[M]y [F]irst-time experience o[F] sex with a lesbian couple

Hey, folks! I posted previously about my first time with a lesbian, period. I figured my first time with a lesbian couple might merit its own, separate post, and I figured this was the place. This one is really kind of two stories in one, so it will be long.

So, as usual, it began on Craigslist Casual Encounters. I was cruising for my typical w4m, and thought… hmm… let's try this ww4m category, what will this be—

I scrolled down through a variety of typical ads with escorts and other poorly-spelled, low-effort attempts by gay dudes to get free dick pics, to find an ad titled something like "Lesbian couple seeks something different".

I opened the ad to read what this lesbian couple was seeking, and how it was different. I quickly learned that they were looking for a man to "get to know", spend time with, and, yes, for sex with one of them. Huh. Intriguing. Well, all right, I'm game. I've already had sex with a lesbian. I'm such an expert!

I wrote a reply, sent it off, thought nothing of it otherwise, and went on to scroll through the rest of the slim pickings that Friday night. Dejectedly, I was about to head to bed when I figured "hey, let me check my e-mail once more."

An e-mail had arrived from them; they like my reply, I seemed funny, write back to us. I did, they replied, we bantered back and forth for a while until they suggested we move to text, which we did. We shot the breeze over nonsense for an hour or so, before they brought up the topic of the ad again. "We're looking for someone who respects that we're lesbians, but will also have sex with her." Sign me the heck up for that, 100%. I respect anyone's sexual orientation.

We banter back and forth over the next week, talking about what they're looking for. Thursday or Friday, they tell me I "passed the test", and we make a plan to meet up for dinner and drinks that Saturday late afternoon; "if you've already made your mind up, just be ready to go for the whole weekend, in case we want to keep you". I'm not exactly sure what that means, but as someone who was never a Boy Scout, I nevertheless believe in being prepared. When I wake up in the morning, I put together some snacks, some male and female condoms, a change of clothes, and of course a towel and a toothbrush. I bounced around through my day and headed out to meet them at the bar.

They both arrived and we grabbed drinks. Rebecca was a Reubenesque redhead, curvy and lush, and Cathy was a thinner blonde; both were gorgeous women (but they're women, so gorgeous is a redundant descriptor). We shot the breeze more, decided to head out to a falafel stand for dinner, and were sitting outside when we really started to get down to brass tacks. Cathy broached the subject: "So, what we're looking for is a man. We want to start with a one-night stand, but maybe we'll keep standing. What you're going to do is fuck my girlfriend while I watch. You're going to be extra-gentle, because it's her first time."

I swallow, and pretend I haven't just heard something normally presented in pornography as if it's the most normal thing (I have since learned much about my naïvete). "All right. That sounds fine with me. You're in charge."
They smile at each other, and there's some whispering back and forth.
"The one thing is," I continue, "you have to promise me this isn't a plot to murder me, because my mother would kill me if that was the case."
They both crack up laughing, and I decide all right, I'll trust my intuition.
Cathy: "Do you want to? You're only going to fuck Rebecca, you know."

"That's fine. Again, I get to have sex with a woman, I'm not turning it down. I'll be quite happy to do my best to make sure she has a great time."

We get in their car, and head off to their place. It's an hour or so drive, and I'm in the backseat. Cathy drives, while Rebecca sits in the back seat with me. I'm not sure what's going to happen, but it's mostly us talking and listening to music. She does sit really close to me and rest her head on my shoulder, while stroking my arm. I occasionally glance up and see Cathy's eyes watching us in the rear view mirror, and she has a huge grin. I shoot her the thumbs-up sign, and she winks at me. O.K., thus far it looks like I'm not going to be murdered.

We get to their place and head inside. We head into the living room and they have me sit down. Cathy asks if I want a drink, and I say yes, because I'm quite nervous. She leaves and comes back shortly with three highball glasses: an excellent, stiff old-fashioned. Delicious. Rebecca and I sit on opposite ends of the couch and nervously make small talk until Cathy returns.

"Let's watch a movie," Cathy suggests. "I want you to pretend I'm not here, and seduce her. Be gentle with her. Remember, she's never fucked a man before." Rebecca is grinning and giggling at this. I look at her, and she blushes and nods. It dawns on me, for the first time, that this is really happening; I'm about to fuck a woman in front of her girlfriend.

