Transvestite Model, Escort,
Companion & Fitness Mentor
A Short Story
By John C., Penn, USA
Fancy a quick one? Enjoy this short story from the pen of John C.
Upholding the great tradition of erotic fiction with the added twist of the latest AI-generated artwork. But are they really fiction? You decide!
Story 6 - Alessia, Alison & Audrey
Alessia upstaged by Broadway Star?
Great short story about a Broadway star in need of some sex education lessons. Who better to provide those than Alessia!
Alison entered the large lounge of her mansion and said “Hello” to Rod, ”I’m glad you’re staying with us. After dinner we’re having some people over for drinks. One of them is Audrey Brown, the famous Broadway actress.” Audrey is short, about 5’2”, very thin, about 90 lbs. She was a loner and it was well known that she had never had a boyfriend or girlfriend. Being named Audrey was very coincidental as she resembled Audrey Hepburn, the famous actress who was popular in the 50’s and 60’s. Alessia had never understand Audrey Hepburn’s popularity. It was hard to understand how men could be attracted to her. The other popular actress in the 1950’s was Marilyn Monroe. Marilyn was a sexpot, until she spoke. Her voice was that of a pre-teen age girl. It was as if American directors couldn’t deal with Marilyn’s overt sexuality, they forced her to speak like a pre-teen to minimize her overwhelming eroticism. Audrey Hepburn was different, she was like someone’s 14 year-old sister. Yet she was very popular nevertheless.
Most of the guests arrived about 8 o’clock. Audrey, true to her star status was the last to arrive, getting there at 8.45. All of the guests flocked around Audrey, she was highly successful and famous, the critics loved her. This was an unusual situation for Alessia. Usually, when Alessia was at a party, the guests flocked around her, her animal magnetism ensuring a constant stream of admirers. Now however, nobody was paying attention to Alessia. Audrey was going to pay for this!
The party broke up about 11pm, and Alessia introduced herself to Audrey. Alessia wore a short blue skirt, exposing her beautifully smooth tanned legs. Alessia is 55 years old, but looks much younger. Her addiction to physical fitness resulted in her awesome tight body, long distance running and physical training, produced a perfect body. Audrey had always had little to no interest in sex, but as soon as she set eyes on Alessia that changed. She couldn’t take her eyes off Alessia’s full, firm lips and desperately wanted to kiss her, she found Alessia’s beauty and raw sexuality was overwhelming. When she was 16, Audrey had been seduced by a female art teacher, but after a brief affair, the teacher rejected her. This devastated Audrey, and resulted in her not getting involved with anyone sexually.
As Audrey and Alessia talked, Audrey’s started to feel a warm ache in her groin as her pussy became moist, something that hadn’t happened in years. “Would you come to my room Alessia? I’d like your opinion on some new clothes that I purchased.” As soon they entered the room, Audrey could not restrain herself and she turned and she kissed Alessia passionately full on her rich red lips. Alessia was still angry with Audrey, jealous of all the attention Audrey had received. Alessia was going to make love to Audrey, but she’d teach her a lesson at the same time, and she had an idea how.
Alessia had Audrey just where she wanted her. “Undress me” Alessia said. Audrey had never felt like this before. Audrey’s pussy, dormant for years, was now like a volcano. Audrey had no idea that Alessia was trans. Audrey removed Alessia’s clothes, and was shocked to see that Alessia did not have a pussy, but a superb, huge, thick cock. Audrey was almost totally inexperienced sexually, except for the brief affair with her teacher. “Let’s get in bed” Alessia demanded. “Take your clothes off, I want to see you nude”, Alessia said. Alessia then said, “Lie on your stomach. I’m going to lie on top of you, and massage your body with my cock.” Audrey did as she was told, she wanted to please Alessia, anything else in her world was now meaningless. Audrey lay on her stomach, her boy-ish ass exposed. “This is going to be like fucking a teenager”, Alessia said. Alessia got on top of Audrey, and rubbed her superb cock over Audrey’s thin, boyish body. Alessia had always been attracted to busty, tall Amazon types. She had never made love with a thin, delicate girl.
Alessia used her superb cock, to massage every inch of Audrey. Alessia concentrated on Audrey’s ass. With minimal stimulation, Alessia thrust her cock into Audrey’s small ass. Audrey shrieked in pain, her screams were heard in the adjoining bedrooms. This was a harsh introduction to sex for Audrey. Despite the pain, the pleasure of being fucked by Alessia was tremendous. Audrey wished that the fucking would never end. Alessia is a superb lover, she thrusted faster and faster. It was like Alessia’s cock was locked in Audrey’s ass, never to leave.
Suddenly Alison burst into Alessia’s bedroom, and shouted “What the hell is going on in here?” Alison was shocked to see both Alessia and Audrey nude, with Alessia’s cock locked in Audrey’s ass. Alison had been fantasizing about Alessia all day. Alison wanted to suck Alessia’s cock but the situation with Audrey changed everything.
