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My first Crossdresser - Part Three

My First Masseur - Part Three/Conclusion

... For the next three years, "Bob" was in my life on a bi-weekly basis.

As he rubbed and relaxed me ... . It was when the wet towel went over my eyes that my cock immediately boned. The first time I took his ... and a large amount. At first, he spit my cum load out into a towel but eventually swallowed all of my boy... Continue»
Posted by lovearub 3 years ago  |  Categories: Fetish, Masturbation  |  
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My first Crossdresser - Part One

... to crossdressers, one of my fantasies. I've never played it out." She was sipping her drink, and without ... When she walked in to the restaurant I knew I was in trouble.

It was the end of three long days ... video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's... Continue»
Posted by abend 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
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My first Crossdresser - Part Three

... Harrah's was crowded, loud, and bright. She walked in front of me, holding my hand and leading us ... playing was "Singing In The Rain", but to be honest, my head was spinning with lust and emotions so ... it's hard to remember. I put my arm around her and she leaned her head on my shoulder. We didn't speak... Continue»
Posted by abend 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
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My first time with another crossdresser.

... masturbating. and in the last story was my first time being with a woman wile crossdressed. now ... this story is about my first time with another crossdresser at the age of 18.

it was a friday night ... to come." we parted and i went out to my truck and got on the phone with johnny, set up a time... Continue»
Posted by sissypantyhoseboy90 4 years ago  |  Categories: Fetish, First Time, Shemales  |  
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The Long Road To My First BBC part three

... slowly his rock hard masterpiece approached my open and waiting mouth. As the bulbous head parted my lips ... not lose a single precious drop of his cum. The first blast hit the back of my throat almost causing ... the GH. Somehow that caused a shiver of excitement rush thru me like electricity. The light from my... Continue»
Posted by proudman2 11 months ago  |  Categories: First Time, Interracial Sex, Shemales  |  
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Making of My Sissy (Part Three)

... One day I was home to see, first hand, how my sissy's day progressed. The day went as I thought ... satisfaction through other sources. I invited them to the house to see and hear from my sissy first hand.

... it would, well planned and a perfect schedule to keep my little one busy. Then there was a knock... Continue»
Posted by sissymishel 3 years ago  |  Categories: Fetish  |  
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Part Three - My Secret is Shared

... was with while we were dating and three in the first four years of our marriage. My guess ... Part 3 – My Secret is Shared

“I have a hard ... is there are probably more that I am not aware of. The point is my wife is a slut. She likes sex... Continue»
Posted by jenniferlikesmen 5 months ago  |  Categories: First Time  |  

My first crossdressed cocksucking (true story)

... up my bum all prepared for ... anything.

The most stressing part was in the hotel, when i came ... for the first time in my life.

He invited me in, tried to make me feel more comforable. He also had some ... that first naughty experience.

It really didn't take long for me to unzip my jeans and drop them... Continue»
Posted by kamislut 2 years ago  |  Categories: First Time, Gay Male, Shemales  |  
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Beginnings: My First time as a crossdresser (PT 1)

... practice from borrowing my mom’s from time to time. When we got over to the mirror I took my first ... ). At first I was repulsed, I had never kissed a guy before, but the weed and the alcohol lowered my ... way up and down the shaft. This wasn’t my first rodeo so soon I was sucking like a pro, stopping... Continue»
Posted by sbobbi66 1 year ago  |  Categories: Anal, First Time, Shemales  |  
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My first Crossdresser - Part Four

... motionless for a moment, and then slowly began to strip. First her blouse, unbuttoned very slowly ... failing miserably at hiding her erection.

She bent down and undid my belt and pants, pulled them ... down over my legs and tossed them across the room. She tugged my boxers down as well, my cock happy... Continue»
Posted by abend 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
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My first Crossdresser - Part Two

... me her plan. "I told you that we were going to play it my way, so here it is. Ever since the first ... again saw just how sexy she was, and for the time being my discomfort took a back seat to lust ... with a nod, and said "I forgot to tell you, my room isn't here at the Sahara. I stay at Mandalay Bay... Continue»
Posted by abend 5 years ago  |  Categories: Fetish, First Time, Shemales  |  
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My Mum, the model - part three.

