holiday-femboy-romance
FIRST TIME SEX STORIES

Holiday Femboy Romance

Holiday Femboy Romance

by josiejamesxoxo
20 min read
4.41 (13800 views)
adultfiction

INTRODUCTION

I want to start off this story by telling the reader a bit about me. I'm 32, British, around 6 feet tall, toned build, short brown hair, clean shaven and I'm married, to a woman and have been for 7 years.

My wife and I have just returned from a holiday to Tenerife, it's a Spanish island off the coast of Africa, with beautiful beaches and hotel resorts.

I love my wife, but recently, we haven't been having sex for a good 6 months. I don't blame either of us, it's just work, tiredness and the small matter of the fact I can't stop dreaming about cock. I've always been a bit "bi" which sounds stupid but yeah, I have never been romantically attracted to men, only women. But sexually, yeah I love the thought of cock, and the reality of it too. I'm a regular user of Grindr but to this day, have never ever met up with anyone. I get freaked out and get scared that they'll out me to my wife. But this hasn't stopped me from investing in all sorts of dildos, vibrators, butt plugs that are all safely hidden in the attic of our home.

THE HOLIDAY

I knew that in Tenerife, there was a great gay scene, i'd seen as much from when I used Grindr to search around the area of Los Cristianos, the area we were staying. I saw loads of profiles located there, bottoms, tops, twinks, bears even trans. You name it, it was available in Los Cristianos. Like a big gay pick 'n' mix!

So this was it, I had made the decision that whatever happens, I would at least suck some cock at one point across the 10 nights we were staying there. I just had to! You may be wondering how I could go about this, as I was travelling, staying and sleeping with my wife. Well this is where her migraines come in, she gets them frequently, i'd say every two-three days at homes. They aren't serious but she tends to just want to sleep in a blacked-out room for a few hours. When we're on holiday, it can be more frequent because of the sunshine. To push myself even further, I packed a 50ml bottle of water based lube, a pack of Ribbed condoms and my favourite Black lace jock-strap.

ARRIVAL IN TENERIFE

After the flight was a little delayed, and a four and a half hour flight (Which included a lot of me checking the sexy twinks and other smooth looking femboys at the airport and on the plane itself) we arrived at the hotel. It's a small hotel, around 25 rooms all over looking an average sized swimming pool. As we were being shown around the receptionist pointed out some steps adjacent to the pool,

"Down here are showers, bathrooms and changing facilities, they are open all day and you're free to use them for the pool."

I immediately got excited. Not to sound like a pervert but I was instantly imagining peeking through a crack of a cubicle door and spying a hard bodied sun-cream lathered guy with soft skin, hard muscles and bulging speedos. I looked down and could feel myself getting hard, I must have been seriously day dreaming because the next thing I knew we were in the room and I heard the receptionist softly say,

"Gracias, enjoy your holiday".

I thought to myself, well if it's anything to do with what I was thinking of, I certainly will.

DAY TWO

After arriving at the hotel the night before and unpacking everything - I was careful to ensure that I waited to remove my 'special items' away from my wife's eyes and hide them under my side of the bed - We decided to laze around the pool and relax. Luckily the hotel wasn't the type of hotel where you have to 'reserve' sunbeds by waking up at 5am and sprinting outside with two towels. So after breakfast, we walked over to the pool and my wife asked where i'd like to go, I'm not much of a sun bather so I suggested somewhere with some shade, then I spotted two sunbeds near the stairs down to the changing rooms and toilets. I thought this would be ideal as I could maybe see if there are any frequent visits by anyone, and by anyone, I know exactly the type i'm looking for.

After a few hours. There wasn't really anybody peaking my interest, then, at around 12pm, I saw him. He looked in his early twenties, short, curly brown hair, olive skinned, cute face, clean shaven, muscular but no serious definition and legs shaved smooth. He definitely looked like he was from the Mediterranean, he wore a short sleeved linen shirt that was unbuttoned, with a pair of red speedos and black haivanas. Instantly my cock began twitching in my swimming shorts, I glanced to my right to make sure my wife hadn't clocked me, clocking him. She hadn't, she was fast asleep basking in the sun. I continued looking him up and down, I hate to stereotype people but he certainly had the gait of someone who enjoyed same sex relationships shall I say. He was confident, almost bouncing as he walked, but I was completely drawn to the bulge in those tight red speedos. Every step he took, the bulge pulsed slightly, I saw the outline of his flaccid penis, surrounded by his round balls.

