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Two summers ago, my husband and I embarked on our usual road trip to hit up several indie music festivals. Invariably, we made our way to New York City, as we often did. We are in our late 30s and blissfully child-free, so we’re always aiming to find ways to mix in some adult pleasure. I pride myself on keeping fit with yoga, and my trim figure, green eyes and natural blonde hair help me get hit on by men — and women.

Over the years, Jake and I have enjoyed our fair share of threesomes with other girls, but that summer I’d really wanted to finally experience one with two men. Well, I got my wish, but with an unexpected twist.

We were at a club enjoying the sounds of some Romanian punk band, when I bumped into a redhead with curly hair as she passed through the crowd. She had creamy ivory skin and warm brown eyes behind her dark-rimmed hipster glasses.

“Sorry about that!” I tried to yell over the music.

The redhead smiled and leaned closer as she said, “What?”

“I said I’m sorry for smacking into you.”

She laughed and touched my arm, shouting, “That’s OK.”

Her touched was prolonged just enough to trigger a spark between us as our eyes locked again.

“What’s your name?” I yelled over the blaring guitar.

“I’m Sam.”

“Stephanie.” I gestured to myself as I spoke and then to the tall, dark handsome guy beside me as I said: “This is my husband, Jake.”

“Is this your first time here?” Sam asked.

“Nope, we come every year.” But before I could say more, someone shoved me into Sam’s arms.

“Whoa, there!” She deftly caught me as our breasts pressed together, and we were suddenly nose-to-nose.

“Well, it looks like we’re dancing now,”     I joked with an embarrassed laugh.

Sam caressed the side of my face and told me, “I think I’d like to do more than that.”

My husband nuzzled my neck and gave my butt a squeeze as he said, “Oh baby, this is getting good now.”

With my husband grinding against me from behind and Sam gyrating in front of me, the music’s beat felt hypnotic. I felt my pussy growing wetter and wetter. I wanted to tear off Sam’s clothes and have her right there.

She must have sensed my hunger because after the song ended, she tapped me on the shoulder and shouted in my ear: “I was on my way to the ladies room. Wanna come? It might be easier to talk there.”

Seeing our conspiratorial looks, Jake nodded at me — not even knowing exactly what he was encouraging me to do.

I nodded, too, but at Sam and headed off with her.

My husband and I generally have an “open bedroom door policy” when we’re on the road. But beyond finding chemistry with our playmates, it’s always about safe, sane and consensual fun.

I followed Sam through the crowd and out of the noise. In the middle of a set, the ladies room wasn’t too crowded, and the bright light made it much easier to check her out. Sam wore a bodycon black tank dress. She had a slim build with narrow hips, but still had a cute butt, which I noticed when she strutted into a stall. When she re-joined me at the sink, we were the only girls left inside.

“So,” Sam said washing her hands. “Are you and your husband into partying together?”

I checked my eye makeup in the mirror and grinned.

“Yeah, sometimes. What are you into?”

Sam reached over and played with the end of my long braid as she said, “Well, for starters, I really love blondes.”

“Well, my husband and I both love redheads. So aren’t we lucky?” I leaned in and planted a soft kiss on her lips.

Sam pulled me close, and we enjoyed a little tongue action before she eased back and confessed, “I’m not a natural redhead.”

I shrugged and replied, “I’m not a natural blonde.”

Sam laughed, but added, “That’s not all of it. Before we play, you need to know something about me.”

I braced myself for some horrible announcement, but instead Sam leaned in and whispered: “I have a dick.”

My eyes widened as I answered, “Really?”

“Is that OK?”

“You’re a…”

“I’m a man. I’m not trans. But I enjoy dressing up like a woman and going out.”

“Hey, we’re all artsy bohemians here. It’s cool with us.” I paused and added, “So, do you still like using your dick?”

“Of course I do. Would you be down with that?”

My eyes lit up. “I’ve been trying to get another man to join me and my husband, but this is even more fun! Jake is going to flip!”

We made our way out of the bathroom, and true to form, my husband was already there with my coat and purse.

“Second act isn’t that great. Do you two want to get out of here and have some fun?”

“Sure honey. Just one little thing.” I glanced back at Sam who nodded.