We sit on the couch, me in the middle, Rebecca and Cathy each on either side of me. Rebecca sits on my left, which makes it awkward because I'm right handed, but I figure, well, now is as good time as any to learn how to be flexible when making a move. Cathy also snuggles into me, maybe as the alcohol starts to take effect, which is interesting as she had been… not unkind, but had not expressed any interest up until that point. I figure she just wants to be comfortable, and let her drape my arm over her while I threw my other arm around her girlfriend.

As the movie plays, I am rubbing Rebecca's arms gently, and she's giving off these little sighs, more like little peeps, almost, that are really cute. I trace my fingers over her arms, up along the neckline of her shirt, and along her jaw, and run my fingers through her hair. She's really enjoying it, and after awhile she slides a hand down to rest awkwardly on my crotch. This instantly produces the desired effect, and I grab a handful of her hair and tighten my fist, and she whimpers. "Good girl," Cathy whispers next to me, and I start, almost having forgotten she was there. Rebecca turns towards me, grabs me and starts kissing me, and I'm instantly lost. We're suddenly savagely kissing, and she's straddling my lap; she takes off her shirt, and Cathy reaches over and unhooks her bra, and her mammoth tits crash into my face. Smother me, I'm in heaven. Cathy slides out from under my right arm to free my other hand and scoots down further to the end of the couch. I look over at her and ask if she's all right. "I'm fine, you're doing great, please keep going," she says. I ask Rebecca what she wants. "I want you to suck my tits."

Say no more. They're beautiful and huge, the right one is pierced, which I love, and I immediately go to work licking and sucking them. I'm nibbling on one while my fingers is massaging the other, or teasing the piercing, and high-pitched moans are escaping Rebecca's lips. She's running her fingers through my hair. As I'm doing my best to imitate a vacuum cleaner, Cathy's voice drifts over to us. "Tell Mommy what you want him to do, baby."

"...I want him to eat my pussy."

Say no more. I slide Rebecca off of my lap and onto the couch, and kneel on the couch in front of her. I unzip her jeans, and then slide them off of her hips. Her cute thong panties follow suit, and she's sitting on the couch in front of me, stark naked, legs spread. I lean forward and kiss her on the mouth, then slowly trace my tongue down between her gargantuan tits, over the soft rolls of her belly, to her clit. I immediately begin teasing her labia with my tongue, while my fingers gently work inside or her, stroking her g-spot as my tongue alternates between pressing her clit and flicking it. She starts breathing hard and moaning, and I figure I'm doing it's right, because this is the exact same thing straight women do when I'm eating them out.

Cathy's voice whispers right in my ear, I can feel her breath: "Whatever woman taught you how to eat pussy did a good job." I glance over and she's standing over me, watching as I'm eating her girlfriend's pussy. Her dress is gone, tossed over her head somewhere, and she's standing there, stark naked, aggressively stroking her clit while she watches. That… was not in the brochure.

I turn my attention back to Rebecca, as she is making the noises that indicate she's close. I continue licking her clit and fingering her, and am rewarded with the "ohGodohGodOHMIGOD" as the orgasm crashes into her. Her legs tighten and I push them apart, continuing to eat her and finger her as she moans about how good it feels.

Cathy, in my ear again: "It's time to take her to the bedroom."

Say no more. I stand up and grab Rebecca's hand, and my bag from by the door with the other. Cathy leads the way, and I can't help but stare at her tight ass as she walks down the hall. I was promised I'd see one naked woman, and I've gotten to see two; quite the bargain, if I may say so myself.

In the bedroom, Cathy motions towards the bed, and then sits down in a chair close to the end of the bed, obviously positioned there for that purpose. "All right, stud, here's how it's going to work: you're going to fuck her, and I'm going to watch." Sure, this is about what I expected. I strip out of my clothes quickly, and pull out the condoms. I ask Rebecca, "do you prefer a male or a female condom?"

This halts the action immediately. They're both very curious about the female condom, and so I take advantage of the opportunity to talk up their benefits (I much prefer the female condom), about how it's inserted into the receptive partner. "Let's try the female condom!"