He looked around and we caught eyes, one side of his mouth lifting towards his cheek, the smile was almost naughty. I smiled back, but trying to play it straight I did the head nod to pair with it. He continued strutting until he paused and laid down the bag he was carrying over his shoulder on to a sun bed. That's when I saw it, he turned 90 degrees and his beautiful pert bubble butt, like a homing beacon for my semi erect cock was there, staring at me from across the idyllic blue swimming pool. In that moment I wanted to dive right into the pool, swim across and dive right into him.

"Do you want a drink?" my wife uttered, like an almost literal pin bursting my homo-erotic bubble.

"Erm, yeah, sure, I'll get them. Water?" I mumbled, trying to remember where I was and who I was with.

"Yeah thanks" she replied.

I looked back across the pool and he was already gone. His towel was down but he was nowhere to be seen. I thought maybe he had gone to the changing rooms, I deliberated going down there to investigate but thought better of it. I was convinced that the time would literally come, but first I needed to get some drinks. I got up, slipped on my flip-flops and made my way to the bar, I rubbed my eyes to adjust to the shaded bar and as I unfurled my hand from across my eyes I saw it, that beautiful tight ass smothered in those crimson polyester swimming trunks. I followed the lower back up to his shoulders slowly, taking him all in and then I realised...he was looking right at me with his chin almost resting on his shoulder. I tried to play it cool with another smile and nod but he knew. He winked at me, and at the same time smiled and turned back to the bar, he collected his Fanta limon and walked towards me, he looked me up and down and as he was brushing by, raised his eyebrows with a smile.

I froze, my heart was beating out my chest. Was I flirting? With a man, whilst my wife is literally 20 metres away? Maybe I was being silly, but my heart couldn't slow down. 'God I need a drink' I thought.

After a few more hours of basically playing stare tennis with him, and watching him slather what looked like baby oil all over himself every 30 minutes. I decided to head down to the changing rooms, I needed a piss but to be honest, I wasn't sure I would just be having a wee because I was so horny I knew my cock needed some serious attention. I looked across to my wife who was involved in some serious book reading and I took my leave,

"Just going to the toilet" I muttered. She nodded.

I got to the top of the steps, with a stone archway across the entrance and some soft yellow lights directing the way and I took a deep breath. As I got the bottom I was slightly shocked by how small it was. In Front of me there was a pane of frosted glass and behind it, two urinals. Then to the right a cubicle with a 'MALE' figure on it, following the room round was four sinks and mirrors, then two cubicles with 'FEMALE' figures on them and finally, two shower cubicles. I tried the male cubicle but the door was locked. I really did need to pee so I ushered round to the urinal and took out my cock, as soon as I grabbed it I knew I had to release the tension. It's worth pointing out that my cock is a grower, not a shower, when flaccid it's around 3-4 inches but when erect, it more than doubles. As I removed it from my shorts, it was around 5 inches long and had definitely thickened. I began to pee and as I did I heard the cubicle toilet flushing and an older gentleman exit, he used the sink and made his way up the stairs.

"Oh sorry lad" I heard someone say at the top of the stairs, the voice sounded old and northern English, it must have been the man.

I thought nothing of it until I saw some black haivanas making their way down the stairs, attached to him...I was like a deer in the headlights, I had almost finished peeing but I could feel myself getting hard again. Whilst staring forwards, almost lasering the white tiles ahead of me, I smelt the faint scent of coconut oil along with jean paul gaultier cologne.

"Hey there..." he said, "...I'm Leo",

I couldn't believe it I thought, he was stood literally next to me, removing his cock from the speedos and he was about to pee. I realised I hadn't replied so I jumbled out,

"Oh Hi i'm Dan".

I looked forwards again, doing everything I could to resist looking down at his cock. Wrestling with the confusion of why he chose to piss next to me rather than use the empty cubicle. He had an accent, definitely spanish.

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"You are here on holiday yes?" he said, smiling.

"Erm yes, are you?" I replied as I did my best to tuck my semi erect cock into my shorts.

"I am living here actually." He said, smiling again.

"Oh, in the hotel?" I questioned, making my way to the sinks.

"Yes, the owner is my friend. I work in bars around here." he stated as he sauntered over next to me again.

He put his hand on the sink and turned to face me as I took some paper towels.

"Who is that with you by the pool? Is it your wife?" my wedding ring was literally in his face, he knew the answer before he even asked the question.

