[Note: In this story Timmy undergoes late-onset puberty at the age of 18.]
Ever since he was a teen, Timmy had been acutely aware of his prominent bottom. He’d always been a soft boy, covered with baby fat. His belly was soft and his chest was just two small conical breasts peaked with rosy pink nipples. He tried to diet and work out but nothing seemed to help.
After puberty, certain types of sly women began to find his bottom very interesting. At first they would just find excuses to pat and rub it. This gave young Timmy strange feelings. Later, when he was alone he would remember these incidents and feelings and he’d secretly play with himself. He always felt very ashamed after he played with himself but he couldn’t help it. When he played with himself he would have vague fantasies about those women doing other things to his bottom: strange, invasive, humiliating things. And it wasn’t long before women actually did begin doing these things.
The first woman to do these things was his own mother. Soon after puberty she would continually find excuses for doing things to his bottom, such as taking a rectal temp, giving enemas and finally, just “exercising” it by thrusting her finger in and out of his well lubed hole.
One day his mother told him she was going to take him to a lady doctor that specialized in boy’s bottoms. His mother had spoken to Jimmy’s mom and she had recommended the doctor. (Jimmy was a boy that lived down the street and who also had a large bottom.)
After arriving at the lady doctor’s he soon found himself in the usual position, naked from the waist down and bent over a table. His mother stayed in the exam room to watch of course. After the usual poking, prodding and finger fucking the lady doctor discussed his mother’s current bottom treatment regimen and complimented her on her “exercise” program. Then she volunteered to demonstrate an even more effective method of “exercise”. Timmy was shocked to see the lady doctor slip off her skirt and strap-on a dildo over her panties. His mother watched with excited interest as the lady doctor moved behind Timmy, gently penetrated him and then proceeded to slowly fuck his tight little hole while he squirmed and gasped.
“You’ll probably notice a very perceptible rising in his male member when you do this,” said the lady doctor. She was right, Timmy’s peepee was very red and stiffly erect. “This is perfectly normal and is a sign of good health. Although this may be a good time to discuss Timmy’s masturbation habits. How often does he masturbate?”
“Oh, about twice a day,” said his mom.
“Mom!” objected Timmy.
“Shhhhh, Timmy, grown-ups are talking,” said his mom.
“When I examined his prostate earlier,” said the lady doctor as she continued to fuck him, “it seemed unusually swollen. I believe the ejaculations he achieves through masturbation aren’t fully effective. You should see the benefit of exercising him in this fashion in a minute or two, however.”
She was right, after another minute of being steadily butt-fucked he gasped and tensed and jet after copious jet of cum began spurting out.
When he finally stopped spurting and collapsed on the table the lady doctor eased the dildo out of his aching, throbbing hole and said, “I think you’ll find that after a release like that the swelling in his prostate will be completely gone.”
“Where can I buy one of those!” asked his mom. Timmy just groaned.
“You can buy one from my receptionist on the way out,” replied the lady doctor with a smirk.
A similar scenario was played out in junior high school when Timmy began having spontaneous erections in biology class. The lady biology teacher sent him to the school nurse, the nurse checked with his mother and soon Timmy was bent over a table being sodomized with a strap-on worn by the school nurse. From then on whenever he got a spontaneous erection in biology class he was sent down to the nurse’s office for another session with her strap-on.
When Timmy became a little older he interviewed for a job as an office boy. He was interviewed by a very confident young women in a business skirt-suit. As he was standing outside the interview room waiting to go in he noticed two other business women eyeing his conspicuous bottom. He heard one of them whisper to the other, “Ummm, he’s got a nice one,” and they both laughed softly. He couldn’t help but notice that most of the other men he saw in the hallways also had large, soft bottoms. They were all shy and avoided making eye contact.
The interviewer told him that he was definitely what they were looking for. All he had to do before he was hired was submit to a special physical by the company’s nurse practitioner. Timmy groaned inwardly – he had a pretty good idea what this would entail.
Once in the nurse practitioner’s exam room she pulled on a pair of latex gloves and told him to lower his pants and underpants and bend over her exam table. She lost no time in touching and caressing his big soft naked bottom. Then she gently spread his cheeks apart and inspected in between. She told him she was going to test his rectal responses but first she would have to fit a special cuff over his penis. After she put the cuff on she proceeded to lube up his hole and to poke, prod and fuck him with her fingers and various long, thin, vibrating instruments until his stiff throbbing penis exploded into the cuff filling the attached reservoir to the bursting point. Timmy made quite a shameful spectacle, panting, gasping and moaning throughout. The nurse smiled smugly as she eased the slimy cuff off his slick, slippery cock. “I think you’ve proved yourself adequately responsive,” she said with a smirk. (“Why are they always smirking??” thought Timmy.)
After he was hired, the various lady execs in the company took turns taking him into their offices and sodomizing him with their strap-ons until his semen jetted out onto their desks, chairs and carpets.
Then one day one of the lady execs took him into her office and he immediately pulled down his pants and underpants and bent over the desk without being told. She laughed and came over to rub his big, soft bottom. “You’re got such a lovely big bottom,” she said, “in fact, it’s a perfect bottom for a eunuch. I’m very fond of eunuchs, as it happens, and I especially enjoy making new ones. Let’s see what we have here,” and she casually ran her hand up, under and between his legs. She stopped to gently grasp and caress his tight, full sac. “Hmmm, I can see you’re not a eunuch yet but we can fix that,” she chuckled. As soon as she said that Timmy gave a loud grunt and spontaneously spurted a huge load all over the side of her desk. “Hmmm, I see you like the idea,” she purred. “All the other office boys that work here have been made into eunuchs,” she said with a smile. “I love having lots of castrated males around me at work.”