I leaned in and whispered Sam’s secret into Jake’s ear, and to my delight, he gave me a thumbs-up. Sam laughed heartily.

“It’s all good. Whatever you want, baby,” he told me.

Jake had had some bisexual flings in college, but these days he prefers women. Even though I expected his encouragement, it still really meant a lot to me that he’d let me explore my fantasy.

Once we got to the hotel, Jake wanted to start off watching Sam and I make out.

“I’m going to leave my top on, if you don’t mind,” Sam said. “I like my fake tits.”

“I like them, too.” I caressed the bulge in Sam’s panties. “And I like this.”

“You don’t mind?” Sam glanced at my husband.

“What she wants, she gets,” Jake said.

Sam was my first real transvestite partner, and I was determined to enjoy this unexpected chance.

“Can I suck you off?” I asked.

“Sure, honey.”

I peeled off the rest of my clothing, and we climbed on the bed. Sam left on the tank top dress and thigh-highs, but there was no concealing that gorgeous thick cock. I traced my tongue around the base of Sam’s shaft and worked my way up to its head. I was wild with lust.

Sam wrapped my braid around his hand and gently tugged my hair, while I sucked and swallowed his member. But my senses were overwhelmed by his decidedly feminine perfume.

The gender-blurring was really an unexpected turn-on. I’ve screwed women and men, but this was like a bonus mind-fuck. Once I had Sam’s dick super hard and almost to the point of no return, I motioned my husband over.

“I want you, too. Come here.”

“I have an idea,” Sam suggested. “Why don’t you suck on your man, and I’ll eat your pussy?”

“I love that idea!”

Jake grinned and told me, “I love you seeing you this frisky.”

I took a deep breath and swallowed my husband’s shaft, taking him all the way down my throat. He’s almost nine inches when he’s fully erect. Though I’d mastered my gag reflex long ago, Sam’s expert tongue knocked me for a loop. I gasped and gagged on Jake’s dick as Sam attacked my clit.

The muffled moans and groans filling our hotel room were a chorus of orgiastic delight. My body shuddered as Sam’s fingers probed my pussy while he continued to suckle my clit.

Meanwhile, my husband dutifully held me steady and kept my hair out of my face. His nicely toned abs were drawn taut, and his breathing had grown shallow, so I was sure he was close to climaxing.

I pulled back and released his shaft from my mouth, leaving a long thread of saliva dangling from my lips. 

“I want you to fuck me in the ass tonight,” I told my husband, looking up at him with cock-hungry eyes. “And I want Sam to pound my pussy at the same time.”

“You wanna be stuffed full of cock like the slut you are?” Jake asked with a grin.

“What’s this I hear about fucking?” Sam gave my butt a little slap and came up for air.

I nodded eagerly and told them: “I want you both to do me deep and dirty.”

“I think that can be arranged,” my husband said, reaching for the box of condoms on our nightstand and tossing a rubber to Sam.

I was so fucking wet with anticipation. I’d been fucked in both holes with toys, but never by two men at once — much less with one of the men looking like a woman.

Jake and Sam sandwiched me right between them, and with a little extra lube and maneuvering, I was packed completely full with dick.

At first, I had them be still, just so I could take in the sensation of being doubly penetrated. But Jake and Sam picked up their pace slowly and gradually, and once they got into a rhythm of thrusting, well, they blew my mind. When one pulled out, the other pushed in. They worked in tandem to make me crazy. I already love a good fuck as it is, but that experience was electric, feeling my body so tight and stuffed. It was sheer bliss.

Meanwhile, my husband played with one of my nipples and kissed my neck, sending chills up and down my spine. And every now and then, Sam would surprise me with a sexy kiss on the mouth. Every inch of me felt alive and ravished by pure pleasure. In what seemed like no time at all, I had one of the most intense orgasms of my life as both my ass and pussy clenched around the two hard dicks drilling me. After I came — and both Jake and Sam shot off inside me — I lay limp like a rag doll.

Sam caught me and kissed my forehead, saying: “That was exquisite.”

My husband caressed my back and added, “Yes, it was. I can’t believe we waited so long to try this.”

All I could do was close my eyes and sigh with pleasure. Eventually, we all made it to the en suite hot tub to relax and soak. But after that, Sam touched up his makeup and disappeared into the night.