With some awkward giggling, Cathy helps her get it inside, and I watch a brief beautiful moment of lesbian domesticity; Cathy sliding her fingers inside her girlfriend's pussy, and Rebecca's face melting as Cathy's teasing fingers slide over her. Then, Cathy motions for me to get to it. I squirt a little bit of lube into my hand, rub it on my cock, and then I awkwardly sit there. "How do you want me to do this?" I ask. "It's her first time, and all…"

"You really going for the good first-time points, huh, stud? Just be gentle with her. Ask her what she wants."

I look at Rebecca for confirmation, and she's nodding. "Just start with the tip."

I slide my lubed-up cock slowly between her outer labia, teasing her with the tip, sliding it gently inside her condomed pussy, just the tip. She's squirming and moaning, talking to her girlfriend, telling her how good it feels, and I'm gently just working the tip in and out. She continues to moan and say how good it feels, and Cathy's talking too, telling Rebecca what a slutty dyke she is, needing to get fucked by a man's cock to properly feel like a lesbian. I slide in and out, each time a inserting it a little more fully, and Rebecca's moaning, begging for me to fill her all the way. Cathy tells me to listen to her, so I slide all the way in. Rebecca's mouth drops open in a silent scream, and then she clenches her teeth and her whole body starts shuddering.

"Are you O.K.? Did I hurt you—" She shakes her head no, and manages to moan between clenched teeth "Nonononono it feels so fucking good, ohmiGOD Cathy his dick feels so fucking good"

"I know, baby," Cathy's voice rasps. "This is why I told you I wanted you to experience real dick."

Rebecca starts to rock her body against mine, moving her pussy to get more of me in her, and begs me to fuck her hard.

"Listen to her, stud. Fuck my girlfriend like a straight girl."

I begin to fuck Rebecca slowly, then faster and faster, and she's getting into it. Her breasts are bouncing and she's squealing as I'm pounding into her. I pull out, flip her onto her stomach, grab her arms behind her back, and starts pounding into her from behind, and her pussy is grabbing my dick so tightly, it's magical. She moans, then screams "ohmiGodMommy I'm cumming", and I slow down to avoid flying over the edge myself. Suddenly, as I'm slowly fucking this woman who is moaning in pleasure, I feel breasts pressed against my back, and it's Cathy. She whispers in my ear: "Are you clean?"

I had been recently tested, and I have always been very judicious in my use of condoms, and I nod. She slithers around and leans down next to her girlfriend whispering, and Rebecca nods. Cathy climbs back over to me while I'm slowly fucking her girlfriend, climbs back behind me, and presses her breasts against my back. She whispers in my ear, her breath hot, "change of plans, stud."

I look at her, inquiringly, and she laughs.

"You fucked her, really well. She's done for a while now. She wants to watch you fuck me."

I broke my rhythm and slipped out, and Rebecca laughs drunkenly and pulls herself up.

What what whaaaat? This was… not in the program.

"Are you sure? You said I wasn't going to… you don't have to feel obligated to, you know… I've had a great time…"

Cathy laughs out loud, and Rebecca does, too.

Cathy says, "This was the test, stud. We wanted to see if you would be respectful of our boundaries, and you passed the test with flying colors. You didn't try and angle it into sex with both of us, you talked to us like people this whole week… I want your dick; I haven't fucked a man in almost a decade."

I practically passed out, and said something like, "hang on, let me pinch myself because I'm dreaming," and they both cracked up.

Cathy. Cathy was… very different from Rebecca. I called for a brief time out to drink some water after finishing up with Rebecca, and to talk with both of them. "You're sure you want this?"

Cathy smiled at me as we all three stood naked in the kitchen. "I've not been sure of something like this in awhile, but watching you fuck her… I want to have the same fun, and I want to show my baby girl how to ride a dick correctly." Rebecca giggled at this, and then almost instantly moaned and breathed in as Cathy reached out to pinch her nipple. Cathy was obviously the dominant one, I had learned, and I wasn't sure how this was going to go, but I was not going to turn down the opportunity that had been presented.

Back in the bedroom, Rebecca sits on the edge of the bed while Cathy and I lay down. I ask Cathy what she wants me to do for her; does she want to be seduced?

