Disclaimer: Please do not read this story of sexual activity between a man and boy if it is illegal and/or socially or religiously unacceptable within the society or country in which you are currently situated. However, if you should decide to read it please do so with the awareness that you have chosen to do so of your own free will. The story is entirely fictitious and any resemblance and any resemblance to any person alive or dead is purely accidental.
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Little Ricky's Sissy Photoshoot
I guess you would call Little Ricky's family unconventional. His father was a porn actor, not really cut out for family life, who enjoyed taking his work home (or anywhere else) with him too much to have much interest in his wife and children. Ricky's mother, Tania, had been one of his father's co-stars. Her career had started in her teens, when her small breasts and skinny figure had made her a favourite with directors for her "jailbait" looks. She was good at her job and worked continuously for many years, the nature of the roles changing with the development of her figure, bringing home an income which kept herself and the children in a lovely house in some style. Of course, with time, the work slowed down and now, although she was still in good shape and knew how to look as seductive as ever, she earned a lesser living mainly from MILF movies, where she was usually seducing some unsuspecting young boy or girl.
Tania's current boyfriend was called Michael and they seemed to be made for each other. He had a voracious sexual appetite and a business which gave him a more than adequate income and she had a voracious sexual appetite and needed to maintain the lifestyle to which the family had become accustomed. They also got on quite well, which was nice. He worked hard and usually only came to visit at weekends, when he made up for lost time with Tania.
Having been brought up with just a mother and a sister, a man in the house was a source of fascination to Little Ricky. He was so different. Although he was into his fifties, he had a fairly trim body with hair in different places and Ricky liked to see his muscular body. Tania was very open about her sex life and Ricky often caught glimpses of them in various stages of undress and sexual activity. He was particularly fascinated by the older man's cock, which, from the little he had seen, was of enviable size, compared with the boy's twelve year old shrimp. When Tania used her charms on the man it grew impressively bigger, which Ricky frequently admired, it being often visible even when Michael was fully clothed.
Tania's openness also extended to the extra-curricular education that she gave Little Ricky and his fourteen year old sister, Dawn, particularly in her area of greatest expertise, sex. She advised her offspring not to waste too much time getting close to friends of their own age, who were immature in thought, deed and ability to smooth the siblings' path through life. There was much more to be gained in cultivating relationships with older people than themselves, from whom they could benefit in many ways.
At the school that Little Ricky and Dawn both attended, the girl practiced what her mother preached. Her dyed blonde hair and carefully applied makeup were those of an older female, but like her mother before her, her figure was still developing, so she still had the body of an adolescent. She skillfully manipulated the wasteline of her skirt so that hers was the shortest in the school. I'm not sure if there were regulations on the type of underwear to be worn by girls, but if there were, I don't think the tiny thong knickers that she wore strictly complied. The ensemble was completed by a tight fitting white shirt and the highest heels she could get away with.
Her appearance and attitude certainly drew the attention of the older boys, but she mainly reserved her flirtations and glimpses of bare bottom cheeks for the teachers, which seemed to be appreciated by all the male ones who were still alive and many of the females. How far this went was a matter involving total discretion, as pupil and teacher careers were at stake. Suffice it to say that her progress through school was smooth and her academic results sometimes surprisingly good.
Little Ricky was envious of her. Just by dressing and acting in this flirtatious manner, she could exert a power over people that he could only dream of. He wished that he could arrive at school wearing the clothes that she wore, but it seemed that this was definitely contrary to regulations.
For life outside school, she also had a wardrobe of provocative attire, and this had recently been augmented by several gifts from Michael, her mother's boyfriend, who then liked to take pictures and videos of the results. Being curious, Little Ricky watched with interest as this was sometimes followed by some kissing and mutual fondling. Tania did not disapprove, as she had been very similar at the same age, and anyway, it helped to cement the relationship between the family and its benefactor.
Again, Little Ricky was envious of Dawn in her increasing intimacy with Michael. When he was at the house, Ricky took to wearing tight little shorts that he had really grown out of, to see if they would attract any attention. The central seam parted the cheeks of his bottom nicely and the thin material did little to hide his neat little package at the front. The shorts seemed to have the desired effect, and he was pleased to see Michael's eyes often drawn to them. Ricky took to sliding onto the older man's lap, where if he moved in certain ways, he could feel the object of his desire, Michael's cock, growing to meet the wriggling bottom. When they had play fights, the boy would sometimes be able to touch Michael with his hand, which was very exciting. He was rewarded with increasingly frequent squeezes of his bottom and thighs, which in turn made his little cock spring to life.
