Trans Madison Surprise Cock Reveal

[Author's note: This is my 100th story on Literotica. It's been quite a ride and I look forward to sharing more naughty stories with you. This one was inspired by a reader who had a fantasy about being seduced by a trans woman. Hope you enjoy!]

I felt good heading into the bar that night. I was newly single and, in my late twenties, felt like I could get back into the dating scene. I'd spent time making sure I was presentable. My six-foot frame fit well into my travel pants and a blue satiny shirt complimented my fairly muscular frame well. My brown wavy hair fell just right and helped accentuate my very blue eyes. Was I a catch? Can a guy be a catch?

"You've got this, Brent!" I said out loud, trying to give myself some courage.

Though I thought I was prepared for just about anything - that "anything" turned out to be a sexual adventure I never saw coming.

I'd never been to this particular bar. Crowded, lively, and upbeat -- the place was filled with all kinds of people. I saw men and women cuddling in side booths, gay couples holding hands and even what may have been a trans couple kissing. It reminded me that I'd fantasized about having sex with a trans woman, but never thought I'd act on it.

As I scanned the room, two women stood out. Both seemed near my age. It was something in the way they interacted with each other -- a tenderness and yet a hunger. Were they gay or just friends? I couldn't tell. The woman on the left was African American, her skin a lovely shade of brown with long straightened black hair. Her dress was amazing. It was so tight that it accentuated every curve of her waist and the shape of her large breasts. I could even see her areola and nipples poking through.

The other woman was blonde with slightly smaller boobs and slender legs, long hair falling down her back. As I slowly made my way to the bar, she looked at me. Her piercing blue eyes sparkled, her face friendly and open. She smiled shyly at me and looked back to the other woman.

I played it cool. I stepped up to the bar near them but didn't look over. The bartender offered me a beer, and I accepted.

"There's a free stool here," the woman on the left said. "If you want to sit. I don't see anywhere else."

She was right. The place was packed.

"Thanks," I said, pulling out the stool next to the blonde.

I looked forward, suddenly unsure of what to do.

"Simone," she said.

I turned and the first woman was extending her hand.

"Nice to meet you," I said, taking it. Her hands were soft and tender. "Brent."

"And I'm Madison," the other woman said with a light feminine voice.

I took her hand too and was struck by her beauty. Her face seemed so kind and gentle. I tried hard not to look lower but noticed her cleavage -- two gorgeous globes. As I looked down at her hand, I saw two nipples protruding from her chest. I quickly looked up into her eyes, which wrinkled slightly. She seemed shy, yet there was something else there -- an interest?

I let go of her hand and she turned to Simone and giggled. "He has soft hands. That's good."

I laughed. "No one's ever described my hands as soft."

"There's a first time for everything," Simone said. Her voice was lower, more sensual.

While Madison was a blonde beauty, Simone was a sultry siren. When she smiled, the corner of her mouth turning up slightly and her eyes almost winked at me. I'd come here to meet people. I hadn't expected to be sexually attracted to the first two women I met.

Madison wore a red skirt that came down to her knees, and a silky black top that hugged her ample figure. Simone's dress rode up so high that I could see her black panties. She made no move to cross her legs as she sat on the bar stool. I caught her eye as I looked up. She smiled again.

"So ... Brent," Simone said. "How's the food here? This is our first time."

"Oh ... mine too," I said.

"Then I guess we'll explore it together," she said, picking up a menu and handing it to me.

I was a little nervous for some reason. Sitting next to such beauties was throwing me. I could have sworn there was more to what Simone was saying than just exploring a new restaurant.

"The prime rib sounds good," I said.

"I do love a rare piece of beef," Simone said.

Madison giggled and looked at me. I felt my face turn red.

"I'll have the salmon salad," she said, looking back at the menu.

The bar tender took our orders: two prime rib dinners and the salad. A booth opened up and we took it. It had high walls on three sides, so it felt very private. I sat between Simone and Madison, each of us on a side of the small table.

"Gotta say. That was really good," I said as I finished my meal.

"Mm mmm," Simone said, only halfway through hers. "I'm saving room for dessert."

The double-entendres were flying by, and it was making my head spin. Were these women -- Simone in particular -- coming on to me or just having fun?

"So ... what's your story?" Madison asked me, setting down her fork.

"Not much to tell, really. I, uh, am recently single. Just putting myself out there."

"I, um, am kind of too," Madison said.

"How so?" I asked.