Surprisingly, she does. She lies back and stretched her arms above her head. "What do you want to see, baby? Do you want to watch Mommy's pussy get eaten?" Rebecca, wide-eyed, nods her head, her mouth open as she stares openly.

Well, that's my cue. I slide down and she spreads her legs helpfully. Her pussy is already dripping, and I breathe in the delicious scent of a woman's arousal as my tongue meets her clit. Pressing flat against her, I start to gently work her hood with the pad of my tongue while I slide a finger gently inside of her.

A low moan escapes her throat, and she says huskily, "naughty baby, trying to keep this all to yourself. Mommy's going to teach you not be so selfish… do you want that, baby?"

Rebecca must have nodded, because Cathy says "use your words, baby. He can't see."

"Yes, Mommy," Rebecca says. "Please teach me how to share my toys better."

This is pretty fucked up, I thought, as I continued licking Cathy. I am working her g-spot while my tongue dances over her clit, and she continues talking dirty to Rebecca.

"Tell Mommy what a slutty dyke she is for needing a man to eat her out."

"You're… a slutty dyke, Mommy, for needing a man to eat you out."

"Tell Mommy she's bad for making you lose your gold star."

"Mommy, you're bad for making me lose my gold star."

"Come and shut Mommy up with your cunt. Ride Mommy's face."

Cathy is grunting and groaning, and I feel the mattress shift as Rebecca crawls over. I glance up and, sure enough, she squats over her partner's face. I watch her back and see her shivering as Cathy's tongue plays over her clit, and her head lolls as her girlfriend eats her pussy. But I can't forget my job, as it's time to make sure Cathy has an unbelievably good time, too. I continue, working several fingers into Cathy, stroking her, and her pussy is spasming around my fingers, gripping tightly as I stroke inside, tugging gently with the come-hither motion, while I continue eating her. Cathy is moaning, Rebecca is moaning, and then Cathy stiffens and her legs start shaking. I hear her moaning into Rebecca's crotch, while Rebecca is whimpering as she approaches another orgasm. I redouble my efforts, my tongue dancing over Cathy while she pushes hard against my fingers. Rebecca goes over the edge and cums again, moaning deep in her throat, and rolls off of Cathy to lay next to her. Cathy hoarsely says "no more… no more…", and gently slaps my arms.

"Get his condoms for Mommy," she says. Rebecca jumps to comply, and comes back with one of each type. "Put the condom on his cock."

Oh, well. No female condom this time, I'm not going to complain, because this woman desperately wants it, maybe just this one I'll be able to overcome my condom anxiety.

Rebecca is enthusiastic, but obviously not skilled at it, but together she manages to get one open, and her eyes widen as she watches it unroll down the length of my erect penis.

"How do you want it?" I ask Cathy.

"Do you want to watch Mommy ride this dick, sweetheart?" Rebecca nods, her eagerness expressed in the jiggle of her whole body.

Cathy looks at me. "Listen to what my baby wants. Lie down."

I lie on my back, and she proceeds to mount and ride like an absolute pro. At the time, I had no idea as to whether or not her claim of no sex with men in a decade is true, but she made up for lost time with enthusiasm; she would rise all the way to where I was only held in by the barest edges of sensation, and then impale herself on my cock. She rode me slow, fast, and in between, always slowing as my breath would start to catch, before I would even be aware I was about to cum.

"Tell Mommy she's a broken cock-slut, sweetheart." "Tell Mommy she's a bad dyke, baby."

More fucked-up things like this, but I'm not going to question the relationship; Rebecca is repeating what Cathy says with a gleam in her eye, while masturbating furiously.

Cathy is still commanding Rebecca berate her for being a bad lesbian for needing a real dick to cum on, and then all of a sudden she growls "OHMYFUCKINGGODI'MCUMMINGYOUBASTARD" and then leans down and kisses me, which really threw me for a loop, because I had figured she would not be into that, at all. She then looks up at Rebecca and says, "Have I taught you a lesson, baby? Do you know how to share with Mommy?"

Rebecca nods. "Y-yes, Mommy. I can be a better girl. I can share."

Cathy climbs off of me and kneels next to me. "I'm not sure if I believe you. I think we'll have to have you show Mommy again, so she can see if you've learned your lesson, and then Mommy will show you how to share, again."

tl;dr: I stayed the whole weekend.