[MF][Cheating] Destroying my engagement with Molly

Hello again GWS! All of the positive feedback I got after submitting for the first time here last week has me all excited to share again. I don’t have a *ton* of sexcapades that are actually worth sharing, but I have been around the block a few times and would love to share as many as possible! It was kind of a toss-up whether I share what happened when I ran [into Staci](https://www.reddit.com/r/gonewildstories/comments/602lrg/mf_staci_gave_me_the_best_going_away_present) again, or a story about how I was an idiot in my early twenties, cheated on my fiancé with a stripper, and ruined my engagement. A change of pace is always good, so I’m gonna roll with the stripper story this time around. This happened many years ago, and it’s *still* difficult not to beat myself up over how much of an idiot I was when I think back on it. Oh, and apologies if the build-up to actual sexy time is too long here…I kind of can’t help how I write these.
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**Relevant Background**

I got engaged really young. Too young, in fact, to an older woman who trusted me when I guaranteed her that I had no more wild oats to sow. My fiancé was a bartender and worked Friday and Saturday nights, which gave me plenty of nights out with the guys (and probably made me feel like more of a bachelor than I really was).

Every once in a while the stars would align and a night at the strip club would be in the cards. We lived about 45 minutes away from a major city with plenty of joints, but somehow we always ended up at the same place (perhaps because it was one of the only fully-nude clubs that *also* served booze and *also* had a VIP area…perhaps). The only knock against it was that girls couldn’t physically dance **on** you in the VIP area…they could come as close to touching you as possible, but weren’t allowed to give you a true lap dance. Anyways, I don’t know if this is common for other guys, but over time I definitely developed an affinity for one particular dancer there. Her name was Molly, and she was like the LeBron James of stripping. In a sea of dancers full of dead-behind-the-eyes stares, lazy dance moves, and general coked out batshit insanity…Molly was just a woman who loved take her clothes off and dance for a crowd of people. Her enthusiasm is what made her so alluring. Physically, she was obviously attractive, but not in the way that most exotic dancers are. In a valley of silicone, Molly was all natural. She wasn’t anorexic skinny, either; she definitely had a thicker frame. She didn’t cake on her makeup, bedazzle herself, or look like a tattoo artist’s sketch pad either. She was simply a beautiful woman, with long brown hair that fell down to the small of her back, an olive complexion that definitely belied some Italian heritage, and an amazing pearly white smile.

One night, I was tired of the same-old, same-old. Molly was walking the floor, looking for someone who wanted a private dance. I waved her over and asked if they had a couch that was big enough to accommodate getting a dance from two girls at once. She said yes and told me to hang tight. She came back a couple minutes later with another dancer, and they proceeded to do their thing for a couple of songs. It was memorable, hot and fun…but not as enrapturing as I thought it would be for some reason.

**On to the fucking story already**

OK, so fast forward several months. Stars align, and the prospect of a strip club night presents itself. I nearly skipped it, after having found myself not all that satisfied from paying $100 to watch two naked women dance around my lap for 10 minutes the last time I was there. But my friends weren’t going to let me bail, literally showing up at my house and refusing to leave unless I came with. I was so apathetic to the whole thing I didn’t even bother to change in to nice clothes…just left the house in a t-shirt and some basketball shorts.

The night played out much like all the others, except this time I really didn’t engage much. I was hoping to see Molly at least dance up on stage, and after about an hour of nursing a beer I got my wish. Figuring it would be the only time of the night I’d be willing to part with any money, I went up and tipped her a couple of bucks as she danced. She was so in the zone, she barely even noticed my bills being tossed in with the dozens of others from everyone else lining the edge of the stage. A couple of hours later, everyone was off doing their own thing, leaving me alone at our table. From out of nowhere, this chick bounded up to me and jumped onto my lap. Guess who? Molly!

All bubbly personality, Molly wasted no time telling me that she remembered me and glad I was back. I laughed and told her that she much use that line on everyone. She gave a girly little giggle, but told me she did actually remember me because of how tall I am. Now, I am 6’8” (a little over 2 meters for you metric folks), and get this kind of shit *all the time*. Like, to the point where it is annoying to discuss my height in *any* context, woman in my lap or not. Rather than have to answer the usual barrage of questions (yes, I play basketball…yes, everyone asks me about how tall I am, etc) associated with my height, I awkwardly laughed it off and asked if I’d be able to get a dance from her at some point.