Simone reached out and took Madison's hand. Madison looked up and Simone leaned over the table to kiss her blonde friend. It was not a kiss between friends, that's for sure.

"Oh," I said, surprised. "You two are together?"

"We are," Simone said, breaking off and sitting back down. "We're lovers, but not exclusive. We love being with other people too."

It was something in the way Simone said that last part that got my dick tingling. I started picturing these two, naked in bed, Simone's mouth and tongue on Madison's pussy. I had to shake my head to break free of the fantasy.

"So ... getting out there?" I asked.

"Simone has been my mentor of sorts," Madison said, turning to face me. "She helped me come out of my shell and really be myself. It's been wonderful!"

The two intertwined their fingers across the table. "She says I need to meet more people. Get to know them. Broaden myself."

"Ah," I said, not at all sure what that meant.

Another round of drinks interrupted us. We raised our glasses and turned to lighter subjects as the alcohol loosened us up. I learned more about this couple and they in turn got my backstory. The girls headed to the bathroom at one point. I shook my head as I contemplated this strange situation.

As they returned, I noticed them giggling and smiling at me, Madison nodding her head to something Simone whispered in her ear.

"What's the joke?" I asked a bit incredulously.

"No joke," Simone said, sitting down. "But we do have a question."

"Anything," I said.

"Do you like us?" Simone asked, her hand touching my knee, sending tingles all through me.

"Uh, sure," I said. "You guys are great. It's been nice getting to know you."

"We feel the same," Madison said, putting her hand on my thigh. "We, um, were wondering if you might want to get to know us better. Really better."

I saw a hopeful look in Madison's eyes, yet also an uncertainty. Was I being propositioned?

I took in these two beauties sitting next to me. I had not planned on anything other than good conversation on my first night back on the single scene. My dick was telling me that I should say yes. I felt it rising in my slacks. I wondered if the girls noticed too.

"I'd love that," I said, looking between them.

The next thing I knew, both of their hands had moved from my legs to my crotch. I nearly jumped at the shock and felt sharp pleasure in my dick.

"I think he does like us, Madison," Simone said, her fingers kneading my cock while Madison played with my balls.

"Mm," I said. "I guess we don't need a dessert menu."

"I think there's a wonderful dessert waiting at my place. If you want to come," Simone said. I caught the double entendre and liked it.

"I'd love to come ... over," I said.

We all got up from the booth and headed to the door. Simone gave me directions to her apartment, and we split up.

Driving over, I had to remind myself that this was really happening. It looked my first night dating would be my first threesome ever. The thought got me very aroused.

Simone lived on the top floor of a very nice apartment complex. I followed the two women up the stairs and inside. I could see a spacious living room beyond us, but my attention was immediately drawn back to Simone and Madison, who had started kissing, sending tongues back and forth between their mouths.

"Come on in," Simone said as they broke off.

They each grabbed one of my arms and ushered me further into the space. We stopped in the middle of the living room and I felt their arms wrap around my waist. I turned towards Simone, and she lifted head up slightly, opening her mouth, her tongue licking her full lips. I tilted my face down and our lips met. I felt the smoothness of her lips and the wetness of her tongue as it glided across me. I opened and let her explore.

"Mm," I moaned, kissing her back. "Your lips feel amazing."

I turned to Madison, a little taller than Simone, but still several inches shorter than my 6'1". She smiled and brushed some hair away from her face. Coming in, we kissed. It was gentle at first, her lips equally as soft and inviting. I initiated a meeting of our tongues and felt Madison eagerly respond.

Her hand went lower on my back, caressing my hips, squeezing one of my cheeks. No one had ever done that to me before. It felt great.

"You know, I never expected something like this to happen tonight," I said, breaking off.

"Us either," Madison said, "I haven't ever done anything like this -- going to a bar and meeting someone to bring home and have sex with."

"Oh, I have," Simone said, smiling and coming back in for a French kiss.

I put my arms around each girl's waist and pulled them in close. Soon we were in a three-way kiss -- my first. The feeling of three sets of lips and three tongues swirling and touching and licking -- was incredible and was getting me very aroused.

"Let's sit," Simone said as we broke off.

We went over to the couch and kicked off our shoes. I sat between Simone and Madison. I turned to kiss Simone and felt Madison's hand on my crotch. I reached up with both of my hands and ran my fingers across Simone's nipples. They popped to attention.

"Oh!" Simone gasped, looking down. "Shit, Brent. That's awesome. More, please!"

