Our first trip away

It was a cold January night, but the snow and freezing temperatures couldn't stop Rick and I from having a steamy weekend getaway. We had been dating for a year, keeping our relationship a secret as we navigated our lives as closeted gay men. I, Steve, was a recent college graduate, slim and feminine with a passion for cross-dressing, and Rick, my dominant and experienced partner, was a local college professor, tall and broad with a grey beard.

For this special weekend, Rick had planned a trip to a beach town in New Hampshire, just the two of us in a cozy hotel room. I packed my bags with excitement, including some of my favorite outfits: a short, tight grey sweater dress, a cheerleading uniform with white tights and sneakers, and a schoolgirl outfit with black tights and knee-high socks. I knew Rick loved my cross-dressing and I couldn't wait to put on a show for him.

As we arrived at the hotel, the snow was falling gently outside, creating a romantic and secluded atmosphere. We unpacked our things, and I immediately felt the anticipation building. I wanted to surprise Rick, so I suggested we go to a local gay bar that night. He loved the idea, and we got ready together, drinking wine and flirting shamelessly.

I slipped into my grey sweater dress, the fabric hugging my slim frame, and black crotchless nylons that accentuated my legs. I put on a pair of black heels and a brown shoulder-length wig, completing the transformation. Rick's eyes lit up when he saw me, and he pulled me close, whispering naughty promises in my ear.

We headed out into the snowy night, hand in hand, and made our way to the bar. Inside, the warmth and energy enveloped us, and we spent a few hours dancing and flirting, feeling free and desired. As midnight struck, we decided it was time to retire to our private haven.

Back in our hotel room, the passion ignited. Rick pulled me close, his strong arms around my waist, and kissed me deeply. I could taste the wine and the desire on his lips. He slowly undressed me, taking his time to savor every inch of my body. My dress fell to the floor, followed by my wig, and I stood before him in just my nylons and heels.

"You look so fucking sexy, Steve," Rick growled, his eyes dark with desire. "I want you now."

He pushed me gently onto the bed and climbed on top of me, his weight pressing me into the soft mattress. I moaned as I felt his hard cock against my thigh, already leaking pre-cum. Rick positioned his throbbing cock against my smooth hole.

With one smooth thrust, he entered me, filling me up completely. I gasped as the pleasure washed over me, my body welcoming his invasive cock. I look up at Rick and moan as he began to move, his hips thrusting slowly at first, then with increasing speed and intensity. I wrapped my legs around his waist, meeting his thrusts with my own desperate need.

"Oh fuck, Steve, your tight pussy feels so good around my cock," Rick panted, his voice hoarse with lust. "I've been thinking about fucking you all night."

His words sent shivers down my spine, and I begged for more. "Please, Rick, fuck me harder. I want to cum with your cock inside me."

Rick obliged, grabbing my hips and pounding into me with forceful thrusts. The bed creaked beneath us as our bodies moved in perfect rhythm. I cried out in pleasure, my voice echoing in the room, uncaring if anyone heard us. I was lost in the sensation, my cock rock hard and leaking onto my stomach. The sensation is intense I begin to shoot a huge load onto my smooth body as Rick continued fucking me.

As I felt my orgasm building, I tightened my legs around Rick's waist, pulling him deeper inside me. With a few more powerful thrusts, we both tumbled over the edge together, crying out in ecstasy. Rick's cock pulsated inside me and began fucking me very hard and fast until Rick started grunting and I felt the warm sensation of his cum shooting inside of me. We lay entangled for a moment, catching our breath, before he gently pulled out.

We curled up together, our bodies still glistening with sweat, and chatted for a while, our arms wrapped around each other. But soon, the familiar tingle of desire started to build again. I couldn't get enough of Rick, and the feeling was mutual.

I slipped out of bed and walked over to my bag at Rick’s direction retrieving the cheerleading uniform I had packed. I put on the short pleated skirt and white tube top, white tights, and sneakers. My hair fell loosely around my shoulders, and I applied a fresh coat of red llipstick, turning to face Rick with a mischievous grin.

