My Trip to Gibraltar- My First Time With an Escort - Cover

My Trip to Gibraltar- My First Time With an Escort

by Zak

Copyright© 2026 by Zak

Fantasy Sex Story: my hobby takes me to the next level

Caution: This Fantasy Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Fiction   Masturbation   Oral Sex   Safe Sex   Big Breasts   Prostitution   .

I headed down to the restaurant after taking a shower, and I took a table on the balcony looking out over the sea. My first couple of days in Gibraltar had been very enjoyable, and I was eager to do some sightseeing, then I had some fun and games to look forward to the following day.

I ordered a cold beer and a club sandwich with fries. As I waited for my food, I thought about my morning and how much fun it had been. After eating and a couple more beers, I went and had a wander around the town. I had just walked into the town square when my phone pinged. It was my burner. It was Sarah, the escort I had arranged to meet the following day, who apologised and asked if we could put our meeting back an hour. I responded and said it was okay with me. She sent me the street address and told me she would see me at five o’clock.

I had a few drinks in the town before heading back to the hotel. I had a couple of G&Ts on the balcony. Then I was off to bed. My head is full of thoughts about Sarah and what fun might be on offer.

I had been single since the death of my wife in a car accident, which had been five years ago. I had not craved female company as such; I didn’t want another wife. I was happy on my own, doing my own thing, plus work took me away for weeks at a time. I had a good job; it paid well, so I had a healthy bank balance. But I craved female touch, female attention. I used to be addicted to eating pussy, and I guess I still am.

I woke up early and was in the shower when I felt nerves kicking in. I had not seen an escort before, well, not for a full escort-style meeting. I had had massages and hand jobs, but this was not a step up. It had been a while since I had eaten a pussy, and I really wanted to do that with Sarah.

I got dried off and dressed before heading down for breakfast. I had the full English and a pot of tea. After breakfast, I went out to do some sightseeing. I took a walk into town and signed up for one of the guided tours. It was great fun, seeing the famous caves and getting my picture taken with one of the infamous Barbary macaques. I even go to see the Tunnels of the Great Siege, the World War II Tunnels, and the Moorish Castle.

It was nearly three o’clock by the time I was dropped off back in the town. I jumped on a bus to take me to the hotel. I had a coffee in my room, then shaved and had a long shower. Then I got changed, and I locked my phone in the room safe with my wallet and ID. I took twice as much cash as she had told me her fee was.

It was four o’clock as I walked out of the hotel. I used the maps app on my burner phone to find her street. It was closer than I thought, so I had time to kill. The street was full of shops, bars and restaurants. I took a seat in a bar where I could see her door. The waiter took my order, and I had an orange juice.

The nerves were kicking in again. I was worried that she might have a guy in there before me, and I was a bit worried about eating her pussy if she had another guy in there just before I arrived.

I decided if another guy came out, I would just take the massage and hand job and leave. Then a young, shapely blonde girl walked down the street toward me. She was gorgeous. She was dressed in some sort of restaurant uniform. Was it Sarah? I was sure it was. I went back to the website I had found her on. It was her. I was sure of it. She headed through the door that led to the apartment block. Fuck me, she was a fit-looking bird with a killer body.

Five minutes later, I got a text message.

‘Are you still coming?”

‘Yes. I am on your street’ ‘Good, come on up. The street door code is 5678. I am in flat six on the third floor, my flat door will be open, come on up, I will hit the shower, give me ten’ I finished my juice and paid my bill. A glance at the phone told me it had been eight minutes since Sarah had sent the text. I got up and licked my lips. I headed over the street and stepped up to her door. I used the keycode to enter the building.

My heart was racing. This was a step up for me. There was no lift, so I walked up the stairs to the third floor. The door to flat six was ajar. I stepped in.

“Hello...” I said nervously.

“Hi, close the door for me, please. I won’t be long. Go into the living room!” she shouted.

I went in, and it was well furnished. The window was open, and there was a nice draft. My heart was racing and palms sweating.

I heard a door shut, and then she came into the room. She was drop-dead gorgeous. She was dressed in a summer dress that showed off her legs and a vast expanse of freckled cleavage. her hips swaying as she closed the distance between us. She looked and smelled like she had just come out of the shower.

“Hi, you must be Zak?” she said, “Nice to meet you!”

She came closer and kissed me on the cheek.

“So what are you looking for, darling?” she said, her smile making my knees go weak.

“Hi ... Errmm, sorry, I am new to this, so I guess...” I stuttered,” I am a little bit nervous to tell the truth!”