I cupped her large breasts and squeezed them.

"Mm!" Simone purred.

I felt her hand join Madison's on my dick.

"You're getting really hard," Simone said.

"I'm getting very turned on!" I said.

I let go of Simone's boobs and turned to Madison. I could see her nipples clearly. I touched them with my fingers, squeezing them gently.

"Oh ... mm," she moaned and came in for a kiss.

As my tongue entered her mouth, I cupped her breasts, pushing in on them with my palms. Madison lifted her chest in response.

Moments later, I felt hands tugging at my belt, undoing it. It was Simone. I broke off with Madison and watched Simone undo the button at the top of my pants and unzip them. My dick bulged out in my underwear as she ran her hand along its length.

"Lift up a little bit, Brent," Simone said, pulling on my pants.

I lifted myself up and felt her pull down my pants and underwear. My dick sprang out, standing straight up as the pair pulled my things all the way down and off me. Two sets of hands grasped my rod as the pair came back in for a three-way kiss.

I felt my pelvis moving up and down to maximize the feeling of them gripping me. I turned and kneaded Simone's breasts, feeling their weight through the thin satiny fabric of her dress.

"You look nice," Madison said.

I turned to see her staring at my dick.

"You're shaved."

I nodded. "I heard most guys are doing that now. It feels nice too."

"Can, um, I feel it?" she asked gingerly.

"Of course!" I said.

She reached out and touched my dick, sending shivers through me.

"Go ahead and squeeze it," Simone said. "He'll like it."

"I don't have much experience at this," Madison said.

She grasped me and squeezed.

"Oh, Madison. That feels really good."

"It does?" she asked.

I leaned over and kissed her, letting my hands fondle her breasts. I could feel her nipples respond to my touch, getting harder and longer.

"It'll feel really good in your mouth," Simone said.

I looked at Madison, who seemed hesitant, her hand still squeezing me and moving up and down my dick.

"Can I?" she asked me. "Can I suck your dick?"

"I want you to so bad!" I said, pushing some of hair away from her face.

She leaned over and kissed the head of my dick. "I've only done this one other time," she said.

Simone leaned down next to Madison. "You'll do great. Just open and take him in, like with Kiley."

"Kiley's the other guy you've been with?" I asked.

"Sort of," Madison said.

I watched her open her mouth. Her tongue flicked out and licked the head of my cock.

"Mm," I said.

She opened more and I felt this warm wetness as the head and some of my dick slid into her mouth.

"Oh, fuck, Madison. It feels so good to have me in you!"

That seemed to encourage her. She pulled back, opened wider, and plunged back down on my member.

"Oh!" I gasped at the wonderful tingly feeling it gave me.

She got most of me inside her mouth, pursed her lips and sucked in, pulling back up. The pressure on my dick was incredible and sent pleasure all over me.

"Shit!" I said. "Oh, that's good!"

Simone joined Madison and they took turns. One of them would suck on me while the other played with my balls and licked the base of my shaft. I watched them kiss each other as their tongues played across the head. Simone added a twisting motion with her closed fingers squeezing me. It was amazing to watch these two gorgeous women go down on me.

"I can't believe you guys are doing this. Oh ... mm."

The two licked up and down the length of my dick and I heard slurping sounds as their mouths came off sucking me.

"I bet you can take it all in," Simone said to Madison as she held me firmly in her grip.

"You think?"

"Uh huh. Just open wide and relax your throat. I know Brent will like it a lot!"

Madison stared at my cock for a moment, then looked up at me. I smiled and nodded. She opened her mouth and went down on my cock -- down and down and down until the whole thing disappeared into that warm wetness. I don't have a super long cock -- probably a little over six inches, which made it a little easier to swallow. She'd done it!

"Oh, fuck, Madison. Oh ... suck me ... suck me!"

She came up and went back down all the way. My ex had given me blow jobs, but never like this. I was getting super aroused.

"My turn!" Simone said.

My cock popped out of Madison's mouth and Simone went down on me, swallowing my entire cock and bobbing up and down.

Madison came up and we kissed. "Did you like my dick?"

She nodded. "I love how soft your skin is but how hard it was underneath. I like sucking cock!"

We kissed gain and I kneaded her breasts.

"Do you want to take your top off?" I asked.

She hesitated for a moment, then pulled the fabric from under her skirt. I helped get the blouse over her bosom and over her head. Underneath, she wore a black bra -- thin fabric that let her nipples show through.