I wasn’t expecting what she did next. She leaned in real close to my ear, and said “Actually, I’d like to give you my number.” The look on my face must have given away how surprised I was…despite all of the attention I got for my height, getting hit on by women was not a regular occurrence for me. After she said it, I just kinda froze. Thoughts of my fiancé began to swirl through my head. Thoughts of fucking a stripper started to overlap those thoughts. I really didn’t know what to do. I must have been silent for too long, because she broke the tension by telling me that it was OK if I didn’t want to give it to her. In a move that I will forever remember as possibly the most un-smooth thing I’ve ever done, I raised my right hand (wrong hand, idiot) and pointed to my finger (with no ring on it yet). The look of confusion on her face was so comical that I actually laughed out loud, which brought me back to Earth a bit. I ended up managing to tell her like a normal human being that I was engaged. She didn’t seem all that disappointed, really, and the moment passed quickly. She got up to leave, but I grabbed her wrist and told her I still wanted a dance, though. Dumbass…

Molly, ever the consummate professional, obliged and led me back to the VIP area. Now, what happened next can only be attributed to some kind of odd twist of fate. We’re walking the rows of booths/couches in the VIP, and literally all of them are filled. I’d never seen that happen before, as there were like two dozen of them. Molly tells me to hang tight, and goes and talks to a bouncer for a minute. She comes back all smiles, and tells me that we don’t have to wait for the song to end…that we can go use this club’s equivalent of a “champagne/party room” We weave our way back out of the VIP and down this different hallway. She leads me into an actual *closed off room*, which is just decked to the nines with a mini-bar, couches, poles, etc.
She sat me down on the couch and proceeded to start slowly dancing in front of me. Her body was familiar, but was still a sight to behold. Molly’s rhythm was so impeccable…the way she’d sway her hips could have literally hypnotized me, doing these sexy little dips as she’d rock her hips. She hooked one of her thumbs into the front of the waistband of her underwear, and slowly teased it down, letting me see inch by glorious inch how bare she was. Such a tease, though, as she quickly released her thumb, letting the elastic snap back in to place. I won’t lie, I usually avoided making eye contact with dancers during private sessions…I just couldn’t handle the awkwardness. In this case, though, I chanced a look up at Molly and met her eyes full-on. She was gently biting her bottom lip, her top lip in this sexy pout, which revealed a couple of her perfect white teeth. It was the most seductive look I think I’ve ever been on the receiving end of in my life, and it was in that moment that a thought struck me…what if, when I told Molly I still wanted a dance, I had more or less challenged her to “convince me” to give her my phone number? Danger Will Robinson! Danger!

I had two options: let this continue, or politely try and leave. I still felt like I was in control of the situation…there was no part of me that assumed I would be doing anything that actually constituted cheating inside of that club, closed door notwithstanding. I had also already paid for the dance…so I decided to sit tight and just try to enjoy myself.
Probably clueless to my inner turmoil, Molly proceeded to get completely naked. By the time she had her g-string around her ankles she was facing away from me, legs spread slightly open, gently shaking her ass in my face. The room wasn’t super dark, so I had an amazing view of her from behind. She actually stepped out of her underwear backwards, moving even closer towards me, and slowly reached behind herself and spread her ass open. I could have eaten dinner out of that asshole, it was so clean…just a perfect little knot! She let me admire the view, looking back at me over her shoulder.

For the next couple of minutes, nothing out of the ordinary happened. While Molly was an absolute pro at what she did, there was nothing about her routine that I hadn’t received from her or other dancers dozens of times. The only difference was the eye contact. She barely broke it, always just watching me as my eyes feasted upon her perfect body. Eventually, the song ended and I figured the dance was over. As I stood up to leave I realized that I was rock hard and needed to hide my erection in my waistband. This was a move that I knew was going to be noticed despite how smoothly I would be able to pull it off, but the alternative was to go walk back out pitching a literal tent in my basketball shorts, so I went for it.
Molly saw the whole thing, and smiled seductively at me once I was finished. I grinned sheepishly and shrugged my shoulders, with a “What are ya gonna do?” kind of face on. Then, with no warning, Molly steps close enough to me to kiss me, places her hand on my chest and pushes me back. Very few people can shove me to the point where I would actually fall down, but I guess my body knew to take the hint before my brain registered what was actually going on, as I went down like a straw house. Sitting back on the couch, looking up at this olive-skinned goddess, I felt my cock swell in between my stomach and the waistband of my shorts. Any part of my brain capable of thinking about my fiancé just shut off, as Molly straddled me and began grinding her still-bare pussy all over my lap.

