[M]y first experience o[F] sex with a lesbian

I'm a guy. This is my first time posting here, so I hope I got the tags right!

My first time was off of Craigslist. (That dates this story already.). I had posted a jokey ad, calling myself a good "Mr. Last Call", saying I would be happy to come and meet a woman on her way home from a bar, and we could go back to my house for whatever: sex, cuddles, pancakes, drunken discussion of semiotics, etc. I wish I could find the text of these ads I used to post, but when CL purged Casual Encounters, they also purged all of the ads that had ever been published, so they're not in my CL account anymore. I really enjoyed Casual Encounters, because it was text-posts, which I love (obviously), because to me, few things pass the seductive promise of the written word.

A woman sends me an e-mail through this ad: "wow, you seem like a really polite and respectful guy. I'm a lesbian, and I've never had sex with a man, and I want to, and I choose you, based on your ad. Do you want to meet for drinks to confirm?"

Heck yes, I do. (I'm already in, of course, because it's a woman who wants to sleep with me, but I'm going to meet for drinks so we can feel each other out and make completely sure.)

We agree on a bar, and all that day at work, I am giggly, like, I can't believe my luck. I'm excited.

Evening comes, we meet at the bar at the pre-arranged time. We both have a couple of drinks at the first bar, and we're talking, getting to know each other. She says "I'm curious how you could even find me attractive, because I'm a lesbian. I will be flattered if you're even able to get it up for me."

We decide to head on to a second bar, and get some food. At our second bar, we're both tipsy, and she is getting bold, starting to touch me under the table. She then announces she needs to use the restroom, and gets up and leaves me there with her drink. A few minutes later, and I prove (not that there's any proof necessary) where I rank on the autism spectrum: "Hey, so, if you ever go drinking with strange men, especially ones you just met off of Craigslist that evening, you should not leave your drink alone with them, because they might put roofies in your drink. I did not put roofies into your drink, but please go throw it out so I can buy you a new one."

At the time, I'm thinking "O.K., that's it. All signs have been pointing to yes, but that's such a weird thing to say, she's going to be weirded out and want to leave. You blew it, buddy, but you also needed to tell her about the roofies thing, because she's inexperienced with men, and you don't want her to get taken advantage of by the unethical."

She looks at me, and says "nope, that just sealed the deal, let's go back to your place". (It has been years, and I am kind of beginning to figure out why she said that what decided it, but at the time, it baffled me.)

On the walk back to my house, she's awkwardly cute, holding my hand, feeling my arms and musculature, rubbing her hands over the hair on my arms. We stop a couple of times to kiss a little bit, and I explain to her my answer to her earlier question: "So you said, ‘ I would be honored if, as a lesbian, you were even able to be attracted to me'. Well, my post-modern, 4th-wave-feminist brain understands you're 100% a lesbian; you're going to still be a lesbian, I'm not ‘correcting' you or anything. But my Neanderthal brain knows you're a woman. Trust me. I am attracted to you."

We get back to my apartment, I take her upstairs, and she asks to take it slow. No problem at all. I like taking it slowly. We make out, kiss, I slowly undress her. She's nervous, as she said, and we're taking it slowly. She asks me to take the lead, so I do. We start making out slowly, me kissing her all over her face, neck, chest. I kiss her, tease her breasts, suck, lick, tease her nipples, she's making all the good noises, O.K., so far, so good...

I move further south, and slowly start teasing her labia and clit with my tongue. She's whimpering, making the same noises straight girls do, so I figure I'm doing it right... "I didn't know straight men liked eating pussy; I thought straight men hated it." "Well, no, idiots don't like eating pussy; I love it." I continue eating her out, teasing her with my tongue and lips, and slowly start working fingers inside, stroking her g-spot as I flick my tongue over her clit. She sighs, and her hands drift to the back of my head. She keeps whimpering, little noises that generally mean "she's close", so I keep doing what I'm doing. She moans, and says, "how can you eat pussy so well? OhmigodI'mcumming!" (I know not to answer rhetorical questions when your mouth is on a woman's vulva.)

She's smiling at me, giggling, enjoying the glow of the orgasm. I try to keep going, and she pulls me up, saying "sometimes, but usually I'm a one and done girl." She reaches for my penis, grips it, and says "wow, your cock feels so... different in my hand than I expected…" She plays with it for a bit, fascinated by how the skin feels as she strokes it. "It feels so much different than a dildo! I didn't know that."

She starts getting bolder. "I want to blow you." No problem! She takes me in her mouth, and does the best that she can do with sucking a dick when she's never done it before, and it's a great blowjob, because there's no such thing as a bad blowjob.

She slides up, and says "I'm ready for you to fuck me now." I get a condom out, and slide it on, and she lays down on her back. I kiss her, and look her in the eyes while I tease her with the tip. She looks up at me and nods, and says "I'm ready". I slide inside, and her eyes close and she moans.

(In my biased opinion, the sounds a woman makes as your dick enters her are some of the greatest sounds in the world. This was my first time with the doubly-addictive sounds and sights of woman experiencing her first dick.)

I'm fucking her, taking it slowly, as she requests, but as she is getting into it, she asks for it harder, faster, etc. I oblige, and she continues making the adorable little noises that women make; I love the sounds partners make during sex. All of a sudden, she asks me to stop and get off. "Are you O.K.?" "I want to be on top."

Say no more!

We keep going, and it's really cute to watch as she slowly works out the mechanics of it, figuring out how to do it. We're both laughing and having a great time as she figures out how to do it, and now starts sliding all the way up and down, riding like a champ.

After a while she slides off and then lays on her back. "O.K., I want you to fuck me like you'd fuck a straight girl." I raise an eyebrow. "What do you mean? This is how I fuck straight girls!"

She laughs, then looks me in the eye, and says "I'm on birth control, take the condom off…"

Say no more! I slide inside, and she's whimpering again, cursing under her breath, "fuck, OMG, that's what it feels like? it feels so fucking good…" I continue, enjoying her exquisite wetness, and throw her legs up over my shoulders, folding her in half as I fuck her. I'm kissing her, and she whispers "I want you to cum inside of me."

(my brain melts.)

I obliged. We take a break, grab some water, and then we're laying there in the glow, and she's playing with my penis. "How long until you can go again?"

I laugh, and say "it will be about half an hour or so." About half an hour later, she's playing with my flaccid penis, sucking it... "ooh, it's hard again! I want you to cum on my face." "…are you sure? Just so you know, that's not normally what straight people do on the first date." She was sure, so I cum on her face, and she's so excited by it. We lounge around for awhile, I eat her out, we fuck a few more times, really just both enjoying ourselves, and it's late, approaching 2 a.m. I ask her to stay over and have breakfast with me.

She says, smiling, "my wife thinks I'm out drinking with friends... which I am... and now I'm going home with your cum dripping out of me." She had never mentioned her wife before.

That was my first time with her, or any lesbian, but was not my last of either.