My [F]irst time with another woman was with a MIL[F].

I’ve always known I was bi, but had never experimented with a woman outside of playfully kissing other girls at college parties. After college, and the end of a long, dreadful relationship, I was ready to explore my sexuality and do things for me for a change.

I continued to date men, but kept the thought of women in the back of my mind. I watched a lot of lesbian porn, but mainly because it was what got me off the fastest. Never really had much intention of going after women despite being sexually attracted to them. I always have, still do, and likely always will prefer men. I’d say I’m 90/10 bisexual.

Anyway, after a couple of years of lame first dates, underwhelming hookups, and short lived relationships with every douchebag you can think of causing some sexual frustration, I amped up my curiosity about women. I started to fantasize about it on a more regular basis, and ended up being led into lesbian MILF porn, which drove me absolutely wild. It was fun picturing myself as one of the girls in normal lesbian videos, but really associating myself with the younger girl in young/mature videos would get me wet just thinking about it. It consumed me for a couple of months.

Before Craiglist personals were gotten rid of, I started to make some ads. I’d put up a couple of pictures of myself, usually just in my underwear. Of course, I got responses from men. Lots of men. But a good amount of women came through as well. After maybe a month of posting, getting frustrated, and deleting just to get horny and post all over again, I finally got an email with pictures from a woman almost twice my age.

Her pictures weren’t graphic aside from one in which she was in a bikini. Her name was Erin, and hey body was delicious. Curvy, long blonde hair, and according to her first email, she was about 5’11”.

I’m 5’4”, have medium length brown hair, and am pretty petite. I have curves and I’m very proud of my ass, but I don’t have a lot of power in the Titty Committee. We were pretty opposite in every physical aspect. Imagine Anna Kendrick next to Sofia Vergara.

So we emailed back and forth for a couple of hours, just discussing our situations. I told her all about my curiosities and why I placed the ad. She explained that she was recently divorced and was diving off the deep end of experimenting with women. She’d had a handful of partners over the last year or so, and had gotten quite a bit of experience.

We ended up exchanging phone numbers and texted for about a week. About normal stuff, and explicit things. We shared a few lewd photos and she had me explain to her in detail what I wanted.

I loved the nurturing aspects of the porn videos I’d been into lately, and told her I wanted to be completely guided and essentially told what to do in a feminine way. She loved the idea.

So the day came when she finally asked me over. It was a Thursday evening. I was on my lunch break when she finally made the move.

“I want you to come over tonight. We’ll start your lessons.”

I almost came while downing a salad in my car. I replied, “Yes ma’am.”

The last 4 hours of work were hell. I was sopping wet almost the entire time, and the anxiety was making me shake at times. Finally 5pm rolled around, and I asked her for her address. I put it in my phone, and spent the entire 25 minute drive to her house trying to talk myself out of it.

I pull up, and park in the street. I was so nervous I was shaking uncontrollably. I kept telling myself this was a sign to leave, but I knew I’d end up regretting it the next time I got horny.

So I shut my brain off, got out of my car, strolled up to her door and knocked. She promptly answered and welcomed me in. We awkwardly made small talk about my drive, our days, etc. She gave me a quick tour of her house, and we ended up back in the living room.

We sat on the couch together and continued to chat. I realized I wasn’t horny anymore, just nervous. I started to think up excuses to leave. I even set an alarm on my phone while sitting there to go off in 15 minutes so I could fake a phone call.

Before the alarm could go off though, she broke the tension. “You know, 26 and 48 is enough of an age difference that I could be your mommy.”

Tingles. She moved a bit closer and touched my leg. I just giggled and allowed her to stroke my thigh a bit and lean ever closer.

I don’t even remember the words we were saying, because evenually she put her fingers under my chin and kissed me. One quick kiss, before a firmer kiss that lasted a bit longer. Suddenly her hand was on the back of my neck and her tongue was in my mouth. It felt so strange, I’d only just met this woman. But I responded with my tongue. We made out, nibbled lips, and kissed for what felt like ages. She finally pulled back, leaned back into the couch, and told me to get more comfortable.

She had me stand up, and strip down to my bra and panties. Once I sat back down, she stood up and did the same. Except she was in an all black garter set. I was taken by surprise and she noticed.