If I thought I was turned on before, this just took it to a whole new level. I’d never really had the pleasure of touching Molly like this before. She wrapped one hand behind my neck, planted the other hand on my knee, and proceeded to grind and bounce all over me, tossing her hair back wildly. I thought my dick was about to blast off. Thinking I was the shit, I would clench my ass as tight as possible, trying to swell my cock up as much as I could when she’d rub that smooth little pussy over top of it. Through just the thin layers of cotton and nylon, I could feel that her snatch was burning up, which only fueled me even more. I was so young and dumb, the thought of being able to arouse a stripper felt like the epitome of sexual prowess…and all of a sudden I felt like I had something to prove.

In one fluid motion, Molly withdrew from my lap and slid to the floor, still facing me. She reached her arms up under my shirt, stopping around my shoulders and raked her fingernails all the way down my chest to my stomach. They stopped and rested right at the hem of my t-shirt. She then inched it up, ever so slowly, until it was sitting up past my belly button. I was so lost in how good the massaging and scratching felt that I didn’t realize that this now exposed the part of my dick that extended above my waistband. Snapping to attention, I look down to see Molly just eyeing it down. She looked so hungry for it, and it was then that I realized that I was actually powerless to deny her any desire she might have.

I reached down and grabbed the head of my cock between my thumb and three of my fingers. I let them rest there for a moment before I actually started massaging the head slowly. Again, it was my turn to be surprised by how turned on she seemed from watching me touch myself…and once I saw how into she was, I began to feel like it was *my turn* to try and put on a show for *her* now. I shimmied my shorts down, exposing nearly all of myself to her, and grabbed my swollen member fully with one hand. Her eyes widened then, as she realized just how big I actually am. I began to slide my hand along the full length of my shaft, which caused her to start licking those luscious lips of hers. I heard her give a dry swallow and take a sharp breath, as if she’d been so distracted that she’d forgotten to close her mouth or even breathe…and that was all it took for me decide that I was going to do whatever this woman asked of me.

I’d never masturbated in front of anyone before, and at that point in my life I hadn’t quite mastered the technique of doing it dry…so I imagine the “show” I was putting on for Molly was in fact a little more awkward than I was giving myself credit for. Regardless, she seemed to enjoy watching me jerk myself off for a couple of minutes. Whether she got impatient or just knew I wasn’t likely to cum just jerking myself slowly like that, I’ll never know…because the next thing I know, she batted my hand away and wrapped her lips around the tip of my cock. Somehow, there wasn’t an ounce of hesitation in my body; I just tossed my head back and enjoyed the feeling of her warm, wet hole massaging me. She teased me for what felt like an eternity…just dancing her tongue around the head, flitting it this way and that. It felt good, but if this was her sole definition of a blowjob, I thought was in for a little bit of a letdown. I figured someone like Molly would have a little more prowess.

Didn’t take long to get what I wished for…as I was contemplating whether this was the extent of her skills, she began to swallow my cock whole. I’d never been deep-throated before, and there wasn’t a thing I could have been told to be truly prepared for it. As I penetrated deeper in to her throat, it felt like it was literally trying to milk my cock of every last drop of cum I had. The sensation was unrivaled. She took about six inches of me before she couldn’t go any farther. As she released, she wrapped one of her hands around my shaft and began stroking me, using her saliva as lubrication. She caught her breath for a second, and then promptly wrapped those perfect little lips around me once more. This time, she kept her hand and mouth connected, blowing me and jerking me off at the same time. Any saliva left on my cock instantly became lube, letting her hand glide effortlessly in tandem with her mouth. Every once in a while she would reach that point where she couldn’t fit any more of my cock down her throat, and just hold her mouth there. Inside her mouth, I’d feel her swirl her tongue like crazy around my shaft, which was just the wildest sensation.