One weekend, Dawn's school class had a geography field trip to the mountains which would involve an overnight stay. Although it was not compulsory, the geography teacher, Miss Updyke, was very keen that Dawn should go, assuring her mother that it was certain to be of benefit in terms of academic assessment. So, having packed some surprisingly inappropriate clothes, Dawn joined the other geography enthusiasts for the weekend trip.
This would leave Michael without one of his weekend play-mates and Tania hated to see him disappointed. Before he arrived, she said to Little Ricky: "Remember how much fun we had when we dressed you up in Dawn's clothes that time? You enjoyed that, didn't you?"
Little Ricky agreed.
"Why don't we give Michael a surprise," she continued. "Let's dress you up again and let him take some photos of you. I'm sure you would both have a great time."
This seemed like an excellent idea to Ricky, and his small cock demonstrated its approval by jumping to attention.
There was no time to lose and mother and son went to Dawn's bedroom where Tania selected some of the clothes that Michael had bought for Dawn. Little Ricky eagerly removed his boy clothes and savoured the feeling as he slid a thong up his legs, feeling the lacy triangle of material tight on his little boy bulge with the string at the back slipping between his cheeks and caressing his hole. Next, Tania handed him a tiny stretchy yellow skirt, not much more than a foot from top to bottom. Even wearing it low on his hips, it only just covered his bottom. Through the tight fabric you could see the outline of the thong disappearing between his cheeks, while the two side pieces were visible above the top of the skirt. On top, Ricky wore a small white shirt which had no buttons but which tied at the bottom. Tania assured him that it was no problem that it was quite clear that he was completely flat chested. "I'm sure that what Michael will want to see you as a boy dressed as a slut girl, not just a carbon copy of Dawn." Anyway, any illusion of Ricky being a real girl would soon be dispelled by the little bulge at the front of the tight skirt.
Tania helped him as he pulled a pair of white, hold-up stockings up his legs and the sensual feeling as they wrapped his legs sent quivers through his body. The ensemble was completed by a pair of strappy, white, four-inch stiletto heeled shoes, in which Little Ricky had practiced walking last time they played dress-up. He proudly stood up and admired himself in the mirror. Tania admired him too.
"Mmmm. Very sexy." She came over and kissed Little Ricky softly on the lips. "I could eat you up myself."
She gave the little package between his legs a gentle squeeze. "Oooh – good boy! I hope your little cock doesn't get too big and try to get out of your knickers!"
"Anyway, we haven't finished yet; there is still your makeup to do." First, she made Little Ricky's eyes up, using years of experience to give him long, dark, fluttering eyelashes that gave his eyes a large, appealing look. Then to his lips, where she applied a pink lipstick, around which she penciled a slightly darker coloured liner. She carefully coated the full, soft, lips with a layer of gloss. Ricky's hair, which was quite long, was adjusted so that the long fringe fell seductively over one eye. Again, he looked in the mirror to see a face that he found hard to believe was his own, it was so inviting with the big, bright eyes and mouth begging to be kissed or to be used as a tool of untold lustful gratification. The overall look was of a beautiful sissyboy-slut, purpose made to make any man rock hard at a glance. Little Ricky loved it.
They were just in time as they heard Michael letting himself into the house.
"Don't come up," called Tania. "I have a new model for you who is just getting ready. We'll be down in a minute."
Little Ricky's excitement was reaching unbearable heights, but before he was allowed to display myself, Mum had a few words of wisdom. "Just remember, you're a model. You've seen what Dawn does and how much Michael likes it and you've seen me modeling loads of times. If you copy that, you'll be the sexiest model ever! If Michael wants to kiss you or touch you, it's OK as long as you are completely happy about it. I'm sure he won't mind if you touch him too, if you want to. Just remember, fingers, lips and tongue. I think you know how to use them by now."
Yes, despite Little Ricky's young age, he had seen enough of his mother in action to have a good idea of what to do.
Carefully, he followed her downstairs, his heels clicking in a very appealing way with each step. He entered the lounge and there was Michael, relaxing on one of the two sofas. When he saw Ricky he sat up, a look of wonder crossing his handsome face.
"Wow, look at you!" he just managed to utter.
Tania spoke, directing her son: "Sit down – remember you are Michael's model for today. Michael, here's the camera. Ricky wants to be your sexy subject!"
She was right. That's just what Ricky wanted to be. He turned around slowly, sticking his bottom out, then bending over a little so that the cheeks were just visible. He heard the first of many camera clicks. He turned his head to face Michael over his shoulder, staring straight into the camera, his lips slightly pouting as he had seen his mother do so often in the past.