She sat back down and pulled me over to her. She had my almost in her lap, kissing me and running her hands all over. She kept putting my hands on her hips, or over her bra, but I was too nervous to really explore.

Finally, she made some space between us and took off her bra. I’d seen pictures but holy shit. These things were gorgeous. I immediately felt self-conscious of my own little ones.

She grabbed my hand, and put it over her left one.

“Just squeeze and play. Run your hands all over them.”

I clumsily went for it. I started to rub and stroke them. I took a little risk and started to finger her nipples and pull on them a bit. She moaned with pleasure. “That’d be even better if you were using your mouth.”

I started to lean in, but she stopped me. She turned me around, unhooked my bra, and then laid me on my back across her lap. Before I knew it, she put her hand under my head, and pulled me up, so my mouth was right at her nipple.

“Just suck and lick it nice and slow.”

I opened my mouth, and for the first time I was really having a real lesbian experience. I sucked it, and flicked it with my tongue while playing with the other one in my hand.

“That’s such a good girl.”

She pushed my head into her tits and had me alternate back and forth for what felt like 10 minutes. She was running her hands all over my body the entire time, pulling on my nipples and teasing me over my panties. Once she’d had enough of that, we stood up, and she led me by the hand to her bedroom. She laid me down on the bed, flat on my stomach. She propped herself on all fours above me, and started to kiss the back of my neck. She ran her hands down my back and sides, and kissed down my spine. She got to my ass and sat back on her knees. She rubbed it, and spread my cheeks to get a good look at everything. This made me super self-conscious until she said, “This is the best view I’ve ever had.”

She massaged my ass for a bit, and traced her fingers along my pussy and asshole. Now, I’d never had anything done to my ass ever. I got a little nervous. But she focused mainly on my pussy and started to push her fingers in and out. She kept my ass spread with one hand, while she worked her magical fingers. I was dripping wet, I could feel it, and before I knew it was was cumming in her hand.

She called me a good girl again, and pulled me up on all fours. She got on all fours behind me, and used her mouth this time. It took almost no time at all before I finished again. She knew what she was doing. She buried her face and my tongue in me until I came a third time. I was convulsing from the pleasure when I felt her run her mouth up a bit. Before I knew it she was tonguing my asshole. I was in such ecstacy I didn’t even mind the weirdness of it. She put her fingers back inside my pussy and ate my ass with as much passion as she’d eaten the rest of me. I told her I was about to cum again, and she got me right to the point before pulling her fingers out. She put a hand on each side of my ass and it felt like her tongue was 6 inches deep in my ass. I thought it would ruin my orgasm, but sure enough, the insane pleasure I was feeling for the first time in my life pushed me over the edge. It was so intense I couldn’t stay on all fours anymore. I collapsed onto my stomach on her bed, gasping for breath. She smacked my ass and said “Babygirl I could eat that all fucking day.”

I wanted to take her up on it, but I needed a break. I rolled onto my back and tried to calm down. I had my eyes closed, and relaxed while she ran her fingers all over my body. Once I’d calmed down a fair bit, she stood up next to the bed and removed her panties, leaving the garter belt, straps, and thigh highs. She pulled me up from the bed, and pulled me into a kiss. He lips still wet with my cum. She put her tongue into my mouth again and made sure I tasted myself still in her mouth.

She took a small step back. “Why don’t you get down on your knees for me, honey?”

I did as I was told and she stepped forward again. I kissed her abdomen, and she lightly held my hair on the back of my head. I kissed below her belly button, and put my hands on each of her hips.

Since I was so short, and she was a pretty tall woman, it was easy for me to just lower myself a bit and have easy access. I did so, she opened her legs a bit, stepped forward with her right leg and gently pulled my eager mouth against her pussy.

She was shaved bare, and I’ll never forget that first moment of feeling her pussy in my mouth. Wet, and warm. And so, so soft. I kissed at her lips, and ran my tongue up and down. She moaned and stroked my hair. “Just do what you’d want me to do to you.”

I kept going, and she gradually got slightly more aggressive with the hair holding and head pushing. “Open your mouth and hold your tongue out.”

I did it, and she used my hair to pull my head up and down, using my mouth to get off. She stopped doing that after she noticed I needed to breathe a bit, and said “make mommy cum.’