I knew I wasn’t going to last long. After about a minute of that, I told her that I was about to cum. No acknowledgement…she just kept going. To me, that was signal enough that whatever happened was not my responsibility. As I neared my climax, I bucked my hips up a little bit, flexing my cock as much I could. I didn’t say anything…there was just a short grunt as my dick exploded inside of her mouth and down her throat. Molly must not have been bothered by the streams and streams of jizz I was depositing into her mouth, because she *just kept fucking going*. The blowjob apparently wasn’t over. My hips would buck uncontrollably as her tongue passed over the tip of my cock, and I quickly realized that she was reveling in continuing to stimulate me in this hyper-sensitive state. I wanted to let her have her fun…I’d never been with a woman who was so cool about swallowing cum, and was doing a bit of reveling of my own…but the sensation was too intense, and I pulled away from her as she milked the last couple of drops out of me with her hand. I remember looking at her mouth and seeing that she didn’t need anything to spit into…she’d swallowed the whole thing.

There weren’t a lot of niceties afterwards. She got up and dressed pretty quickly. She went behind the mini bar and threw me a rag to clean up with, and I saw her rooting around the bar area looking for something else, too…but had a bit of clean up to do so I wasn’t really paying attention. As I was sitting there wiping myself off, she sauntered back over to me after a minute and grabbed one of my hands. Apparently, she’d scrounged up a marker from behind the bar, and proceeded to write her phone number down on my palm. I looked up at her quizzically, mildly surprised that was still where she wanted to go with all of this. She told me that she still wanted me to call her sometime, if I was up for it.

Back in the car on the way home, I was buzzing so hard. I must have been a little too quiet, lost in my own little world, because I suddenly became the focus of attention from my friends. They had seen me exit the room with Molly, and all wanted to know what happened. My mind had snapped back to my fiancé at this point. I didn’t know what I was going to do, but I certainly didn’t want one of these idiots to be the one who let the cat out of the bag. I decided to play it safe, as I knew they weren’t going to let me get away with telling them that all I got was a regular dance. I told them about she asked for my phone number, and they all started whooping and hollering, making a huge deal out of it. I told them I didn’t give it to her, though, and tried to put the whole thing to bed. It probably could have died there, but one of my friends just *had* to pipe up and say something to the effect of “She’s probably also a prostitute. She probably just wanted you on her client list.” Well…wasn’t *that* a curious possibility…

Over the next few days, his one little comment weaseled its way into my brain and wouldn’t leave. Things were awkward at home. I wear my emotions on my sleeve and I’m a shit liar, so my fiancé could tell pretty easily something was eating me up. I wasn’t focused on that, though…I was focused on needing to figure out whether or not my friend was correct.

I had to wait two days, when my fiancé had to work again, before I tried calling Molly. My heart was beating out of my chest, both because I was nervous about finding out what her deal was, but also because this basically felt like I was carrying out an affair at this point. Molly answered on the first ring, and seemed super thrilled to hear from me, which calmed me down a little bit. Figuring there was nothing to it but to do it, I stammered through asking her my question about whether or not she was a prostitute…and was surprised that she took no offense to it whatsoever. Then, she told me that she just genuinely found me attractive, and wanted to go out sometime. My curiosity quelled, I made up an excuse to get off the phone quickly, and just kind of left everything out in the open like that.

Two more days passed. It was still awkward at home, and I was still 50/50 on whether or not to come clean. Molly was still firmly entrenched in my brain…fucking her was like deciding to climb Everest…I just had to see if I had it in me. I called her again. No answer. I left a voicemail saying I’d like to take her up on that offer to go out sometime, and hoped she be free either that Friday or Saturday. A couple of agonizing hours later, I got a text…Molly’s number. Short and sweet, it just said I could pick her up Saturday night and had her address.

Saturday comes around and I nearly died waiting for my fiancé to leave for work. I practically followed her out the door I was so anxious to get over to Molly’s. On the drive over, I realized that the subject of my engagement had not come up since I initially told her about it; all of the thoughts that come with beginning to carry on an affair swirled through my head the rest of the drive over there. I was such a nervous wreck by the time I knocked on her door.