Michael was regaining control as he worked the camera. "Sit on the sofa," he said, indicating the one opposite where he sat. Little Ricky did so and sat with his legs slightly apart, so that the stocking tops and the white of the lacy knickers were visible. Michael stood up and started to circulate around the gorgeous boy, taking pictures from different angles and Ricky followed him with his eyes. He kept his mouth invitingly open just enough and licked his lips slowly, making sure that his pink tongue was clearly visible as he did so.
Next, Michael asked Little Ricky to recline on the sofa with one leg draped over its arm. His boy bulge in its lacy pouch was clearly visible as the skirt rode up. The man arranged the shirt so that it was creased in such a way as to show Ricky's little pert nipple. Again, Michael moved around him, taking photos from different angles as the boy pouted and licked his lips.
Tania had picked up the video camera and was recording the session. "Are you getting all this?" asked Michael and the mother confirmed that she certainly was. Then he sat next to Little Ricky on the sofa and the boy looked into his eyes, longing to be touched. Michael must have read Ricky's mind as he lent over and kissed the inviting, lipsticked mouth, his tongue slipping between the parted lips. The aroused boy tingled all over as he felt strong hands reach inside his shirt as Michael gently fondled his nipples, then he withdrew again and his hand moved down to the beautiful, stocking wrapped leg. The man's tongue continued to entwine with the boy's while his hand slid over the stocking to the soft, downy skin between stocking and paradise. Michael savoured the softness before gently moving to touch the lace covered bulge between the boy's legs, enjoying feeling how the penis, while small, had grown stiff and ready.
Little Ricky was in heaven, loving the attention he was receiving from the older man and aware of the affect he was having on him. All he wanted was to be the object of the man's desire – to do all he could to please him. He knew what he wanted to do and was pretty sure that it would also give Michael the ecstatic pleasure that he wanted to give. But he was shy and unsure how to proceed.
It was then that he heard his mother's voice encouraging him: "Touch him Ricky. Touch Michael's cock."
Little Ricky needed no further invitation to fulfill his own desires and do the thing that he knew in his heart that Michael was longing for. As they continued to kiss and as Michael continued to fondle the boy's fledgling cock and balls, Ricky reached over, slid his hand up the man's leg and onto the object of his fantasies – the overgrown, stiff penis, which he grasped through his clothing.
"Open his trousers," instructed Tania – an instruction that Little Ricky keenly obeyed. Michael rarely wore underpants for his visits to the family, in order to be ready for action immediately upon arrival. Today was no exception and as Ricky undid the button and slid open the zip, his cock popped eagerly out. Michael gasped in ecstasy as he felt the boy's small fingers encircle his swollen penis, breaking off from kissing and fondling Ricky as he sat back on the sofa.
The boy stared in admiration and awe at the long, hard member that he was caressing, but it wasn't long before his reverie was interrupted by the next words of wisdom from Tania.
"Kiss his cock. Take him in your mouth," she advised. Again, Ricky was the perfect student, doing exactly as instructed, and Michael watched in eager anticipation as the pink, glossy lips lowered to touch his aching penis. He could see the lips part and the tongue gently move to taste the tip, before the soft lips closed around the shaft.
By now, Tania was seated on the sofa opposite the action, still filming as she parted her legs and slipped her hand into her knickers. This was turning her on! In the camera's screen was Little Ricky's bottom pointing upwards as his mouth gently began to move on Michael's extra-stiff cock. In the foreground, the high-heeled shoes were provocatively prominent while the stockings added to the sluttish look. The tight, short skirt partially covered the boy's tight little cheeks. The man's hand reached out to fondle Ricky's stocking covered leg then moved up to his pert bottom, squeezing it gently before the fingers slipped under the piece of the thong between the cheeks and gently caressed the delightful hole. Michael's other hand went to the front of the boy's lacy knickers cupping the sweet little package before slipping his fingers inside the pouch.
Little Ricky hair fell over his face and onto the man as his wet-look lips continues their motion on the man's shaft. His tongue explored the head of the penis and his little fingers moved up and down on the shaft in time with his mouth. Ricky's undersize cock was now also rock hard as he felt Michael's rougher hands rhythmically moving inside his lacy knickers. Sensations were sweeping over his body as he felt a delicious pressure building up, but he continued his own work on the man's comparatively huge penis. Michael was groaning in ecstasy as the fingers, tongue and soft lips were bringing him close to his own climax.
At last it happened. Little Ricky felt an ecstasy-inducing sensation as for the first time his spunk shot out into Michael's hand. Involuntarily his head jerked back, his lips releasing the man's cock just as it shot out a ribbon of fluid that landed on Ricky's mouth and cheeks. There was a cry from the other side of the room as Tania had her own orgasm to coincide with the others.
"Ohhh – good boy," she whispered.
Little Ricky smiled back. "Thanks, mummy," he replied, then licked the delicious white spunk from his soft, pink lips.