If you've read the first in this series, you'll know I am Emma, and ex high-school slut that now commands a very good position with a big legal firm in the heart of then city. I recently met young Liam a chap who works in out IT department at a party dressed as a slutty girl, a real sissy. I wanted to know his story and so now I had the young Liam standing bollock naked in front of me, his slender 4.5 inch dick standing out rock hard, not very proud as it was too small to be proud, but it was definitely dripping pre-cum as I, Emma a very hot sexy 29 year old woman, sat, fully dressed in front of him waiting to hear him tell me about his 'sissy' cuckold life with his beautiful girlfriend Cassie.
The Sissy, Liam Harper
His face was refined, with symmetrical features and full, soft lips that lent him a "pretty boy" appeal, making his look both striking and memorable. His lean body was toned but not overly muscular, highlighting more of an athletic, slender build that suggested agility and balance. He carried himself with an easy confidence, his appearance balanced between softness and strength. His style was casual but polished, fitting his effortless charm and natural beauty. Altogether, his look blended masculine and feminine appeal, giving him an androgynous quality that was captivating and unique, drawing attention wherever he went.
And his rather mean young girlfriend, Cassie Bennett
Her brunette hair fell in natural waves, framing her expressive, hazel eyes that revealed determination and focus. Her 34B bust added balance to her athletic figure, lending femininity to her strong, well-defined upper body. She embodied both softness and strength, a blend of curves and muscle tone that reflected health and vitality. Whether dressed in workout gear or everyday clothes, her posture and the confidence in her movements made her presence noticeable. Her skin, likely with a subtle sun-kissed glow from outdoor activities, completed her look as a true gym enthusiast, living the lifestyle of discipline, energy, and passion for physical well-being.
This is his story:
The first time Cassie dressed me up I didn't even realise I was being dressed as sissy. I thought it was just fancy dress, until I got to the party and realised, I was the only guy there dressed as a girl. We had gone to a friend's party, and it was supposed to be 'Pimps & Tarts'. Of course, Cassie insisted on being my pimp. I didn't realise this was going to become a new lifestyle.
Cassie had dressed in a 'Gangsters' expensive track suit, with the bottoms hanging around her ass. But instead of wearing boxers, she had on a very skimpy little thong which was completely on show above the low hanging tracksuit bottoms, which also showed off half her incredible round booty. Below the jacket she wore a very tight skimpy vest top with no bra. Her beautiful 34B very perky breasts were very much on show, with her nipples making sharp points through the thin material. She also wore several heavy gold chains and a beanie around her gorgeous brunette curls.
For me Cassie had dressed me, against my many protestations, but Cassie always gets her way, especially when she takes my slender dick in her hand. The first thing she did in the afternoon was make me take a long bath, then she came in and we spent an hour shaving and waving all of my body hair. I argued against it, but she insisted on even doing my ass crack. When she finished, she spent another half hour smoothing in body lotion all over. My dick was throbbing. She told me that if I behaved myself dressed exactly as she wanted me to, then she would wank me off before we left for the party.
So, she had got me to squeeze into one of her little pink thongs. I was very surprised how comfortable it was; the little triangle of material cupped my little dick and balls very nicely. The she had bought me a very short white mini skirt, more of a micro-mini as it barely covered my round bubble butt, leaving the lower moons fully on show. The pink thong clearly visible above. It was very girlie. The she had bought me a matching pink to bra, and a see-through white crop top that left my flat stomach on show. To round off the outfit and to show everybody I was her 'tart', she fixed a pink dog-collar around my neck and had a pink leash. She did some very light make-up, mainly eyeliner and thickened up my eye lashes, but added pink lipstick that matched the pink of my skimp underwear. She gave up on getting me to wear heels as she didn't think that I would learn to walk in them in time but bought me a very cheap pair of pink trainers. When I checked in the full length mirror I was horrified to see just how pretty I looked transitioned into this slutty girl.
Once we were both dressed, she took me back into the bathroom. "You've been a very good boy, so, slut, as your pimp I get to wank you off." She stood me in front of the mirror and told me, "She's hot isn't she," pointing to my refection. Pulling my hard dick out from the little pink thong, she started to stroke, "Tell me baby, would you fuck a hot girl like this? Would you bend her over and push your dick into her boi-pussy?" I felt so fucking humiliated and so fucking turned on. I'd never had any gay feelings. Yes, like anybody, I'd always been curious about the other guy's cocks in the showers after football. But that was normal curiosity. We all want to know how we compare to others. I had a very intense orgasm shooting my load into the loo.
My beautiful Cassie ordered us a taxi to take to the party and I went to put my coat on, and I commented that it'll make it look like I'm naked underneath.
Cassie: "Baby, you're not wearing a coat, you're coming to the party as you are."
"I can't walk don out to the taxi dressed like this and then let the taxi driver see me. I'm dressed like a teenaged slut, a middle-aged man's wet dream."
Cassie: "It's fancy dress, babe. People will understand your in fancy dress." Then with a naughty glint in her eye, "Do you think if you give the taxi driver a blowjob we wouldn't have to pay."
I knew she was joking; I thought she was joking.
"I'm not sucking any cock, baby, even if I am dressed like a cock-sucker."
Cassie, still with that slightly naughty glint, "Are you sure, you look like a naughty cocksucker to me," And as we went out of the front door, she gave my ass a very hard slap.
Cassie; "Ooooh! Naughty, I can see the red mark on your cute ass."
"No way! I hope not."
To my horror, when we got outside and the stepped up to the taxi, she reached for the door handle opened the door and indicated for me to step in first, as I did so she gave my other cheek a very hard slap. The driver turned and smiled knowingly at me then turned away when he twigged I was man. I was so embarrassed. When cassie was in beside me, she noticed and said, "Oh baby! Now all your cheeks are bright red," and gave a very naughty laugh. She was really enjoying the power this gave her. Literally the boot was on the other foot.
Cassie leaned into me and whispered, but quite loudly so there was a very good chance the driver would hear, "Move into the middle and open your legs flash him your little pink panties."
I looked at her and vigorously shook my head.
Cassie: "You're such a spoil sport." Then she leaned into me again and whispered so that the driver definitely couldn't hear, "if you don't do as I say when we get to the party, I'll leave you outside and you know where it is? It's a rough neighbourhood, when I eventually come back to find you, we'll see how many of the local thugs have raped your ass and mouth."
Humiliatingly I slid into the middle of the seat and opened my legs. The skirt was so short that with my legs open it was like it was just a little belt. My thong barely covered little dick was fully on show. I met the eyes of the driver in the mirror. I knew with the angle of the mirror he wouldn't be able to see anything below my chest. We looked at each other for a few seconds then he reached up and angled the mirror down so he could see my little pink thong.