Molly managed to alleviate all of that from the second she answered, though. She cracked the door at first, noticed it was me, and beckoned me inside with a cliché “come hither” gesture. I slipped in the door, only to be struck with a view of her in a sheer black babydoll. I guess we weren’t going out. This getup was clearly designed with one purpose: to leave *nothing* to the imagination.
She grabbed me by my shirt and pulled me in close for a kiss. Her lips were so soft, I remember feeling like I might just melt into a puddle right there on the floor as her tongue gently entwined with mine. I won’t lie…the forbidden nature of what I was doing was certainly a bit of a turn-on that made the butterflies in my stomach kick into overdrive. After a bit of making out, there was no hiding the fact that I was starting to get an erection. I wasn’t wearing gym shorts this time, though, so my hard-on pressed against the interior of my jeans with a vengeance. As my member grew, I pressed in closer to Molly, letting her feel just how turned on I was already was.

I could feel the corners of her mouth turn up in a smile as she realized what I was trying to do. Slowly, she took one of the arms she had wrapped around me and felt her way down to the bulge in my pants. She teasingly petted my cock over the material of my jeans for a bit, before finally pulling down my zipper. Mind you, we haven’t even made it out of the foyer yet and I’m assuming she’s going to blow me again. Instead, I was in for a different kind of surprise.

She slid her hand in through the front hole of my boxers and ran it along the length of my cock. I was nearly fully hard at this point, but she managed to slide me out through the front hole of my boxers and jeans. She wrapped one hand around the middle of my shaft, turned away from me and just started walking…like my dick was some kind of leash. I was *not* slow to follow her lead…she led me back to her bedroom without ever looking back at me.

Once in her room, all clothing was quick to come off. She peeled my shirt off me, followed by getting down on her knees to help me out of my jeans. As I stood there with my rock hard cock right in front of her face, I tried nudging it in her direction, hoping she’d take the hint that I wanted those luscious lips wrapped around me again. She looked up at me with the coyest smile and said that she’d only do me if I did her. Feeling very comfortable that Molly was pretty much down for whatever, I responded in kind by suggesting that maybe we should sixty-nine.
We tumbled onto the bed and assumed the position. While my face had been inches from Molly’s pussy and asshole before, this time just felt different. I started by gently biting the insides of her thighs, working my way up to her pussy. As I let my tongue slide in between her lips for the first time, I felt the once-again amazing sensation of Molly taking as much of my cock into her mouth as she could fit. We carried on like that for what felt like ten minutes…the sensation of her lips wrapped around me drove me near to orgasm several times, but I could always double down on focusing on eating out her juicy little pussy, to distract myself from cumming too soon.

I was in heaven, and there wasn’t a bone in my body that felt like we needed to change things up yet…but Molly apparently had different plans. All of a sudden she sprang upward, inhaling deeply, and said that we’d clearly reached a stalemate (I had no idea it was a competition). She rolled over on to her back, tugged gently at my shoulder and indicated with her eyes that she wanted me to keep going down on her. I was happy to oblige.

Molly’s pussy was unique to me in that her lips and clit were quite pronounced. I’m not the kind of guy that finds that gross or anything, but I’d just never had the pleasure of being able to tease a woman’s pussy like hers before. I was having a blast, washing her with my tongue…and eventually, I inserted one of my fingers inside her snatch, exploring every inch inside of her. She began to moan softly, grinding her hips with my movement. After a couple of minutes, and another finger inside of her, she breathlessly begged me to tease her asshole too. I used one of my fingers that had been inside her, dripping with her juices, and gently began to explore around her asshole. The rhythm of her writhing changed slightly, and I soon realized she was trying to slide her asshole down on to my finger. Taking the hint, I inserted in gently, met with more moaning.

I figured it was time to shit or get off the pot, so I really began working every angle trying to make her cum. After a couple of minutes of furiously fingering her pussy and ass while focusing on her clit with my tongue, she began to moan *really* loud, letting me know that she was cumming. Her hips bucked hard against my face, and then her body just collapsed in on itself, all tension in her muscles seemingly dissipating all at once. I flicked her clit with my tongue playfully a couple more times, just to watch her spasm with pleasure. She slapped the top of my head playfully, and told me to stop fucking around and come kiss her.