" />

Two Summers Ago

  • 1

Storyline

Two summers ago, my husband and I embarked on our usual road trip to hit up several indie music festivals. Invariably, we made our way to New York City, as we often did. We are in our late 30s and blissfully child-free, so we’re always aiming to find ways to mix in some adult pleasure. I pride myself on keeping fit with yoga, and my trim figure, green eyes and natural blonde hair help me get hit on by men — and women.

Over the years, Jake and I have enjoyed our fair share of threesomes with other girls, but that summer I’d really wanted to finally experience one with two men. Well, I got my wish, but with an unexpected twist.

We were at a club enjoying the sounds of some Romanian punk band, when I bumped into a redhead with curly hair as she passed through the crowd. She had creamy ivory skin and warm brown eyes behind her dark-rimmed hipster glasses.

“Sorry about that!” I tried to yell over the music.

The redhead smiled and leaned closer as she said, “What?”

“I said I’m sorry for smacking into you.”

She laughed and touched my arm, shouting, “That’s OK.”

Her touched was prolonged just enough to trigger a spark between us as our eyes locked again.

“What’s your name?” I yelled over the blaring guitar.

“I’m Sam.”

“Stephanie.” I gestured to myself as I spoke and then to the tall, dark handsome guy beside me as I said: “This is my husband, Jake.”

“Is this your first time here?” Sam asked.

“Nope, we come every year.” But before I could say more, someone shoved me into Sam’s arms.

“Whoa, there!” She deftly caught me as our breasts pressed together, and we were suddenly nose-to-nose.

“Well, it looks like we’re dancing now,”     I joked with an embarrassed laugh.

Sam caressed the side of my face and told me, “I think I’d like to do more than that.”

My husband nuzzled my neck and gave my butt a squeeze as he said, “Oh baby, this is getting good now.”

With my husband grinding against me from behind and Sam gyrating in front of me, the music’s beat felt hypnotic. I felt my pussy growing wetter and wetter. I wanted to tear off Sam’s clothes and have her right there.

She must have sensed my hunger because after the song ended, she tapped me on the shoulder and shouted in my ear: “I was on my way to the ladies room. Wanna come? It might be easier to talk there.”

Seeing our conspiratorial looks, Jake nodded at me — not even knowing exactly what he was encouraging me to do.

I nodded, too, but at Sam and headed off with her.

My husband and I generally have an “open bedroom door policy” when we’re on the road. But beyond finding chemistry with our playmates, it’s always about safe, sane and consensual fun.

I followed Sam through the crowd and out of the noise. In the middle of a set, the ladies room wasn’t too crowded, and the bright light made it much easier to check her out. Sam wore a bodycon black tank dress. She had a slim build with narrow hips, but still had a cute butt, which I noticed when she strutted into a stall. When she re-joined me at the sink, we were the only girls left inside.

“So,” Sam said washing her hands. “Are you and your husband into partying together?”

I checked my eye makeup in the mirror and grinned.

“Yeah, sometimes. What are you into?”

Sam reached over and played with the end of my long braid as she said, “Well, for starters, I really love blondes.”

“Well, my husband and I both love redheads. So aren’t we lucky?” I leaned in and planted a soft kiss on her lips.

Sam pulled me close, and we enjoyed a little tongue action before she eased back and confessed, “I’m not a natural redhead.”

I shrugged and replied, “I’m not a natural blonde.”

Sam laughed, but added, “That’s not all of it. Before we play, you need to know something about me.”

I braced myself for some horrible announcement, but instead Sam leaned in and whispered: “I have a dick.”

My eyes widened as I answered, “Really?”

“Is that OK?”

“You’re a…”

“I’m a man. I’m not trans. But I enjoy dressing up like a woman and going out.”

“Hey, we’re all artsy bohemians here. It’s cool with us.” I paused and added, “So, do you still like using your dick?”

“Of course I do. Would you be down with that?”

My eyes lit up. “I’ve been trying to get another man to join me and my husband, but this is even more fun! Jake is going to flip!”

We made our way out of the bathroom, and true to form, my husband was already there with my coat and purse.

“Second act isn’t that great. Do you two want to get out of here and have some fun?”

“Sure honey. Just one little thing.” I glanced back at Sam who nodded.

