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My [M] Cheating Stories - Emily
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lostinTheNL2021 is a male
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You can read my first post here, in which I talk about Amanda. 

The second FWB I want to talk about is Emily. Like Amanda, we met over Craigslist Personals. After a few weeks of chatting, we learned some things. First, we were both teachers and second, her mentor teacher was literally the teacher across the hall from me. I had started working at that school the year after Emily’s student teaching. It was winter, and an especially snowy one. Our school district had announced they were closed for the week. Opportunity.

Emily suggested it first. I should come over. I wasn’t sure that I should, though I wanted to. She managed to convince me with something so simple. She said that if I did come over, would I be okay not using a condom? She had an IUD, and she wanted it raw. I didn’t need to be asked twice. It was around 11pm and I drove carefully over streets where ice was made invisible by the lack of light. Made it there alive. I knocked on her door, and Emily was there, in person, for the first time.

I have always gone for bigger women - thick, curvy, fat, plump, BBW; I don’t know which word to use; I just love women with thick hips and/or full breasts. Love you skinny ladies, but just not for me. She had shoulder-length brown hair and a very mischievous smile, like a kid up to no good. Like me, she wasn’t single either. She’d been dating a guy for about two months, unsure how serious it was, but he didn’t know I was coming over before or after it happened. And he didn’t get to have her without a condom.

We sat on her sofa. We chatted for a bit. She made tea. It was nice. I don’t like to jump right into it immediately, nor did she. The distance between us closed over the next half hour on that couch, until her leg was over mine, I was kissing and nipping at her neck as she laid back. She quickly unclasped her bra, starting a clothing pile in her living room. My hand found a breast, full and overflowing in my hand. Her nipple grew harder from a pinch and teasing bite.

It didn’t take long before we attempted to move from the couch to her bed without breaking from our kiss, our greedily grabbing at each other. When we hit the mattress, everything was on the floor, and skin touched skin. My fingers kept track of how ready she was, helping her along by rubbing her clit and sliding two fingers inside, stroking them in and out. Emily grabbed some lube on her bedside table and got me slick, stroking me until my head was so good and swollen. 

Emily looked up at me as I moved down between her legs. During our chats, I had mentioned that I love eating a woman out, and several women, including my girlfriend, had complimented me on it. Emily wanted that, and I was going to deliver. Starting softly with kisses and soft bites on her inner thighs, my nose brushing across her clit, warm breath. Then a nice long, slow lick from bottom to top, flicking across an already swollen clit. Licking it, sucking it. My fingers joined in and pushed in deep. Few women have soaked my fingers like Emily did. Her hips bucked, and I wrapped an arm around her thigh, making sure she wouldn’t squirm away. I wanted her to enjoy the intense feelings. She did, screaming out, shaking; I didn’t stop until she was panting, telling me, “Time out.” I emerged from between her thighs, smiling. She tasted herself on me as we kissed.

I reached down and teased her with the head, rubbing it up and down those juicy, wet lips. She put a hand on the back of my neck and pulled me down for another kiss. Tongues playing together between the smack of lips. I pushed in. She took me, opened up, and then clenched tighter than my girlfriend ever had. I always find it hard to describe realistic sex without sounding like a cheesy romance novel. It just felt good. Both of us wanted it so much. My cock was raw inside her, long deep strokes, kissing her cervix with my cock. Hands were greedy, that feeling of loving all of this but unable to satisfy the current hunger yet. 

This would be repeated several times that night. I slept over. The first time was just a warm-up. The best happened about an hour later. Emily had her legs in the air, slightly bent over my shoulders. I was in to the base of my cock. I felt that build of pressure begging for a release. I looked at her and said, “I’m so happy I was able to come fuck you how your boyfriend couldn’t.” She clenched, my cock got slicker, strokes got harder. I reached over and accidentally grabbed a curtain too hard. It came falling to the ground. Emily just laughed and said, “I love that.” She took her second of four loads a minute later. I didn't pull out until she'd milked every drop from me.

We would hook up several more times until my girlfriend moved across the country in September of that year. I spent a whole weekend at Emily’s place when her boyfriend was out of town. She learned about my breeding kink and wanted to play that all weekend. She’d say, “I want to make you a daddy,” as I pumped inside her, knowing that just the tone of voice, the look to give me, the tightening of her pussy to make me cum hard.

Those were such fun times. The last time I checked in with her, she was still teaching. She had a serious partner and was happy. We exchanged a few brief, kind messages, but our lives had moved on. The third FWB was a university student living near my apartment. That’s for another time, though.

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