This is a true story about my first time with a TS and my first time taking a real cock.
There is a street in Liverpool that is made up of mainly apartments and serviced accommodation. My old client was based down south and asked me as a favour to check on his short term let flats every 3 months as he thought the agents were ripping him off with unnecessary repairs. One afternoon I went over to check on his flats and rang the buzzer, they had been told I would be by. No answer so I let myself in. As I was in there a South American lady turned up and was speaking in Portuguese on her phone. Clearly flustered she told me in broken English that she had left her other phone in the last flat on the other side of Liverpool in Southport.
She was about 5’6”, casually dressed and with a big bum and boobs. I offered to take her to pick it up. She was grateful so we jumped in my car and chatted on the way.
That’s when I learned she was a TS not a lady. And also working from the flat if that makes sense. I explained what I was doing there and she panicked thinking I might tell my client and have her booking cancelled. She pleaded with me not to call him and before I could reassure her it wasn’t any of my business she offered me some time with her that afternoon when she had no bookings to buy my silence. I wasn’t going to turn that down. We got her phone and arrived back at her flat on Henry Street. She said to give her 30 minutes to freshen up so I went to the Bridewell pub for a bit of Dutch courage… |
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I was buzzed in and made my way up the stairs.
She was wearing gym stuff and her figure was unreal. Tight leggings and bra top showing her big cleavage and her curves. No sign of her surprise, clearly well tucked away. I was so nervous. I was shaking when she walked up to me and kissed me softly. She laughed nicely as how nervous I was. She said don’t worry I will be slow and gentle, then added “at first” and winked at me. She undid my zip through hoodie and dropped it to the floor before removing my t shirt and nibbled on my sensitive nipples. She told me to get a shower and come out in a towel. My head was spinning. I’d thought about a TS so many times and always bottled it.
I came out of the shower room, towel round me. There was a big towel on the bed and on the bedside table was a scattering of condoms, a bottle of oil, a tube of lube and three dildos all different sizes.
“Lie down on your tummy and I’ll give you a massage to relax you…”
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She massaged me gently. Stroking up my thighs and brushed my balls and ran her fingers over my arsehole.
From nowhere the tone changed very quickly. She pulled my hair back and said in my ear “are you a virgin?”
I said yes a clear tremor in my voice.
“Good, I like tight ass”
She pushed my face down and straddled me still in her Lycra. That’s when I first felt it. Her cock was hard and was now pushing into my arse and I could feel it pressing between my cheeks.
She turned me over and still straddling me moved up my body. Her crotch was inches from my face and I could see her cock pressed against her in the the tight, thin, pink leggings. It was big. Maybe 8” and I could clearly see the outline of her cut dick. It twitched and I saw it swell some more as it did. She stood up and peeled off her top, her fake tits were nice and her toned, brown stomach had the makings of a six pack. She stretched her leggings down and over her white Nike trainers that she kept on. Weird how I remember that part so clearly.
Her cock now pointed straight out from her petite but curvy body. It looked even bigger and it was a darker shade of brown than the rest of her body.
“Have you sucked dick before?”
I nodded.
“Good, let’s see how good you are then”
I knelt down in front of her and gripped her shaft before taking the tip in my mouth and swirled my tongue around it. |
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"This is a true story about my first time with a TS and my first time taking a real cock.
There is a street in Liverpool that is made up of mainly apartments and serviced accommodation. My old client was based down south and asked me as a favour to check on his short term let flats every 3 months as he thought the agents were ripping him off with unnecessary repairs. One afternoon I went over to check on his flats and rang the buzzer, they had been told I would be by. No answer so I let myself in. As I was in there a South American lady turned up and was speaking in Portuguese on her phone. Clearly flustered she told me in broken English that she had left her other phone in the last flat on the other side of Liverpool in Southport.
She was about 5’6”, casually dressed and with a big bum and boobs. I offered to take her to pick it up. She was grateful so we jumped in my car and chatted on the way.
That’s when I learned she was a TS not a lady. And also working from the flat if that makes sense. I explained what I was doing there and she panicked thinking I might tell my client and have her booking cancelled. She pleaded with me not to call him and before I could reassure her it wasn’t any of my business she offered me some time with her that afternoon when she had no bookings to buy my silence. I wasn’t going to turn that down. We got her phone and arrived back at her flat on Henry Street. She said to give her 30 minutes to freshen up so I went to the Bridewell pub for a bit of Dutch courage…"
I'm in Southport and this never happens to me! |
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She held my head and pushed her cock into my mouth. I could only get just over half of it in and she started to slowly thrust fucking my mouth. She held my hair tight and slapped my hands away as she fucked my face her cock going deeper as I throated her fat shaft.
She pulled out and moved me to the bed telling me to lie on my back with my head over the edge of the bed. She squeezed my nipples hard as she started to plough my face, her balls slapping on my chin. Every now and then she reached down tugged on my hard dick a little and gave my balls a little slap making me wince.
Turning round she spread her cheeks wide and pushed back on to me demanding I rimmed her fat Brazilian ass. Then she would turn round again and start relentlessly smashing her cock into my throat. |
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She pulled me up and clearly gauging how submissive I was for her she took her phone, pulled my hair and pushed her cock in my face. She snapped a pic and said “now I know you won’t be telling anyone, like a dog for me now”
I got on all fours and felt her spread my cheeks. She looked and said “mmmm tight boy, this might hurt a bit, but you will like”
She flicked her tongue out teasing my exposed hole with it. I moaned in pleasure. She spat on it and then I felt the pressure of her finger at my opening. She squirted some lube on my hole and then her finger teased my anus before she slowly pushed a single digit inside me. I groaned as she started to slowly fuck me with her middle finger as she twisted it and worked it gently in and out. Soon the finger became two and she opened them a little trying to open me up for what was to come.
“You are ready for a toy now” the first toy was about 5”, a modest looking life like white cock with veins and a small helmet. I bit down on the pillow as it entered me. She was slow again at first. “Breath in, deep” as I took a big breath in and relaxed she pushed the full length of it into me. I felt a kind of popping sensation and it felt like it burned a little but it wasn’t agony, just a tad painful. She held it in me and told me to breath. Soon she was moving it around, more side to side than in to out. Then she slowly took it out until just the tip was in me. Then she plunged it into me. And out. And in. Fuck it hurt at first but soon I was into it.
“Very good, I want to see you ride it though”
She took it out and I saw it had a plunger base. She spat on it and stuck it to the laminate floor.
“Now ride that cock like your wife rides you, like a whore.”
I knelt over it and positioned myself over it. I found my hole with the tip and let out a gasp as I slid onto it. It was easier than from behind and soon I was able to get a steady rhythm going. Up and down.
“Ride it hard and suck my dark cock” she stood up and positioned her dick by my face. I opened my mouth and took as much as I could sucking her as deep and fast as I could ride the rubbery dick. She made appreciative noises and every so often would slap my face with her hard dick.
“Mmmm now lick my pussy”
She bent over and touching the floor pushed her ass into my face. I spread her cheeks, rubber cock balls deep in me, and buried my face in her ass. Her hands were palm down on the floor as she pushed herself back onto my eager tongue. |
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