I ran my fingers across her nipples, flicking them back and forth and squeezing them between my index finger and thumb.

"Mm," she moaned as we kissed.

I moved down and kissed and licked her neck. Moving down further, I kissed the place between her breasts.

"Oh. Yes. Oh," she moaned.

"Let me take this off of you," I said, reaching for her bra.

She twisted so her back was to me. I managed to get the clasp undone, though I didn't have much experience in that area. The bra fell to the side. When Madison faced me, I beheld her boobs.

"Wow!" I said, admiring her.

"Do you like them?"

"I sure do," I said.

I cupped her two glorious globes, topped with light-colored areola and large nipples.

"I love that," she said softly.

All the while, Simone was licking and sucking on my dick. I started lifting my pelvis up and down to match her rhythm.

"Do you want to lick my tits?" Madison asked, cupping a boob and offering it to my mouth.

I leaned over and touched the end of my tongue to her hard nipple.

"Mm," she purred.

I sucked in.

"Ah!"

I flicked my tongue back and forth while my fingers tweaked her other nipple. Her chest rose towards my mouth and her pelvis started rocking back and forth.

I started to reach between her legs, but she stopped me. "Not yet. Not yet."

I could tell Madison was a shy girl and I was in no rush. This night had already gone way beyond my wildest expectations.

I continued to suck and tweak Madison's nipples.

After a few minutes, she bent over and took another turn on my cock. Simone came up and offered me one of her large breasts. I took a nipple into my mouth over her dress.

"Oh ... fuck yeah," she said.

As I pulled back, I could see I'd made a large wet spot on her dress. The fabric was so thin that the bumps on her areola showed through. I took the other one in my mouth. Simone started moaning and holding me to her chest.

I reached down between her legs, and she opened. I touched her crotch and felt her panties -- dripping with moisture.

"I'm so fucking wet for you," Simone said as she moved her hips, pushing against my fingers.

I brought my fingers up and sniffed her aroma. She took my hand and put two of my fingers into her mouth, licking her juices.

"You love to taste yourself?" I asked.

"Mm hmm," she said. "You'll love my taste too ... soon!"

Madison continued to suck my dick. It was turning me on so much that I was afraid I might have to ask her to stop. As it turns out, she stopped on her own.

"Let's get the room ready," Simone said to Madison.

The blonde beauty helped Simone pulled on a lower couch cushion, transforming it into a bed.

"Clever!" I said.

"Do you want to get Simone out of this dress?" Madison asked.

"Do I ever!"

Simone stood and together, Madison and I pulled the tight fabric over her lucious body. The three of us kissed, then Madison and I together removed her black bra. Her big boobs sprang out and her nipples bounced slightly -- sticking straight out from her chest.

"Wow!" I said. "You've got such great tits!"

"I bet your mouth would love them too!" she said, holding out a breast to me.

I eagerly took one of her large dark nipples into my mouth, sucking and licking. I noticed Madison taking the other, and together we sucked and licked and flicked.

"Oh ... fuck, guys. Shit!" Madison said, watching us.

I reached over and squeezed one of Madison's butt cheeks. She smiled at me, her mouth full of nipple. I knelt and kissed Simone's mound, tasting her juice through her sopping panties. It was tangy and salty -- delicious!

"I want you out of these," I said, tugging at the hem of her panties.

She helped me and shrugged out of them. I was inches away from her dark labia and shaved mound. Moisture dripped from her pussy lips, and she pulled me towards her. I licked off a drip of moisture and tasted her fully.

"Oh!" she moaned. "Lick me, Brent!"

I used my tongue to lick up her slit, getting a lot of juice on my tongue and in my mouth. She shuddered with excitement as I drove my tongue into her clit.

"Oh ... ah!" she moaned, holding my head to her crotch.

I jerked my dick to keep myself hard. Madison must have seen me as she got down and started kneading my cock, then sliding it into her wet mouth.

"Oh!" Simone moaned as I drove my tongue into her pussy, tongue-fucking her. "Ah ... ah ... ah!"

She held her pussy lips open to give me even better access. I licked up and down her slit and took her hard clit into my mouth -- biting on it gently and sucking it into my mouth and twirling it around on my tongue.

"Oh ... ah ... oh!" she moaned, her hips moving in and out, in and out.

"I think his cock is ready for you," Madison said, coming off my dick.

"Shit ... I want it so bad!" Simone said.

