks out the last couple of drops, and finally looks down at the amount of cum I’ve left on her. “Cleanup, isle me” she exclaims giggling. We both laugh and she gets up to go to the bathroom to clean herself off, and I collapse back on to the bed.
She left not long after that and we never had another chance to meet up. We messaged each other for a while, even tried to set up a get together one other time when I traveled back close to that area, but never did.
Source: reddit.com/r/gonewildstories/comments/d1eatn/my_summer_affair_long