This happened about 7 years ago, and while not the first time crossing the lines physically outside of my marriage, it was the first time I had sex with a woman other than my wife. To make sure this point is clear, I lost my virginity to my wife while we were dating and then went on to marry her. So up until this story, she was the only woman I’d ever had sex with.
I had been toying with the idea of finding a friend with benefits for a while, and had met up with a few women here and there, but none of them seemed to be what I was really looking for, and aside from some make out sessions, fingering, and blow jobs I was still looking for someone. I ended up posting an ad on Craigslist and I was brutally honest with where I was. I indicated I was married, and tired of being alone.
I got a reply from Kim, a woman who lived in a nearby town. She told me she was married, but that she and her husband had grown apart. She wasn’t really sure if she wanted to get a divorce, but knew something needed to change, and so she had already moved into their guest room and wasn’t even sharing a bed anymore with her husband. She was also starting to look for a place of her own as she wanted to do a trial separation from her husband and see how that went and reevaluate where they were.
We got to texting non-stop getting to know each other. She was a teacher, had curly dark hair, short, glasses, a bit nerdy but in a cute/quirky kind of way. Our chatting turned sexual as well, and we’d spend many evenings sexting back and forth telling each other how we’d like to get off, what we’d do to each other, what we wanted to try, and had many orgasms over chat. She loved me sending her pictures of myself playing when we were chatting and I’d often ask her what she wanted to see, and her general response was always that she wanted to see my cock in her mouth, or pussy, etc.
We contemplated options for meeting up, could we meet up some where between our towns and find a side road and have sex in the car, or could we figure out a way to make something work. Well, our opportunity finally came when she found a place of her own to rent for her trial separation. She’d spent a week getting it ready, getting some furniture, cleaning, etc, but hadn’t yet moved in. I think she was nervous to take that leap, but our sexting convinced her it was time, and so we ended up arranging our first hookup to take place at her new place, the first night she stayed the night.
Well, that night came and I had told my wife I had a project at work that I needed to complete after hours as it would end up causing network disruptions that couldn’t happen during the day. Instead, I picked up a bottle of Kim’s favorite wine as a house warming gift and headed to her place. We had discussed that she had a bit of a strangers fantasy, and even though we’d been chatting, we’d never met, and so our plan was that when I showed up, we wanted to kiss without exchanging any words and go from there. It’s important to note that while I was extremely excited, I was also extremely nervous.
So I arrived that evening, my heart racing and handed her the bottle of wine. She took it to the kitchen and returned, walked directly up to me and we started making out. We stood there in her living room making out for a bit before we decided it would be more comfortable if we moved to the couch. Kim was only 5’2″, and with me being 6’3″ there was a bit of a height difference for our standing and kissing.
We moved to the couch and I sat down. Kim stood in front of me and took her shirt off, before straddling me on the couch and resuming our making out. My hands began to wander and I was exploring all of the places on her body that I’d told her I wanted my hands to be. They were on her back, her sides, her thighs and legs, her breasts. Soon my hands were behind her, unclasping her bra as she took it off and tossed it to the floor. Feeling her breasts for the first time was amazing, and soon our kiss had broken off as I moved my kisses down her neck and was soon sucking on her nipples. She worked my shirt off while all of this was happening, and feeling her flesh against mine was such a hot feeling. We kissed some more and soon my hand was rubbing her pussy through her yoga pants.
She stood up, slipping off her yoga pants and panties and dropped to her knees in front of the couch and started unbuckling my belt. My belt undone, button and zipper to follow and soon she was pulling my pants and underwear off and tossing them to the side. I watched as she took my cock into her hand stroking me and then lowering her mouth to take me in. I loved watching her take my cock and it felt so good the way she was working my head with her tongue. She worked my cock over for a bit, getting me good and hard, but she wanted more. We fished a condom out of my jeans pocket.
My heart still racing from nerves, I get the condom on but I can already feel that my erecting is fading fast. Kim climbs into my lap lining my cock up with her pussy and begins to lower herself onto me. It works, but not great. She stops and stars to stroke my cock again, helping me to build back up my erection, and it works, but as soon as she stops it’s fading…damn nerves. We’d discussed previously that outside of our spouses we’ve not had sex with anyone else and we were both clean, but she wasn’t on birth control, which was the main reason we were using the condoms.