"Turn around," I said. "I want you to make out with Madison while I fuck you from behind!" I said.

"Ooh! I love it!" Simone said, turning and getting on her knees. Madison crawled up on the edge of the bed and spread her legs so Simone could come in close. I still couldn't see whether Madison was wet like Simone, but I knew I'd soon experience making love to her as well.

Simone began licking Madison's nipples as I came up from behind. My dick was already wet from Madison, but I moved it up and down on Simone's slit. This was it. I was about to have my first fuck since the breakup. I was so turned on!

"Are you ready for me?" I asked.

"I want your cock inside my pussy, Brent!" Simone said, turning back. "Madison made it so hard. I can't wait!"

I held my dick up to her pussy and pushed gently. Her labia opened easily, and the head of my cock disappeared into her love hole.

"Oh!" Simone sighed.

I pulled out and saw the head of my dick was coated with clear liquid. I pushed it back in, separating her lips and opening her pussy. I slid in about halfway -- feeling warmth, wetness, and a pressure over my entire cock.

"Oh, fuck!" Simone said. "Fuck me, Brent. Go deeper!"

I pulled out a little, then pushed back in. My rod slipped into her tight pussy all the way to the base. I felt huge tingles all over my body and especially on my shaft.

"Feels ... oh ... so good!" Simone moaned.

"Your pussy is so tight," I said.

"Do you ... like it?"

"I love it!" I said, pulling out and pushing back in.

I held her butt cheeks and pushed her ass away from me, watching my dick emerge, then pulled her close, shoving myself back deep into her recesses. It felt wonderful!

Simone continued suckling Madison's tits. Madison held Simone's head to her chest and watched me closely as I fucked her friend, licking her lips as our eyes met. That got me even more turned on.

"Faster ... more!" Simone moaned, breathing faster. "Make me cum on your cock, Brent. Make me cum!"

I increased my pace, pulling out and going back in quickly and deeply, my pelvis slapping up against her ass. My dick made a slurping sound as it moved in and out of her wet pussy.

"Oh ... oh ... oh!" Simone moaned as I fucked her. "Ah ... oh ... I'm ... oh ... here I ... AHHHH!"

I felt her pussy contracting and expanding on my dick. She was cumming! I nearly came myself but managed to hold on, pushing my dick in as far as I could and hanging on as she convulsed and cried out.

I slowed my movements in and out, realizing I was sliding back and forth even easier. I pulled out and saw more liquid dribbling out of her hole and onto the head of my dick.

"Oh, Brent!" Simone said, getting up on her knees and turning to kiss me. "That felt so good!"

"I'm so glad!" I said. "Your pussy felt so good on my cock that I almost came!"

"Ooh, I'm glad you didn't," Simone said. "I want you to fuck my ass. Have you ever done anal before?"

I shook my head. It had never come up in my prior relationships. But I was now curious. Very curious.

"You like that?" I asked.

"I love it!" Simone answered. "We both do."

"Oh!" I said, looking at Madison.

She smiled again. "I want to see you put your cock into her asshole."

"Grab the lube, okay?" Simone said.

Madison leaned over and opened a drawer of the couch's end table and pulled out a tube. She handed it to me.

I squeezed some out on her tiny dark rosebud, then spread more on my very hard dick.

"Rub it around my asshole and inside too -- open me up so I'm ready for your cock!"

I used my thumb to push the lube into her ass, twisting around and pushing in deeper. I could feel her relaxing the muscles there.

"Now, Brent. Fuck my ass," Simone said, holding her butt cheeks open and spreading herself more.

I put the head of my dick at her ass and pushed. It was much harder to get in than a pussy, but I pushed again, and the head of my cock went past her asshole and inside her.

"That's right. Oh, yes. More ... more."

I pushed in further and felt the tightness of her ass clinch my dick. I pulled out a little then pushed in further until my entire rod was all the way into her asshole.

"Mm ... oh ... fuck me!" Simone moaned, pushing back against my cock.

It felt very different than fucking a pussy. It was warm inside and her asshole really clamped down on my cock, giving me incredible feelings of pleasure as I pulled in and out.

"It's incredible!" I said, holding her nice round butt cheeks and slamming my cock home over and over again.

Madison held Simone's face and watched as I fucked her ass.

"You're going to love his cock, Madison," Simone said, breathless.

"I want it so bad," Madison said, then looked up at me. "Will you fuck my ass too? I want your cock to be inside me!"

