San Fransisco, Hookers, and My Lesbian Friend [MFF] – PART TWO

POST 2 OF 2 [(PART ONE HERE)](https://reddit.com/r/gonewildstories/comments/mh3m05/san_fransisco_hookers_and_my_lesbian_friend_mff/)

CONTENT WARNING: Sex work, group sex, drugs, alcohol, show business, other fun things like that.

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Me and Melissa smoked another blunt, but I didn’t hit it too much. If what actually seemed like it was going to happen was happening, I didn’t want to be so fucked up that I missed it. Charlotte showed up after forty minutes, and holy fuck was she gorgeous! Like, in an unusual way, but definitely beautiful. And tall. I think me and Melissa both turned into putty in front of the mid-30s woman, which is pretty funny in retrospect. We had about two minutes of smalltalk, then before I knew it she was rubbing her hand on my dick outside my pants.

I didn’t exactly know the procedure, but I didn’t want to stop her. She asked what we were looking for, and I said flat out that my friend had said she wanted to ride a pretty face until she came. Without a beat Charlotte said, ‘we can do that,’ and I swear Melissa got beet red. Without the pandemic none of this shit would ever have happened, but I think it’s put us all in such a ‘fuck it’ mood.

She guided us onto the big mattress we’d laid out in the room. It was a few days slept-on, but clean and unfucked at that point. Charlotte was in a short business skirt with heels, and a white shirt and blazer over her big braless tits. I’d never been physical with a woman that tall before, and let me tell you having someone close to your own size (I’m 6’3″) is a totally different experience. It’s like someone you can really grip with your whole body and just fuck the daylights out of.

I kinda half-spoon this gal, rubbing my cock on her ass through my pants as I touch her back. Melissa’s on the other side, facing the woman, touching her face and neck and sticking her fingers in her mouth. The raw, lusty exploration and eagerness of it was the hottest thing I’ve ever seen in my life, bar none.

I get my hand on Charlotte’s tit, pulling back her blazer off one arm. It’s big and warm, fuller than I’m used to. Melissa unbuttons Charlotte’s shirt, exposing her two big, dark nipples. I’m not sure if Charlotte guided her or not, but either way Melissa’s head goes down and she’s sucking on the same tit I’m fondling while humping from behind.

Then my hands worked down her body, past her waist, until I was pulling her skirt up and feeling Charlotte’s hot, trimmed pussy. I guess I’m not surprised she wasn’t wearing underwear, but at time it startled me. I stuck two fingers inside, excited to feel she was actually wet, and I knew it wasn’t long now before I had to come one way or another.

Around then Melissa came up for air and we took a little breather, all three lying on our sides on the mattress. Charlotte asked to get some water, and got up to go to the kitchen. My heart was racing like a train. I looked at Melissa, way past shame, and said, ‘I’ll wait if I have to, but I’m gonna fuck the shit out of her.’

With almost an animal instinct, I watched Melissa’s hand drop to her own crotch, pressing in between her fat pussy lips through the cloth. I could not believe we were doing this, with each other, in front of each other, after so many years of courtesy and polite conversation. But who the fuck was I to say no at this point? ‘I think we can share,’ she said with a voice I have never heard her use before or since. It was a complete, unapologetic drive to fuck immediately and hard.

Charlotte brought a little thing of lube and a condom over from her purse, where she kept all her escort stuff. Seeing them gave me the sudden fear that I was going to get myself or my friend an STD through our indiscretion (spoiler, we both got tested and we’re totally clean). That worry didn’t last long. Charlotte sat down on the mattress, and both of us were on her like hyenas, grabbing at her tits and her pussy and her clothes. There were a few times that my hand touched Melissa’s in an intimate place, which only added to my excitement. Charlotte put the condom on me, I’m sure to make sure it was on properly, and I watched Melissa watch the process with a certain novel fascination.

‘Oh yeah,’ I thought, and said out loud. ‘You’ve never seen a hard dick in person huh.’ This took Charlotte by surprise, who congratulated Melissa, and asked her if she wanted to touch it. Melissa said ‘I want you to touch me,’ and pulled Charlotte’s hand into her pants.

I didn’t take her disinterest personally. I’m not bad looking, but this woman was fucking hot. And she cost $600. And Melissa was gay, and badly in heat. She pulled her own pants and panties down, not trying to hide anything from me, and knelt over Charlotte before dropping her pussy onto the escort’s face.