“It’s cool, just relax, remind me, just how long did you ask for, two hours, wasn’t it?” she asked.

“Yes...!” I said and handed her the agreed fee. She put it on the living room table.

“Look, Zak, we all have needs and desires, so how about we just go into the bedroom and see what happens.” She said, and her hand stroked my chest.

“That sounds good to me!” I said.

“And just do what you feel you want to do, and if it’s something I don’t like, I will tell you!” she said and reached for my hand.

She led me into her bedroom but left the door open. She closed a window that had been open. She pulled the curtains closed.

“Please don’t be nervous. I’m gonna make this unforgettable for you.” She smiled.

She stepped back, hooking thumbs into her dress straps. She peeled it down inch by inch, teasing, revealing smooth alabaster skin. It dropped to the floor, and she stepped out of it. She was wearing white lacy underwear. A lacy bra that was just about controlling her huge tits and a pair of lacy panties. She gave me a three-hundred-and-sixty-degree twirl. Her panties were actually a thong; she had a great ass.

Her massive natural breasts strained against the fabric, nipples already poking through as big as wine bottle corks.

“You like?” She asked.

“Oh yes, you are gorgeous!” I replied.

“Why, thank you, sir, so you like what you see?” she smiled.

“Oh Fuck me, yes...!” I stammered.

She laughed softly, a sound that eased the knot in my gut a little.

“Relax, baby. Let me take care of you.” She smiled.

Her fingers trailed down my arm, she took my hand in hers and lifted it to her breast.

“So do you like big boobs!” she giggled,” I guess that’s why you booked me?”

I stroked her boob through the fabric of her bra. She smiled at me as I stroked her boob. Then, with a wink, she turned around. I didn’t need an invitation. I unclipped her bra, and she shrugged it off. My hands slipped around and cupped her huge tits as she dropped her bra to the floor.

Her nipples seemed to grow harder as I fondled her firm, young titties. They felt so big in my hands.

“Fuck me, they’re huge.” I purred.

“And they are all natural, just for big boob-loving boys like you.” She giggled.

My mouth watered. My cock grew hard as she wiggled her butt into my groin.

“I am feeling a bit overdressed. Would you like me to undress you?” she purred.

She didn’t wait for my response, she spun around, and my eyes dropped to her amazing tits, they were so huge, full and firm and begging to be sucked.

“Oh shit,” I gasped.

“They do have that effect on men!” Sarah giggled, and at the same time, she slid her hand down to cup my bulging crotch. I gasped as she rubbed my cock.

“Let’s get you naked!” she smiled.

I slipped my t-shirt over my head and kicked off my shoes at the same time.

“Mmmmm, a nice hairy chest, I love a hairy chest!” she said, and she leaned in and kissed my nipples. I gasped as she nibbled them gently. That made her giggle. She was a giggly girl. A real girly girl.

“Do you like kissing Zak?” she asked, lifting her head from my chest.

“Yes ... Yes, I do!” I replied, I was amazed at how relaxed I felt in her company.

She pressed her body against mine. Her tits mashed into my chest, soft and warm. Her lips found mine, and we were soon French kissing, lips mashed into lips, tongues fighting. I reached around and cupped her bum as she started to grind her groin into mine.

After a few minutes, she stopped the snogging and pushed me away, her hand slid down over my groin, stroking my erection through the fabric of my shorts.

“Your cock feels nice and hard, let’s release him!” she said, her eyes winking.

I groaned my approval, nodding frantically.

She sank to her knees right there on the plush carpet, her face level with my zipper. Deft fingers unzipped me, tugging my shorts and boxers down. My cock sprang out, rock-hard and throbbing, pre-cum already beading at the tip.

Sarah licked her lips, wrapping one hand around my shaft, stroking my dick slowly.

“Mmmm, so nice and thick!”

She leaned in, her tongue flicking out to lap at the head, swirling around the sensitive underside.

It had been a while since I had had my cock sucked. She licked up and down my throbbing shaft.

Jolts of Electricity shot through me. I felt my legs turn to jelly.

She stopped licking my shaft.

“Would you like to sit on the bed?” she asked.

I didn’t reply. I just sat on the edge of her bed, and she shuffled into position between my open legs. She glanced up at me and smiled; her fingers flittered over my cock and balls. I gasped. She giggled.

She bent forward, and her full lips parted, sliding over my bell end, sucking me deep into her mouth. She held me between her lips, not moving. Then she started to drag her lips up and down my shaft.