"I can't wait!" I said. "I want to fuck all your holes!"

"Simone," Madison said. "I can't stand it anymore. I've got to show him!"

"Show me ... show me what?" I said, still pounding away.

Simone turned her head towards me. "Get ready for a big but pleasant surprise, Brent. Keep fucking me ... keep going, okay?"

I nodded, confused but curious.

Simone reached up and pulled on the hem of Madison's skirt. Madison lifted her butt a bit and let Simone pull it off. I saw her panties for the first time. She had a large mound, and I was getting really turned on in anticipation of seeing her pussy.

I could see Madison's narrow waist as Simone grasped the hem of her panties and pulled down. What I saw next shocked me so much I stopped fucking Simone's ass. What emerged from her panties was not a wet pussy but a hard cock that seemed to jump up from between her legs.

"Shit!" I said without thinking. "What the ...?"

I looked up into Madison's eyes. There was some guilt there, but also relief. I saw her hand reach down and grasp the rod and stroke it. It was huge - bigger than mine. Her pubes were shaved bald, her white skin practically glowing as tiny bits of liquid dripped from the head.

"Why ... why didn't you tell me?"

"It was my fault," Madison said. "I'm still new to all of this -- to who I really am. I'm sorry if I shocked you."

Simone kissed Madison's knee and gently pushed back and forth on my cock, sliding it in and out of her asshole. "Isn't she beautiful?"

It was true. I saw Madison completely nude. Her blonde hair and kind blue eyes framing a tender face -- her good-sized boobs, slender waist and legs -- with that large cock sticking straight out towards me. I was mesmerized.

"I am ... shocked," I said. "I've never seen an erection in real life, other than my own."

"Do you like it?" Madison said, squeezing delicate fingers around her rod and pulling down towards the base.

"I, I don't know. You look so beautiful -- so feminine. Your gorgeous body and tits -- and then -- your cock. It's so big!"

"I know," Madison said, running her fingers across the head. "I changed so much when I transitioned -- but my dick didn't get smaller. It's one of the reasons I've been so shy about all this. I'm different."

"Different -- and wonderful!" Simone said.

I don't know what it was exactly, the sight of Madison's girl-cock or the feeling of Simone's asshole fucking my dick -- but I was getting more turned on. I started moving in and out of her ass again.

"You know what's even more wonderful than how her she-dick looks," Simone said, "is how it tastes!"

Madison held herself out to Simone who opened and swallowed her ladystick.

"Oh ... fuck!" Madison gasped.

The sight was incredible -- a beautiful woman sticking a large cock inside the mouth of another beautiful woman. I found myself getting aroused and fucked Simone faster.

Madison had her eyes closed. She opened them and looked right at me. "Would you ... Brent? Would you suck my she-dick?"

My eyes got wide, and I stopped fucking Simone. For some reason, my dick got even more turned on as I thought about it.

"I've, um, I've never done anything like that," I said.

"And I've never had a man suck my cock either," Madison said.

"But ... Kiley?" I asked.

"She trans like me."

"Oh!" I said, still trying to wrap my brain around what I was seeing.

"I know you'd love it," Simone said, coming off Madison and moving forward off my cock.

She moved out of the way and there I was -- on my knees, only inches away from her incredible erection. I could see how aroused she was. Her dick throbbed and bounced slightly. I could see the vessels along the length were engorged and she held herself out to me.

"Please suck me cock, Brent. Please open up and take me inside you. I want to feel your tongue on me. I'm so turned on I can't stand it!"

I moved forward. I'd never in a million years thought I would suck another cock. But Madison was so much a woman -- so beautiful and magical. She possessed something most women don't.

I moved my hand closer. Madison took it and placed it gently on her lady part. I felt the softness of her skin and the hardness of her erection. I gently caressed her.

"Mm ... mm," she purred.

I leaned forward. Her pelvis moved towards me. The head of her cock was only an inch away. Should I take this step? I didn't consider myself gay, but this didn't feel gay at all -- but something much more.

"Your cock is beautiful," I said, "just like you."

"Thank you, Brent. Thank you!"

I leaned in and kissed the head of her dick. It felt very soft and squishy.

"You've got such a big mouth, Brent. I bet you can take all of me. Take all of me -- please!"

Simone gently rubbed my back as if to encourage me to take the final step. I opened my mouth and enveloped her cock, letting it slide into my mouth. I was surprised how smooth her skin felt and how cool.