As usual Alessia swiftly took charge. “I doubt that Audrey has ever even sucked a cock before. Certainly not one as impressive as mine,” Turning to Alison, Alessia said. “I want you to show Audrey how to suck cock properly and then share my cum. But first, I’m going to whip you Audrey. Alison, get me the bullwhip from the closet.” Alison dutifully retrieved a massive bullwhip from the closet and passed it to Alessia “Face the wall, with your arms above your head,” Alessia directed Audrey. Alessia started with gentle strokes, on Audrey’s back, exposed ass, and legs. She then concentrated on harsh strokes on Audrey’s boyish ass, Alessia’s cock began to stiffen again until she reached a full mesmerizing erection. No cock could compare with Alessia’s. Knowing what was required of her, Alison did not wait for any direction from Alessia but greedily grabbed Alessia’s pulsing cock, and enveloped it in her wet eager mouth.
Alessia dropped the whip, and allowed Alison to concentrate on sucking her cock. Audrey desperately wanted to suck Alessia too but Alessia commanded “You’re not ready to suck my cock yet, watch how Alison does it. Finally, Alessia came with a massive shuddering orgasm, shooting a huge, creamy stream of thick hot cum into Alison’s open mouth. Careful not to spill a drop, Alison turned to Audrey and they kissed passionately, exchanging Alessia’s hot cum with their tongues until they both could resist no longer and swallowed her cum greedily deep down into their throats.
After the intense session with Audrey, Alessia was really tired, and ready to go to sleep. Alex and Alison had a beautiful home, and Alessia’s bedroom was very large, with a beautiful view of the Atlantic Ocean. ”Why don’t you stay here tonight”, Alessia asked Audrey. This was just what Audrey wanted to hear. Audrey was becoming obsessed with Alessia. When Alison sucked Alessia’s superb cock, this was a tremendous turn on for Audrey. Audrey had very little sexual experience, but that evening completely changed Audrey’s life. Her film career did not seem important any more. Audrey’s pussy was dripping, it was like a lake, Audrey was desperate for Alessia to fuck her. When they got in bed, Audrey first wanted to suck Alessia’s cock. She had never sucked a cock before, but she had watched carefully Alison, and wanted to emulate Alison’s tremendous cock sucking skills.
“I sleep in the nude”, Alessia said. ”We’ll both be nude tonight.” Audrey was reluctant to shed her clothes, this experience was entirely new to her. On the other hand, Alessia eagerly dis-robed, she had no problem exposing her fine body. Alessia’s legs were long, lean and well-toned, her cock was superb, close to 8 inches, when flaccid. Alessia was semi-hard and really wanted Audrey to fellate her, but she wanted to seduce Audrey. Whipping Audrey was a tremendous turn on for Alessia, but also for Audrey. Audrey finally timidly removed her clothes, exposing a teen age, boyish figure. Finally, Audrey got up the nerve to stare at Alessia’s superb cock. She could not wait to suck Alessia’s cock, “Please let me suck your cock.” Audrey walked toward Alessia and knelt down in front of her and carefully filled her mouth with Alessia’s engorged member. ”Take it slowly”, Alessia said. Audrey finally established a rhythm, and Alessia struggled not to come, but managed to hold her orgasm for several minutes. Finally, Alessia let rip and exploded into Audrey’s willing mouth. “I want you to swallow all of it.” Alessia said. Some of Alessia’s cum leaked on to Audrey’s hand, Audrey licked this cum and swallowed it not wanting to miss a drop. “Let’s get some sleep“, Alessia said “ I suspect we’ll be busy tomorrow!”
After only a few minutes, Alessia and Audrey were in a sound sleep. Audrey gently held Alessia’s cock in her small hands. It was as if Audrey never wanted to let Alessia’s cock go away. After a few minutes, Alessia had a very intense dream. Alessia dreamed that she and Audrey were getting married. Audrey wore a tuxedo, Alessia wore a beautiful white wedding dress. Alessia had been sleeping on her side, but she was restless, and ended up sleeping on her back. While she was sleeping on her back, Alessia developed a massive erection. While Alessia and Audrey went to sleep quickly, Rod was having trouble sleeping. Rod was also obsessed with Alessia, but didn’t realize that Audrey and Alessia were together. Rod quietly entered Alessia’s room. Alessia awakened, Audrey remained asleep. Alessia whispered, “Be quiet , I don’t want you to wake up Audrey.” Rod kissed Alessia passionately, he was falling in love with her. “Let’s go to your room,” Alessia said and they quietly crept out, leaving Audrey slumbering. About 10 minutes later, Audrey awakened, Alessia was not there. Audrey had never masturbated, had never had an orgasm. But her pussy was wet, and she needed relief. Audrey began massaging her clit, this increased her intensity, and after several minutes, Audrey had the first orgasm of her life. Things were looking up.