"Yeah" I said.

At this point my imagination was torturing me, I wanted to grab him and start kissing every inch of his oiled skin there and then. He took a few seconds, then he bit his lip and looked down towards my crotch,

"That is a shame, no?" he said as his eyes moved upwards along my chest and up to meet my own.

My heart began beating again, I thought a million and one things until I thought to myself, fuck it. I looked down at that bulge in his speedos and said,

"Yeah" I met his gaze again "It is".

He smiled, the biggest smile I had seen from him yet and he began to laugh quietly. He brushed past me and before he began up the stairs, he turned and said,

"Maybe we will speak again Dan, maybe here, or maybe in room 21?".

I didn't know what to say, he could tell. He laughed again and made his way up the stairs. As his shadow evaporated I exhaled, was this it. Am I finally going to live out my fantasy? I couldn't believe it. My cock at this point was almost escaping from the waistband of my swimming shorts I was so hard. Then I suddenly realised, I'd told my wife I was going for a wee and that was about 5 minutes ago. I spashed some cold water on my face, waited 20 seconds for my cock to relax and made my way back to reality.

After meeting Leo in the toilets I didn't speak to him again. We looked over at eachother a few times but my wife and I went out to lunch and when we returned Leo's sunbed was empty.

DAY THREE

We had made plans to go the zoo and we both had a good time. However I couldn't shake the thought of Leo bouncing on my cock all day and to be honest, I equally thought about me riding him. I'd obviously pleasured myself anally plenty back at home. However, I'd say 90% of my fantasies involved me topping. However I always thought about switching and how hot it would be, just taking it in turns, ravishing eachothers boy pussies.

When we returned to the hotel from the zoo, I looked around the pool for Leo but again, he was nowhere to be found.

DAY FOUR

Jackpot! I woke up early, took a book out onto the balcony with one eye reading and the other keeping an eagle eye on activity by the pool. After an hour of reading I made my back inside to find my wife cradling her head between her knees on the bed.

"Migraine?" I suggested, doing everything in my power to mask my excitement.

"Yep, fucking bad too, this could be an all-dayer".

I grabbed a bottle of water and some medication from the first aid kit we'd brought,

"Take these and i'll grab you some fruit from the breakfast bar okay?" I said.

"Thank you, i'm sorry, are you okay to just have a pool day on your own?" she replied.

"Don't worry about me, I'll be fine. You just rest and make sure you're okay for tomorrow alright?" I said, putting on my best Florence Nightingale act.

She thanked me and I threw on a top and went to the breakfast bar. I grabbed some fruit and some juice and began making my way back, I peered across to the pool and saw Leo, laying a towel down on to a sunbed. Today he was wearing an almost sheer black robe paired with a black pair of speedos with a thick ribbed waistband. I took the long route back to the hotel room ensuring i'd walk past Leo.

As I approached his sunbed, I knew I had to start being more confident around him,

"Morning you" I said, boldly.

"Good morning Mr Dan, how are you today?" He said, lifting his sunglasses away from his face.

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"I'm great thanks Leo, will you be by the pool today then?" I said, trying not to stare at the glorious outline of his latin cock and balls.

"Of course, will I see you?" He said smiling.

"You will" I replied, smiling back.

"And your wife?" He said, more concerned.

"No, just me today, she's not well" I said, realising I was basically holding the contents of a fruit basket in my hands.

"Oh that is sad, but not sad for me" He said, licking his lips and looking up at me, almost inviting me to think of him sucking my cock and staring up at me.

I let the urge take over me and ran my gaze along his soft but chiseled jaw line, down his chest and stomach and racing down to his bulge.

"Me neither" I said, I returned back to his eyes and winked at him. "Adios for now" I said, proud of myself and headed back to the room.

As I entered the room, it was almost in complete darkness and I heard my wife breathing slowly and peacefully, she was asleep. I knew this was my chance. I placed the fruit onto her side table, kissed her on the forehead to check she was asleep. Once confirmed, crept round to my side of the bed and got onto my knees - Hopefully not for the last time today - I got hold of my mini satchel containing my jock strap, condoms and lube and made my way to the toilet. I locked the door quietly and slowly removed my shorts. I took out the jockstrap and slid one ankle in and then the other and slowly let the lace brush up my legs.

"God I love that feeling" I said to myself.

