[M/F] An Affair with my MILF tutor

When I was in high school, I had an affair with my tutor. I was 18 at the time, and she was in her 40's and separated from her husband. Kirsten had been my tutor for two years at the time, and we had grown very comfortable with each other. We were productive during our tutoring sessions, and usually finished up before the 1.5 hours allotted. As a consequences, we chatted and gossiped a lot about girls at school, her other students, and life in general. We could bullshit with each other for hours, and I really began treating her as a friend. I would text and call her when I was bored or needed advice on non-academic matters in my life. She heard about the girls I dated, and occasionally I would pry into her personal life as well. She wasn't officially divorced from her husband, but he lived in another country and she wasn't dating anyone.

One night, I called her at around 11PM just wanting to chat. She was coming home from a dinner with friends, and it was clear to me that she had been drinking. At one break in the conversation, she sighed, "When I was younger, I was crazy about this guy that was just like you." With a laugh, I replied, "If you were younger, I'd be chasing you, hard." She gave a quick sexy moan, giggled, and told me I was sweet. We said our good nights and hung up. Afterwards, I was rock hard and had to jerk myself off before sleeping.

Things between us changed subtilely afterwards. I began flirting more during our tutoring sessions, and I would blatantly let myself get caught when checking her out. There was a lot to look at, frankly; she was 5'0, skinny with B cups and always wearing tight tops and knee length skirts. She would blush every time I looked at her but we would always maintain eye contact. She complimented me a lot. I'm a lean, 5'8" Asian guy and have been told that I'm attractive.

One day, we're sitting on the couch, right next to each other. I can't remember what we were talking about, but during a break in our conversation I turn my head and look down at her, into her eyes. We smile while looking intensely at each other, and I go for it. I kiss her, softly and gently. I move my arm around her and wordlessly pull her closer to me as she lets out a soft moan. It's a romantic kiss with that indescribable feeling of exploring each other's lips for the first time.

I slip my tongue into her mouth to meet hers, and at that movement, the romantic kiss became nothing but lust and hunger. I shifted her over onto my lap so that she was straddling me, and I placed my hands on her ass, underneath her skirt. I used my hands to grind her pussy against my achingly hard cock, and she let out a deep, desperate moan. "God, I've wanted this for months but it's so wrong," she moaned as she get devouring my lips and neck and grabbing at my hair. I slip my hands underneath her shirt and bra and pinch her nipple, eliciting more sexy moans from her.

She suddenly came to her senses and tells me, "This is wrong; we need to stop." I took my hands out from underneath her shirt and hugged her tight. She stayed on my lap, lightly grinding on my cock, as we talked about how much we meant to each other between kisses. After 30 minutes, I have to leave to pick up my sister as she wouldn't stop calling my cell phone. We kissed passionately, and I left, unsure of where things were.

Needless to say, I came 4 times by myself that night. I was a virgin at the time, and this was the sexiest experience and fantasy of my life so far. I had had a few blowjobs and handjobs in the past, but nothing even came close to this.

I went back to see her the next day, immediately after school. As soon as he closed the door, I pushed her against the wall and ground my hips against her, making sure that she felt my hard on. I picked her up and she wrapped her legs around me as she scratched my back. She kept on telling me that this was wrong, that she older than me, still technically married, and my tutor. But I didn't care. I wanted her.

I put her down, and she took my hand and led me to her bedroom. I slipped my hands underneath her skirt and pulled down her black panties, which were noticeably wet. We slowly stripped each other's clothes off one at a time. My inexperience began to show as I struggled to take her B cup bra off. She laughed and took it off for me. I stared at her tight, perky boobs before bending over and devouring her nipples with my mouth and tongue. I expected them to be slightly saggy with age, but they were beautiful and soft.

She fell onto the bed, with me on top of her, still sucking her tits. I moved my right hand between her legs and began fingering her. She was so tight that I had to start off with one finger, but pretty soon she was moaning and screaming out my name. Her whole body tensed, writhed, and bucked as I stimulated both her nipples and her pussy. She kept on saying over and over again, "God, this is so wrong. You're so sexy. I haven't ever felt like this." It was wrong, but because it felt so wrong, it was hot.

I was inexperienced and didn't know how to make her come, so after 10 minutes I stopped stimulating her to give her a break. I lay on top of her, between her legs, but average but thick, 6" cock resting against the outside of her soaking wet pussy. I blush, and I whisper in her ear, "I've never done this before."

"You've never slept with an older woman?"

"No, I mean…I've never had sex before."

"Are you sure you want your first time to be with an old woman?" she said, but I reassured her that I wanted her to be my first and that she was absolutely gorgeous. Kissing her, I lined my cock up with the opening of her wet pussy and pushed in slowly. No condom, just my bare hard cock inside of her extremely tight pussy. I had no idea that sex felt this way…so moist, wet, hot, soft, and tight.

She let out a deep, gutteral moan and told me to slow down because I was bigger than she was used to. She hadn't had sex in 5 years. "Just don't come inside me. I don't have birth control," she whispered. I awkwardly pumped in and out of her slowly because I was trying so hard not to lose it in 30 seconds. After a minute, she could tell I was tensing up and she moaned, "come for me. Just come for me, please." Those words were so sexy that my cock began pulsing immediately. I buried myself deep inside her and had the most explosive orgasm in my life as she reached up, grabbed my head and pulled me in for a passionate kiss.

I stayed inside her for the next minute, both of us enjoying my cock and cum still inside her. "Shit," I muttered, "I couldn't control myself." She told me it was okay and hugged me as we kept making out and exploring each others bodies with our hands. She told me it was so cute how I came so quickly, but that I would get used to the feeling. She felt so sexy that she was still attractive and able to get a young guy like me to come so quickly.

She got up and told me to stay put as she went down the street to the pharmacy to get plan B. When she got back, I was still naked on her bed and again, rock hard. Without even first taking off her clothes, she quickly knelt down, and took me in her mouth. In all honesty, it was a bad blowjob with lots of teeth. She told me afterwards that she had never given her husband a blowjob, but that with me, all she wanted to do was to anything to please me.

We fucked the rest of the afternoon. During our fifth session (yay for being a teenager), she got on top of me and rode me to an orgasm. Her face turned bright red as her body tensed and she threw her head back. She came, loudly. As soon as I felt her pussy clench around my cock, I released inside her. It was one of those rare moments of simultaneous orgasm that I won't ever forget.

We kept seeing each other until we went to college. After I came back, I reconnected with her, which is another story. I hope you enjoyed this story!

Source: reddit.com/r/gonewildstories/comments/42is46/mf_an_affair_with_my_milf_tutor