"Oh ... so warm ... so wet ... I can't believe you're doing this!"

I couldn't believe it either. I let her dick go in deeper and deeper, across my cheeks, across my tongue, feeling the head burrow deeper into my mouth. I sucked in and put pressure on her from all sides.

"Oh ... fuck ... oh!" she moaned. "That feels so good. Fuck!"

I pulled out, pursing my lips and sucking in with my mouth. She felt so hard. I let her pop out of my mouth and then went right back down on her. I was sucking her dick!

"Oh ... ah ... oh," she moaned, holding my head and urging me on. "Simone ... his mouth feels so good!"

I was having a bit of an out of body experience as I went up and down on her dick. It was new -- and exciting. My dick was feeling very aroused.

"Let me fuck your mouth, Brent!"

She stood, her cock standing straight out from her body. I opened my mouth and let Madison fuck me. It felt strange at first as she thrust in and out of my mouth rapidly. I pursed my lips on her cock.

"Oh ... shit!" she exclaimed. "Oh ... fuck!"

She started panting and just when I thought she would cum in my mouth, she withdrew.

"I almost came!" she said.

I stood and faced her. "I can't believe I'm saying this, but that would've been all right."

We kissed, our two dicks rubbing against each other. As we made out, I kneaded her breasts. Simone stood next to us and grabbed both our cocks, gripping both of them with her hand and rubbing back and forth.

"I want to try something, if you're game," Madison said, breaking off.

"Well, I just sucked my first dick so ... I'm open!"

"Fuck me."

"Fuck you?"

"Fuck me with your cock up my ass. I watched you fuck Simone, and I want you inside me."

I looked in Madison's face. She was hungry for me, I could tell. Her hand joined Simone's on our two dicks. I felt tingling as the two stroked us. I looked at Simone, who nodded.

"Be my first man cock," Madison said.

"I will," I said. "How do we ...?"

"Just sit on the edge," Simone said.

Madison moved out of the way, and I sat. Simone grabbed the tube and slathered it all over my dick. Madison bent over away from me and Simone got her wonderful little rosebud all slick.

"Remember to relax your muscles," Simone said, guiding Madison to me.

She started to sit on my lap. I held up my dick and Simone positioned Madison's ass, so it touched the head. As she sat down, my cock slowly disappeared into her. Her ass clinched my dick, and I could feel me slithering up her hole.

"Oh ... shit!" Madison said as she sat more. "Oh ... you're fucking me. Shit!"

She sat down completely, squirming a little side to side.

"You feel so great," I said. "Your ass is wonderful!"

Madison lifted up her legs slightly and I watched my dick emerge from her ass. As she sat back down, I felt tightness travel up the length of my stick.

Simone knelt and started sucking Madison's girl dick. As Madison raised up, her cock came out of Simone's mouth and my dick came out of her ass. As she lowered down, we were both swallowed up in mouth and ass.

"You guys look awesome!" Simone said, coming off Madison and jerking her off, using her spit as lubrication.

"We better stop, or I'm going to cum," I said, feeling increased sensations in my dick.

Madison got off me, turned and bent over to kiss me. "That was so awesome, Brent. I loved having you fuck me. Maybe next time I can make you go all the way!"

So she was already thinking about a next time. That got me aroused all over again.

I stood and joined Simone for a three-way kiss and sharing of tongues.

"I think it's time for all of us to cum," Simone said. "Maybe even at the same time."

"How?" I asked.

"How?" Madison asked at the same time.

Simone smiled. "I call it cuddle fucking. You guys are going to love this."

"Okay," I said, looking at Madison, who was stroking her dick.

Simone lay down on the couch/bed, facing the side. "Brent, come in behind me and fuck my pussy."

I obeyed, getting up behind her wonderful ass. I kind of wanted to fuck it again, but could tell how wet her pussy was, so I inserted myself. I slid right in.

"Mm ... oh!" Simone said.

I started fucking her, feeling new areas of her pussy as I came in at a different angle.

"Now ... Madison," Simone said, already getting a little out of breath. "Get behind Brent and fuck his ass."

"Oh!" I said, a little surprised, but also aroused by the thought of this beauty coming inside me. "I've ... um ... never ..."

"It'll be ... fun," Simone said. "Just lube him up."

I felt a cool sensation as Madison rubbed lube over my asshole. In a way, I was glad I was already fucking Simone. I was so turned on that the thought of something going up my ass was arousing.