I got the my upper thighs and took one hand to cup my cock and balls and used the other to pull the jockstrap into place, ensuring maximum bulge. The front of the jockstrap is almost a satin material, with the sides and back being black lace that grips so perfectly the skin. I grabbed the strings that sit underneath my ass cheeks and ensured they were in position, giving my butt the perfect lift and I slipped my shorts back on. I took two condoms packets and the bottle of lube and placed it into my shorts. I emerged out of the bathroom, feeling incredible and exited the room almost silently.

I made my way to the pool and found a sunbed directly opposite Leo, meaning we can make perfect eye contact all day. As I laid down on to the sunbed, we caught eyes again and Leo smiled and I smiled back. He turned to look at the changing room stairs archway and I followed suit. I turned back at him and he pointed to his wrist, he then held up both hands with all ten fingers pointing in the air and then pointed back at his wrist and followed with a wink. I couldn't stop myself from smiling like an excited teenager who's just had their first kiss. I nodded and Leo settled back on to his sunbed, as did I.

Ten minutes I said to myself. Ten minutes until my fantasy becomes a reality. I started imagining Leo again, both of us rubbing our bodies together, almost sliding off of eachother as our suntan oil soaked skin is frictionless but his speedos and the satin of my jock strap brush together, almost yearning to become a part of eachother. I realised my thoughts, yet again had sent signals to my cock and I was becoming hard again, I looked up and Leo was gone, had ten minutes passed by so quickly? Then out the corner of my eye I saw him, just in his black thick waistline speedos pulsating past me, he almost whispered,

"See you in 30 seconds Danny..." He continued and I have to say, that felt like it was the longest 30 seconds i've had in my life.

"27, 28, 29...30, here we fucking go" I screamed internally.

I adjusted myself and made my way to the steps, as I got there I was met with a sign, 'FUERO DE SERVICIO - OUT OF ORDER'

"What?!" I said out loud.

And then I heard a soft whisper,

"Danny, is that you?" It was Leo, coming from the bottom of the stairs.

"Yes, what's going on?" I whispered back.

"The sign, it is me, don't worry. Nobody will come." I smiled, hearing this from Leo.

It was almost calming, the fear of getting caught almost dissipated in that moment and I stepped around the sign and made my down to my fantasy.

TOUCHDOWN

As I touched down on to the tiled floor, Leo met me, inches away, I could smell him again, but I wanted to taste him.

"Are you okay Danny?" he whispered. I smiled, shy again,

"I've never done..." Leo pressed his hand on to my mouth.

"Silencio Danny, you will love all of me okay?" I nodded, his hand still pressed against my lips.

Then he slowly returned his little finger and his ring finger to his palm and placed his thumb under my chin, Leo began pushing his middle and index finger into my lips, I obliged and softly opened my mouth. I had done this to my own fingers countless times but this felt so much better, I completely relaxed my mouth and met his fingers with my wet tongue. I took my hands and placed them on to Leo's waist, he felt so strong but so smooth and soft, I began moving my hands across his tight body and he placed his other hand on my chest as I continued to play with his fingers inside my wet mouth. Danny leant in towards me and whispered in my ear,

"You suck good Danny, you want to taste more of me?" I nodded and smiled.

He took my hand and guided it towards his bulging cock, I cupped all of him and instantly was drawn closer to him, he removed his fingers from my mouth as I continued to fondle his ever sweelling speedos. Leo placed his hand and his other on to the waistband of my shorts and began pull them down, I let out a moan and Leo smiled. I could feel his knuckles brushing my satin wrapped cock and Leo let out a quiet giggle

"Muy travieso Danny" he whispered.

My shorts were now by my ankles so I stepped out of them and towards Leo. I looked him in the eyes, down at his lips and took hold of his face. Suddenly I was filled with confidence and life, like i'd done this a thousand times before. I had, only it was always in my head, but now I got to play it out for real.

With my new found confidence, as Leo admired my heavy bulge and bubble butt, I did the same. My hands still around his face and I began to guide him backwards, until his back met the cold tiles on the wall. I brushed my nose with his and pushed my lips close, they met Leo's pouted pillowed lips and our mouths began to open in tandem. Our tongues gesturing to eachother and dancing inside our mouths. I pushed my body close to Leo as his slim but strong arms wrapped around my body, his hands almost massaging my lower back, Leo began to feel my ass cheeks, squeezing them and pulling them apart and then together as we continued to make out. Our cocks began pushing against eachother, almost dry humping. Leo came away for air and said

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