Her mouth was hot, wet velvet, tongue pressing flat against my length as she bobbed her head. She took me deeper and deeper, slurping noisily. Then she let my cocks crown slip from between her lips.

“God, I love sucking cock!” she said as she licked her lips. She moaned around my cock; her left hand was fondling my balls. Up and down her head bobbed, dragging her lips up and down my throbbing rod. I just sat there and enjoyed the show, the sensations radiating through my body.

She took me deep and held me there, saliva dribbling down over my balls. Then she slowly, god oh so slowly dragged her full, red lips up my shaft. Then she was kissing and suckling my bell end. Then she was sucking harder, tongue swirling expert circles on the ridge of my mushroom-shaped helmet.

Then she rubbed my shaft over her downy cheeks as she licked and kissed my balls. My heart was hammering in my chest, and I could hear my own moans and groans echoing around the room.

She popped her mouth off my dick, taking a breather, strings of spit connecting her lips to my glistening shaft. She grinned up at me.

“Mmmm Mmmm, you taste so good. You gonna cum in my mouth first, or save it for my pussy?”

“Is it okay to cum in your mouth?” I gasped.

“Yes ... I love to make a guy cum by sucking him off!” she smiled.

She wrapped the fingers of her right hand around the base of my shaft. Then she licked her lips and slipped them over my broad bell end. She bobbed her head up and down, but only moving up and down the top three inches of my cock.

I panted, too close already. I wanted to make this blow job last forever, but I knew I would not be able to hold back.

“I am going to cum, Sarah, I am so close!” I cried out.

She hummed approval. My knees weakened; I’d never felt anything like this. Her free hand fondled my balls, rolling them gently, urging me on. I couldn’t hold back much longer. I held her head, and my hips moved, thrusting my cock into her warm, willing mouth.

My cock was going deeper and deeper into her mouth.

She moaned louder, the sound muffled by my cock buried in her throat.

I felt my balls tingling. I knew all hope was lost. I knew any second now I was about to empty my balls into her mouth. She must have sensed how close I was and slipped her lips down my shaft until I was balls deep in her mouth.

“Oh fuck yes...!”I growled as my dick jerked and my balls unloaded themselves. Six strings of man juice exploded out of my cock. Sarah didn’t break stride; she just kept going deepthroating me like a pro. She took my load and swallowed it, not wasting a drop.

After another few seconds of oral action, she let my cock slip from her lips, and she smiled at me,

“How was that for you?!” she asked, “Did it get rid of those nerves?”

She stood up, and her boob were just there waiting to be played with. I cupped them in my hands; they overflowed my palms, so soft yet firm—I squeezed, thumbs flicking her nipples.

I slipped my lips over one of her brown teats. My hands fondled the firm flesh as my lips and teeth teased her nipples.

“Yes, suck my big tits!!” she giggled.

I licked and kissed her big tittes, I rubbed the firm flesh over my face. Sarah was purring as I worked on her big jugs. I nibbled on her nipples. I licked up and down her expansive cleavage. They were so firm, so full.

It was Sarah who moved things forward. She pulled away from me and stood up, shoving me back onto the bed. Her thong hit the floor, revealing a shaved pussy, lips puffy and slick with arousal.

She opened a drawer in the bedside table and pulled out a box of Durex. She pulled a foil-covered condom out and put it on the bed.

“I think it’s time you fucked me!” she smiled and looked at my semi-flaccid dick. She reached out and stroked it.

“I don’t know about you, but I am horny as hell!” she giggled.

It didn’t take long for my cock to react to her ministrations. As soon as I was hard, Sarah used her teeth to open the johnny, she rolled it over my erection.

She climbed onto the bed, straddling my hips, guiding my throbbing cock to her entrance. The heat of her pussy kissed my tip, then she sank down, inch by inch.

“Fuuuck,” we both groaned in unison.

She was tight, soaking wet, walls clenching around me like a glove. Instinctively, my hands clamped on her hips. The view of the gorgeous, busty girl sitting on my dick was amazing. She didn’t move for a few seconds. The smile on her lips and in her eyes told me she was either having a good time or was a great actress.

Sarah rode me slowly at first, grinding her clit against my pelvis, those huge breasts bouncing hypnotically, rhythmically. Her hard nipples drew my eyes to them. She soon moved up the gears. Riding me, shagging me, fucking me ... Her body was slapping down onto mine as she lifted and dropped, lifted and dropped.

“Mmmmm, your cock feels so good in my pussy!” she purred.

 
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