Madison came up behind me. I felt the head of her rod push against my ass. I held still and tried to relax, my dick still deep inside Simone's pussy.

"Oh!" I said as Madison's head popped into my ass.

She pulled it out and pushed back in further. I felt a fullness as her thick meat went further up inside me. She pulled out and pushed back in. I felt her body touch mine as her dick got all the way inside.

I started moving my cock in and out of Simone. As I moved, Madison's dick slid in and out of my ass. I was fucking and being fucked at the same time!

"Shit, this feels good," I said.

Simone started moving quickly on my dick. "I ... oh ... thinking about you two ... I'm going to ... cum soon!"

"Me too!" Madison said. "Your ass feels amazing on my cock!"

Both Simone and Madison sped up, I relaxed and let these two women fuck me. Tingles started to form in my dick, and I knew I was close. This time I wasn't going to hold back.

"OH!" Simone cried out suddenly. "I'm ... cumming!"

Her hips started convulsing as she cried out, "ah ... ah ... AH!"

I felt Madison shove herself even deeper and hold it. "Oh ... fuck ... oh," she groaned.

As Madison started cumming, I could feel her dick swell and spurt out in my ass. I could feel it every time she pumped into me.

"Oh!" I cried as I felt a sharp pleasure erupt from deep in the base of my cock and travel up to the tip and out to the rest of my body. "Here I cum!"

I started spurting my own load into Simone -- rope after rope of cum filling her. It was an amazing feeling -- almost like I was cumming in my ass and dick at the same time. I'd never felt anything like that in my life.

It seemed like we came for hours, though it was really about a minute. I started moving slowly in Simone's pussy as she calmed. Madison did the same in my ass, eventually pulling out.

I laid on my back and Simone and Madison came up on either side. Simone stroked my dick as we three kissed and made out.

"What did we just do?" I said, a little in shock at what had just transpired.

"Whatever it was, it was wonderful!" Madison said.

"It sure was," Simone said.

"Best sex of my life," I said, holding both women by the shoulder and pulling them in for another kiss.

We showered together, taking time to wash all our parts -- even in our assholes! Simone knelt in front of us and sucked each of our cocks. As her and Simone made out, I took another turn on Madison and got her really hard.

"Can we do one more thing?" Simone asked.

"I'm game for anything now," I said.

"I want both of you to fuck me at the same time."

"Say what?" I asked.

"It feels so good," Simone said, dragging us out of the shower and starting to dry us off.

We went back to the living room. I watched as Madison licked Simone's pussy.

"Now lay on your back, Madison and fuck my ass."

Madison laid down, putting her legs over the edge, holding her erection while I lubed it and Simone's ass. Simone faced away from Madison and helped her enter.

"Oh ... your cock is so big!" she said.

The two fucked that way while I played with Simone's tits.

"Now ... um ... come between my legs and fuck my pussy," Simone said.

I moved up, touching Madison's legs as I positioned my cock. As I pushed in, I could feel Madison's dick moving in and out of her ass. It was a strange and wonderful feeling.

"Oh ... so good!" Simone moaned.

We started fucking in earnest. Each time we moved across each other's dicks I felt tingling. Simone came and screamed out in pleasure.

"AH ... AH ... AH!"

I came next, spurting a fresh round of jizz into her pussy.

"I'm going to cum too," Madison said.

"Cum in my mouth," I said without thinking.

I backed out, my dick popping from Simone's pussy, spurts of cum still shooting from me. Simone stood and came off of Madison's dick.

"Oh ... oh," Madison groaned.

I moved in and took her wonderful cock in my mouth. I felt her swell again and this time -- ropes of cum hit the back of my throat. I started swallowing the sweet tasting cum. I couldn't believe how much cum she had.

When she was done, she pulled out, cum still dribbling from her cock. She sat up and grabbed my cock, licking it clean. Madison and I then kissed, sharing each other's cum.

When we were done, we collapsed on the bed, spent but satisfied.

"Wow!" I said. "I've done things tonight I never dreamed I'd do."

"Are you glad?" Madison asked, stroking my chest.

"Oh yes," I said. "Very glad. You two are wonderful. I hope this isn't the last time we can share each other's bodies."

"Oh, it won't," Simone said.

"We think you're pretty wonderful too," Madison said.

We shared another three-way kiss, then fell asleep together.

We enjoyed lots more sex together. I even got to meet Kiley and fuck her ass while Madison sucked her dick. Marvelous!