... my virgin arse to three hunks. I’d almost let Mark have it last night, almost. I still wasn’t sure ... . There were three, no four other girls on the set, they’d be background, but wouldn’t take part in the sex ... me, the three guys stood waiting, stroking their erections. I spread my legs, allowing Mark to push... Continue»
Posted by SFS 5 months ago  |  Categories: Anal, Taboo, Hardcore  |  
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My First Three-Some

... Some years ago, when I first started my education in aviation maintenance, I befriended a goofy ... ”. For the first time in my entire sexual life, I was orgasming (full body, out-of-this-world orgasms ... the first guy to ever attempt slapping me in the face during sex).

“We were in my SUV, he... Continue»
Posted by itsmerachel 1 month ago  |  Categories: Anal, First Time, Group Sex  |  
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Slippery Susie: My XXX MILF (part three)

... alone with her husband, Mike, for the first time since she
had cheated on him with three guys now ... Slippery Susie - Part 3 - Back at Work (Susie, Kerry & Jake) MFM

Only 15 minutes had passed ... and ready for more.
“You better run up and stick that thing in my s****r before it goes to
waste... Continue»
Posted by StCroix1960 1 year ago  |  Categories: Group Sex, Mature, Hardcore  |  

My first time crossdressing for a friend

... smiled and said ok pleas fuck me first, and reached for my purse wich i had put my cigarettes and a tube ... swallowed it all down it burnt a bit but i loved my first tast of cum. I set back up and finished my ... had.

thank you hoped you enjoyed reading about my first time. if you liked it let me know and ill wright more.

debby r.... Continue»
Posted by deborah_riggs 5 years ago  |  Categories: Anal, Fetish, First Time  |  
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my dad part three

... My Dad
Part three
After a short time lying there I got up and went for a pee in the toilet, as I ... cock, as I was doing this with my hands I slide them down the remaining part of his trunk to those ... a little part of his nob, I slide a little further into the water and I could feel it around my... Continue»
Posted by Ekaterina 5 years ago  |  Categories: Hardcore  |  
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First Time Crossdressing with a mate part 1

... about meeting another crossdresser for some horny mutual fun. I had been faithful to my girlfriend ... crossdressing occasionaly when we had sex, so I felt comfortable telling her about my secret fantasy.

I ... to gulp twice just to clear my throat, and her cock kept squirting for ages. As I felt the first shot hit... Continue»
Posted by obm_cd 1 year ago  |  Categories: Fetish, First Time, Shemales  |  
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My brown beginning part three

... and she took my cock in her soft hands in mere seconds I was having my first orgasm and shot cumm all ... so this is my first experience with real women.Mom and Gram laughed.Gram replied you ate my pucker ... I could see from my position grandma fingering her pussy i saw a white slick substance on her... Continue»
Posted by sadie56 6 years ago  |  Categories: Fetish, Mature, Taboo  |  
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My first time with a girl - Part Three

... yes, I got out of bed and stood near her.
My top came off first, then my bra. Louise was right ... ideas. I wanted to lick Louise like they did in the videos I saw. I wanted to put my hands inside ... boobs were there, I saw the hair between her legs too.
While Louise was in the shower, I closed my eyes... Continue»
Posted by sarahyork 5 years ago  |  Categories: First Time, Lesbian Sex, Voyeur  |  
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Mutual masturbation: Part Three "Can I use my

... Mutual masturbation: Part Three "Can I use my mouth"

 It was only a couple of days before we ... started cumming, my hips pumping my cock upward into his tight fist.

 The first three streams ... him to his room. I was unpacking my overnight bag when he said he wanted to take a shower... Continue»
Posted by Theo35 11 months ago  |  Categories: First Time, Gay Male, Masturbation  |  
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