His eyes widened at the sight of me, and his cock twitched in response. "You naughty boy, Steve," he said, his voice full of approval. "Come here and let me show you how much I appreciate this outfit."

I walked over to the bed, my heart pounding with excitement. Rick pulled me onto his lap and kissed me deeply, his tongue exploring my mouth. He reached down and grabbed my hard cock, stroking it gently. I moaned into his mouth, my body trembling with anticipation.

"Suck my cock, baby," Rick whispered, his breath hot against my ear. "Show me how much you love it."

I didn't need to be told twice. I got down on my knees and took his thick, cut cock in my hand, stroking it slowly. I teased the tip with my tongue, tasting the salty pre-cum, before taking him into my mouth. I bobbed my head up and down, taking as much of him as I could, my makeup smearing slightly as I focused on giving him pleasure while I look up at Rick.
Rick moaned above me, his hands tangling in my hair. "That's it, baby, take my cock. You're such a good little cock sucker."

His words of encouragement spurred me on, and I hollowed my cheeks, sucking him deeper. I cupped his heavy balls with one hand, massaging them gently as I continued to suck and lick his shaft. I could feel his cock twitching in my mouth, and I knew he was close. With a few more skillful strokes, he exploded, his warm cum hitting the back of my throat. I swallowed eagerly, milking him dry and relishing the taste of him on my tongue.

We took a short break, our bodies satiated temporarily, and turned on some porn to keep the mood going. As we watched a steamy scene of teacher-student roleplay, our desire ignited once more. This time, I put on my schoolgirl outfit—a short plaid skirt, a white button-down shirt, black tights, and knee-high socks. My hair was tied into pigtails, and I carried a fake schoolbook to complete the illusion.

Rick played along, assuming the role of the teacher. "Now, now, Miss Steve," he said, feigning a stern tone. "You know the rules about staying after class. I'm going to have to teach you a lesson."

I giggled nervously as he pulled me over his lap, my skirt riding up to expose my bare ass. Rick raised his hand and landed a sharp smack on my cheeks, leaving a stinging sensation that only fueled my arousal.

"Oh, Professor Rick," I cooed, playing my part. "I promise I'll be a good student. Please, teach me everything you know."

Rick chuckled and delivered another smack, this time lower, closer to my tight hole. I squirmed, feeling the heat building between my legs. "Please, Professor, I need to be taught a proper lesson. Use your cock to educate me."

Rick's cock was already hard and ready, so he didn't need to be asked twice. He lined up his cock with my hungry hole and pushed inside, filling me with his thickness. I moaned, feeling stretched and deliciously full. Rick began to thrust, his hips slapping against my ass cheeks, creating a rhythmic sound that filled the room.

"That's it, take it all, Miss Steve," he grunted. "You're such a naughty student, always craving the teacher's cock."

I cried out in pleasure, encouraging him to go harder and deeper. The sound of our flesh slapping together filled the room, accompanied by our moans and desperate pleas. Rick reached around and stroked my hard cock in time with his thrusts, sending shocks of pleasure through my body.

"Oh fuck, Professor, I'm gonna cum!" I shouted, unable to contain my orgasm any longer and I shoot another huge load while Rick’s cock is inside of me.

With a few more powerful thrusts, Rick once again cums inside me. We make out after he cums, my nyloned legs wrapped around him we both tumbled over the edge. Rick's cock pulsed inside me. We collapsed onto the bed, our bodies sticky and satiated. We had cum three times together, each time more intense than the last, and still, the night was young.

As we lay curled up together, the sun began to rise, casting a soft light into the room. We dozed off for a few hours, our bodies intertwined, only to wake up later that afternoon with renewed lust. Our weekend of forbidden love continued, and we explored every inch of each other until it was finally time to check out.

This trip had been a testament to our passion and desire, and as we drove back home, I knew our love would remain a secret worth keeping.