It was the image in my fantasies from the past three days come true, but ten times better. I can still see Melissa bending forward, back toward me. Her spine curved and her little waist tensed as she rocked back and forth, moaning, her asshole tensing with each thrust. At the other end of Charlotte, I had her pussy to myself, which somehow was even hotter than having her full attention. I stuck my dick in her, warm and neither tight nor loose, and had my first unbeatable experience of fucking a beautiful woman with a good friend.

This position put my head near her tits, not too far from where Melissa was riding. At this distance, I could smell Melissa, which made it even harder not to cum as I thrust again and again. After just a couple minutes Melissa came, legs quaking, almost shouting. She rolled off of Charlotte, whose face was red where Melissa’s thighs had squeezed it, and lay in a haze with her pussy out on the mattress. I think she lit up a cigarette, but I’m not sure where she got it.

Then Charlotte said something like, ‘let’s get you taken care of,’ to which I said I wasn’t in a hurry. But I did want to take her from behind. I turned her on her stomach, and she lay resting on her elbows as I put my cock in her from the back. With her legs together, it was even better than before. I went slow not to come, groping her tits as I let the wine and pot and experience all flow through me. Then I made eye contact with Melissa. Who giggled like a fool. While she watched me fuck this escort with her pussy out.

‘What does it feel like?’ she kinda mumbled, I think to me. ‘Fucking awesome,’ said Charlotte, beating me to an answer. ‘Yeah?’ I said, kinda surprised to hear that from an escort, and started thrusting harder. Getting off on fucking this woman, and Melissa watching us, was too much to keep in. After a minute, I went as hard as I could, hitting her cervix as I came with a grunt. Then I pulled out, tossing the condom on the floor a few feet away. I collapsed on the mattress, dazed. Then Melissa started to play with Charlotte’s pussy, stroking it right where I’d been moments before. ‘Fuck me with this,’ Melissa said to her, and she handed her some kind of dildo shaped vibrator I’d never seen before.

Charlotte took a little lube and started to slide the vibrating toy in and out of near-catatonic Melissa. I walked pantsless to the bathroom to piss, and admired my sweaty hair and post-cum cock in the mirror. I said something insufferable like, ‘you’re the fucking man,’ which I hope can be forgiven under the circumstances.

I came out of the bathroom and put on some music, I think The Strokes. I loved the thought of Melissa seeing my cock, but I think she was a little preoccupied with cumming again. After the second one she pretty much fell asleep on the spot. I lay on the other side of Charlotte, who chatted with me as I fondled her tits. She talked about food, and the stimulus, and some of her friends making OnlyFans. I’m glad she was comfortable, but honestly it was all very surreal to hear in the moment. After maybe ten minutes, she sucked me off, nice and slow. I ran my hand through her silky hair as her lips went down, and her tongue and throat touch the head and underside of my cock. It was The Strokes, I remember now, because Julian Casablancas saying, ‘I just lied to get to your apartment.’ Or whatever it is.

I came in her mouth and she swallowed it, smiling, as I nearly drifted off. It’s a wonderful feeling. Probably the best in the world. I looked over at Melissa, covered in a sheet but still very much exposed with her pants around her ankles. What a crazy, fucking wild world of surprises, I remember thinking. I paid Charlotte, tipped, thanked her politely, and walked her out to her car in a pleasure haze. The smell of smoke and sex hit me hard when I came back in. I remember brushing my teeth, then letting my pants and underwear fall again — maybe on purpose. Then I crawled beneath the sheet and joined Melissa in sleep.

We woke up the next day sluggish and proud of ourselves, if a little shocked. ‘We need to take it easy for a little, or who knows what’ll happen,’ she said, as if chastising us for going so hard. I didn’t want to say the wrong thing, so I kept my mouth mostly shut, but I cleaned up with her and went about another afternoon of work. The disparity between our days and nights had only grown.

I couldn’t stop thinking about her ass. It was like an obsession, like Tantalus, the closer I got to it the more I couldn’t have it. I felt so spoiled. Why couldn’t I just be grateful for what had happened? I wasn’t catching feelings, I’m sure of that, but I kept eyeing her throughout the day with more and more intensity. What I’d seen could not be unseen.