I suggested that perhaps the condom was desensitizing me too much, and we both agreed to ditch the condom and try it raw. She suggested maybe we also move from the couch to her bed, so I follow her naked body into her room Damn she looked good.
We got to her room and I laid down on the bed and Kim again took my cock into her mouth and began giving me head. I could feel my cock growing in her mouth, and soon I was hard and ready to try again. She moved over me, taking my cock into her hand and I felt her pussy wrapping around my shaft as she lowered herself onto me. It’s hard to describe what it was like, but it felt amazing to be feeling another woman surrounding my manhood. Kim was riding my cock, and I slipped one hand between us and began to rub her clit, while my other hand was fondling a breast. She rode me like that and it didn’t take me long before I was on the brink of cumming. I told her I was close and she climbed off of me and once again took me into her mouth as I exploded.
Kim climbed back up beside me and laid down on the bed and said “Hi”. We started talking a bit, and I told her how incredibly nervous I was and that my heart was racing the entire time. We laid there naked in her bed talking for what seemed like an hour. Talking about things we’d chatted about, talking about the sex we’d just had, talking about the music that was playing, and the more we talked, the more I relaxed and calmed down.
We were laying there talking, music playing, and Kim moves closer to me and we start kissing again. My hands are exploring her naked body, and soon we’re grinding our bodies together with desire and my cock is standing at full attention and ready to play again. I moved off of the bed and pulled Kim to the edge of it. This time I dropped to my knees and soon my head was between her thighs as I started to eat her pussy. I gave it some long slow licks, letting my mouth fill up with the taste of her pussy, before I turned my attention to sucking on her clit and massaging it with my tongue. Meanwhile my hand slipped up beneath my chin and I slipped two fingers inside of her and began slowly thrusting them in and out of her. Pretty soon her hands were holding my head and she was moaning, followed shortly by her cumming hard.
I moved back onto the bed, kissing my way across her stomach, breasts, neck, ear, and soon her mouth and she gasped as I glided my cock back into her pussy again. Seeing her laying naked beneath my body as I was sliding my cock in and out of her was a sight that’s seared into my memory. I fucked her missionary style slow at first, but picking up speed as I went. My thrusts were long and deep and she was moaning as I worked her over. I remember at one point thrusting into her especially deep and she let our a sharp little yelp. I asked her if she was alright and she acknowledged she was fine, but commented about how deep inside of her my cock was. We fucked like that for a while before she turned over and head me fuck her from behind. I was fucking her and watching her ass while wrapping an arm around her to finger her clit again and soon she was cumming again.
I’d had about all I could take and as I was still fucking her doggy style could feel my orgasm building. I pulled out at the last moment as my first contraction was starting and unloaded on her ass.
We cleaned up and soon were back to chatting in her bed. We ended up fucking one more time that night. She wanted to be on top again, and so she rode me making herself cum and kept riding me until I was on the verge of cumming. She waited just a little to long to stop though and I started cumming while I was still inside of her, but for the third orgasm in the span of a few hours there wasn’t too much there.
I suggested that I was still going to swing by the office before going home because we had a shower there, and I wanted to clean up before going home. Nothing like smelling like sex when I return from a night at the office. Kim suggested I could just use her shower, so soon we were both making out under the hot water. I cleaned up, and before we got out of the shower, she was back on her knees with my dick in her mouth. I didn’t cum, but watching her wet naked body, looking up at me with her green eyes, my cock in her mouth was truly a hot moment.
We dried off and got dressed. We made out a little bit more just before I left. I still went over to the office before going home. The job I told my wife I would be doing was actually a pretty dirty job, so despite having just showered off, I went and got myself covered in dust before heading home. The things we do to try and cover our tracks
Question for those reading: What are some of the funny/quirky things you’ve done to cover up what you were really doing?
Source: reddit.com/r/gonewildstories/comments/ineo2y/craigslist_success_the_married_teacher_mf