I’m a man of habit and routine…and one of my habits and routines was whenever I finished going down on a woman, I’d find some way to clean my face off afterwards. Molly wasn’t about that at all. She noticed I was searching around for something, and about to just head to the bathroom when she grabbed my arm and pulled me down on top of her…giving me a deep, passionate kiss. She had to have been tasting herself, which really turned me on.

As we kissed, she reached a hand down around to my cock, and gently guided it inside of her still sopping wet pussy. I’d never entered a woman so easily before, and we instantly developed a perfect rhythm with me on top. One of my favorite things to do when I’m on top is change up how our legs are intertwined. Starting with both of my legs inside of hers, I’d kick one of mine up and over hers, and then eventually straddle her completely, and then switch to having the other leg kicked over one of hers. Molly seemed to love this, as it seemed like she was off in her own world as I fucked her. Her head was thrown back, her eyes were closed, and she was being extremely vocal…which was a major turn on. It wasn’t dirty talk, but just a lot of moaning, Yes’s, Oh’s…that kind thing.

I was in a zone of my own, but really didn’t know if Molly could cum from intercourse, so I just kept trying to avoid cumming as much as I could by changing my pace. Eventually Molly snapped out of it, and said we should change positions. She pushed me off her, and rolled over on to all fours, beckoning me to fuck her doggy style. I was quick to comply. Molly’s ass was perfectly round, and had the most incredible bounce & jiggle as I railed as much of my cock into her as I possible could. As I’d get close to having nearly all of myself inside of her, she’d back her ass up a little more, like she was craving every single centimeter of me. She was one of only two girls I’d been with who could take me to the hilt without complaining, and it was really getting me going. As I fucked her, I reached one hand around and tried playing with her clit. It was a little hard to keep rhythm and balance while doing this, but every once in a while I’d touch it just right and would feel her whole body jolt with electricity.

After a while, Molly pulled herself off of me and reached toward her nightstand drawer, pulling out a bottle of lube. She turned around, poured a heaping amount of lube in to her palm and began to massage my cock with it. Now, she was still wet as fuck…there hadn’t been any issues so far, so I was a little confused. Once she had me all oiled up, she reassumed the doggy style position, looked over her shoulder, met my eyes directly and told me to fuck her in the ass. I’d tried anal once before, and it *did not* end well, so I stupidly asked her if I needed to go slow. She said yes, but only in the beginning and that it wouldn’t take long for her to stretch out a little bit.

I did as she requested, slowly pushing the tip of my cock into her asshole. It took some doing, but after a bit I had a couple inches inside of her and was loving the feeling. Molly’s pussy hadn’t really been that tight, so this was a massive change of pace. The first couple inches were pretty easy, but after that I could tell it was going to be hard to fit much more of myself inside of her. Once I figured out where the absolute stopping point was, I really got into a good rhythm. She seemed much more passive while I fucked her in the ass…I don’t know if it was just harder to concentrate, or if I was hurting her but she didn’t wanna say anything; I don’t really know. Either way, with the lube I was able to get going pretty good, and knew I was going to cum soon.
I exploded inside of her shortly after, trying not to go too deep but wallowing in the pleasure at the same time. My orgasm took her my surprise, as I heard a surprised little yelp, followed by some gentle moaning and purring as I stayed inside of her until every last drop had left my body. As I pulled out, a thick stream of my semen followed, dripping down over her pussy and on to the sheets below. We both collapsed in a sweaty heap, not giving one flying fuck about cleaning up.

We actually passed out like that…which is exactly how I got caught. I woke hours later to hearing my phone going off in my pants pocket. My heart sunk, as I knew exactly what was going on without even looking at a clock; my fiancé was home from work, and I wasn’t there. No need to really embellish this portion of the story…I’d been caught red-handed, and she broke off the engagement. That’s pretty much the end of it (well, what’s worth sharing here at least). Unfortunately, probably due to the panicked nature in which I bolted out of her apartment to run home to my fiance…I never saw or talked to Molly again.

Source: reddit.com/r/gonewildstories/comments/62qgws/mfcheating_destroying_my_engagement_with_molly