We tried to play it clean and sober that night, the last one before we flew back. We took the sheets to a laundromat, ate a respectable pussy-free dinner, and watched a Bergman movie on her laptop. Then we tried to turn in early. Big mistake. We tossed and turned for a couple hours on our phones, chatting occasionally. Then I shut my eyes and went into the fantasies of my mind. I must have seemed pretty asleep, because twenty minutes later I heard an unmistakeable sound — her dildo vibrator, quietly purring under the comforter.

I froze. Not sure what to do. I tried to feign sleep, but made a strange noise, and in that moment she gasped and turned it off. I inhaled. Then I stood up and walked to the kitchen for some water, my dick making a huge tent in my loose basketball shorts. Streetlight through the window was the only light. I drank the water, then walked back, climbing in to mutual breathless silence in the dark. I really had no idea where we stood.

‘Are you hard?’ she whispered to me. I swallowed. ‘Yeah,’ I said, fake casual. What the hell else was there to say? We’d already banged the same woman.

‘Can you fuck me?’ she asked. It took me a second to even understand what she meant.

‘Uhhh. Yeah.’ I said. My heart was fucking pounding at this point. ‘Are you sure you want that?’

‘Yeah.’ She said. ‘But you can’t tell anyone we know.’

I guess she had her lesbian reputation to uphold. Understandable. As they say, it was an honor just to be nominated. Somehow in disbelief again, I decided to savor ever moment, and do it right. ‘Get on your knees,’ I said, now in a voice I’d never used before. I heard her gasp a little. Then she obeyed, rolling onto her stomach and pushing her thick ass up in the air. I felt her shaking a little as I pulled the elastic of her pajama bottoms down.

I put one hand between her legs, slowly, feeling her curly haired bush and soft, warm pussy under her panties. I felt like I was in an Amazon realm. Slowly, I worked my way up her body, the first man to tread this or that ground as I cupped her soft tits. My cock was pressed against her ass crack now, through my loose shorts. I slipped her panties down, shivering, and nestled the head of my cock into her vulva.

It was the softest, warmest, sweetest thing I’ve ever felt in my life. She was the perfect tightness, almost ridged a little it felt like. I’m pretty big, so with most girls I fuck I hit the cervix with an inch to go. It’s just a sad fact of life that most girls have short pussies. But here, I could go the full distance. My dick slipped inside her, going until my balls rested up against her warm pussy lips and bush. I throbbed, and she gasped as I filled her out. ‘Holy shit,’ she whispered the first time I pushed in and out, which made me feel like a goddamn rockstar. ‘Holy fucking shit.’

I got a good two handed grip on her tan ass, slowly fucking my friend from behind as she moaned. After a thirty seconds, she shifted, and I paused. ‘Don’t be gentle,’ she said.

I did as asked, pushing her down onto the mattress so my pelvis pressed into her thick ass as I fucked her. I put my nose in her hair, smelling her pomegranate conditioner I’ll never forget, and put my arm around her neck in a semi-chokehold as I dicked her hard.

I was sleepy, so my sensitivity was a little low. I pounded for easily five minutes, just building a consistent rhythm and listening to her moans. Then all of a sudden her pussy gripped me crazy tight. She jerked, almost like a seizure, and gasped in a sort of shock as I kept fucking her harder. Then more wild moans and curses. Clenched tight, I kept thrusting, and the only words I said were ‘You’re on birth control?’ to which she nodded. (She says it’s for her acne and period pain, but maybe she secretly fucks dudes all the time. I personally doubt it, but who knows.)

As soon as she nodded yes, I pushed deep and pumped a huge load inside her. Another small step for mankind. I lay there, reveling in the moment, and smelled her sweaty hair once again before pulling out (to another moan) and rolling over.

‘Thanks,’ she said to me, laughing a little. It was this almost indescribable mix of innocent friendship and deep instinctual lust. ‘Wow. Now I now what that’s like.’

‘Good?’ I said. She nodded, and was asleep with my cum still inside her no more than three minutes later.

The location scout was a success, by the way. We flew back to LA the next morning, and our 1st AD apologized for booking more days than were needed, ‘just to be safe.’ I assured her we filled the time, and it was nice to catch up with Melissa. The shoot went great, and it was fun to film in a space where I’d just fucked the daylights out of my lesbian producer. Now, whatever model or actress she has on her arm the next time we get drinks, I’ll have a slightly easier time knowing where she’s coming from.

Source: reddit.com/r/gonewildstories/comments/mh3nos/san_fransisco_hookers_and_my_lesbian_friend_mff