I leaned in and whispered Sam’s secret into Jake’s ear, and to my delight, he gave me a thumbs-up. Sam laughed heartily.

“It’s all good. Whatever you want, baby,” he told me.

Jake had had some bisexual flings in college, but these days he prefers women. Even though I expected his encouragement, it still really meant a lot to me that he’d let me explore my fantasy.

Once we got to the hotel, Jake wanted to start off watching Sam and I make out.

“I’m going to leave my top on, if you don’t mind,” Sam said. “I like my fake tits.”

“I like them, too.” I caressed the bulge in Sam’s panties. “And I like this.”

“You don’t mind?” Sam glanced at my husband.

“What she wants, she gets,” Jake said.

Sam was my first real transvestite partner, and I was determined to enjoy this unexpected chance.

“Can I suck you off?” I asked.

“Sure, honey.”

I peeled off the rest of my clothing, and we climbed on the bed. Sam left on the tank top dress and thigh-highs, but there was no concealing that gorgeous thick cock. I traced my tongue around the base of Sam’s shaft and worked my way up to its head. I was wild with lust.

Sam wrapped my braid around his hand and gently tugged my hair, while I sucked and swallowed his member. But my senses were overwhelmed by his decidedly feminine perfume.

The gender-blurring was really an unexpected turn-on. I’ve screwed women and men, but this was like a bonus mind-fuck. Once I had Sam’s dick super hard and almost to the point of no return, I motioned my husband over.

“I want you, too. Come here.”

“I have an idea,” Sam suggested. “Why don’t you suck on your man, and I’ll eat your pussy?”

“I love that idea!”

Jake grinned and told me, “I love you seeing you this frisky.”

I took a deep breath and swallowed my husband’s shaft, taking him all the way down my throat. He’s almost nine inches when he’s fully erect. Though I’d mastered my gag reflex long ago, Sam’s expert tongue knocked me for a loop. I gasped and gagged on Jake’s dick as Sam attacked my clit.

The muffled moans and groans filling our hotel room were a chorus of orgiastic delight. My body shuddered as Sam’s fingers probed my pussy while he continued to suckle my clit.

Meanwhile, my husband dutifully held me steady and kept my hair out of my face. His nicely toned abs were drawn taut, and his breathing had grown shallow, so I was sure he was close to climaxing.

I pulled back and released his shaft from my mouth, leaving a long thread of saliva dangling from my lips. 

“I want you to fuck me in the ass tonight,” I told my husband, looking up at him with cock-hungry eyes. “And I want Sam to pound my pussy at the same time.”

“You wanna be stuffed full of cock like the slut you are?” Jake asked with a grin.

“What’s this I hear about fucking?” Sam gave my butt a little slap and came up for air.

I nodded eagerly and told them: “I want you both to do me deep and dirty.”

“I think that can be arranged,” my husband said, reaching for the box of condoms on our nightstand and tossing a rubber to Sam.

I was so fucking wet with anticipation. I’d been fucked in both holes with toys, but never by two men at once — much less with one of the men looking like a woman.

Jake and Sam sandwiched me right between them, and with a little extra lube and maneuvering, I was packed completely full with dick.

At first, I had them be still, just so I could take in the sensation of being doubly penetrated. But Jake and Sam picked up their pace slowly and gradually, and once they got into a rhythm of thrusting, well, they blew my mind. When one pulled out, the other pushed in. They worked in tandem to make me crazy. I already love a good fuck as it is, but that experience was electric, feeling my body so tight and stuffed. It was sheer bliss.

Meanwhile, my husband played with one of my nipples and kissed my neck, sending chills up and down my spine. And every now and then, Sam would surprise me with a sexy kiss on the mouth. Every inch of me felt alive and ravished by pure pleasure. In what seemed like no time at all, I had one of the most intense orgasms of my life as both my ass and pussy clenched around the two hard dicks drilling me. After I came — and both Jake and Sam shot off inside me — I lay limp like a rag doll.

Sam caught me and kissed my forehead, saying: “That was exquisite.”

My husband caressed my back and added, “Yes, it was. I can’t believe we waited so long to try this.”

All I could do was close my eyes and sigh with pleasure. Eventually, we all made it to the en suite hot tub to relax and soak. But after that, Sam touched up his makeup and disappeared into the night.

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