She pulled her right leg up and placed her knee on the edge of the bed. She went back to holding my hair lightly and played with her left nipple with her left hand. Her hips really started to grind her pussy into my mouth. “Yes baby, yes. Don’t stop. Right there, suck on my clit.”

Before I could register that she was cumming, she started moaning so loud with that shaky orgasm voice. I reached my hands around to her ass, and pulled her closer to my mouth and kept sucking and licking. It seemed to last for so long. I could feel her pussy pulsing in my mouth, and finally it got to be too much. She grabbed my hair and pulled me away. She stood over me, still holding my hair, looking down with a smile. Breathlessly she said “There’s a taste of mommy for you.” while she used her thumb to wipe her cum from my lips and chin.

“One more time babygirl. From behind.”

She turned and walked to the wall. She leaned her arms against it, spread her legs and pushed her ass out. I crawled over to her. “Just worship my ass, and I’ll do all the hard work.”

Again, I put my hands on her hips, and started to kiss all over her ass. I squeezed it, and gave each cheek deep kisses and quick little licks. She kept her self propped on the wall with her left hand, and used her right hand to rub her clit. I spread her ass and was trying to get my mouth to reach her pussy, tonguing it a bit. “No baby, eat mommy’s ass.”

I felt weird about it, and kind of went back to kissing and licking the under side of her ass cheeks. “Eat my ass, honey. It’s okay. If you don’t like it you can stop.”

I spread her ass again and took a look. It didn’t seem like something I’d enjoy doing, and I really wanted to eat her pussy again, but I remembered not thinking I’d like having my own ass eaten either. So I went for it. Broad licks against her ass, tightening my tongue to push it in a bit, I tried it all but it was way harder than eating her pussy. “That’s such a good girl!”

She kept calling my good girl again and again, and every time she said it it was so hot. I’d told her all about my recent porn habits of older women/young girl videos, and I guess she’d done some viewing of her own because I could tell she was trying to use that turn on to her advantage.

Eventually, she came again, with me taking long licks from the edge of her pussy to the top of her ass. She turned back around and stroked my hair again.

I stood up and we both collapsed into the bed. We laughed off the high, and she asked me to run my hands and fingers all over her.

She propped herself up against her headboard eventually and had me suck on her tits again for a good long time. It was so relaxing and fun. Then we each went down on each other one more time, just lying on our backs. I noticed that it was dark out, and told her I needed to leave. She offered to let me stay, but I had work in the morning and no fresh clothes at her house.

So I dressed in the living room, while she watched me from the hallway. She stayed in nothing but her garter outfit.

I suddenly felt awkward again, but she walked over and kissed my goodbye. I left, drove home in complete silence, made myself a quick dinner, and went to sleep. Nothing else was in my mind aside from what had transpired that evening.

I thought about it almost constantly for the next couple of days. We stayed in contact, kept sending nudes to one another, and she asked me every day for a week to come back over.

I declined each time. For whatever reason, now that I’d gotten it out of my system, I had no interest in it anymore. It was fun. It was ecstasy. It was taboo that she was 12 years older than me, it was hot that we played mommy/girl the whole time, but that’s where it stopped.

I feel more satisfied than I’ve been in years. And that’s good enough for me. I’m ready for a relationship, and a normal and regular sex life again. But who knows. Maybe I’ll go bury my face in that amazing ass again one last time, or nurse those amazing nipples again before I move on to the next phase of my life.

Source: reddit.com/r/gonewildstories/comments/a1jvnl/my_first_time_with_another_woman_was_with_a_milf

5 comments on “My [F]irst time with another woman was with a MIL[F].

  1. As a straight, married man (52 years old & Married for almost 30), your story got me incredibly turned on! You have a magnificent writing style, and the way you expressed your own feeling each step of your adventure was sensational. I was only disappointed that you haven’t returned for more from “Mommy.” But, you did leave a bit of a cliff hanger, so…

  2. The way you described your nerves and getting the shakes was so real. I was immersed in your story.

    You should go back, pack a duffel, and stay the night just to enjoy the after cuddles through the night and pancakes in the morning.

  3. Awesome story! Even thought I’m a man – my fav porn is older/younger lesbian stories – and your experience is awesome! Thanks for sharing and I hope you can have another FF romantic adventures… It would be great to watch some basic photos of your body, to have a better scenario of your story lol… Just saying!

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