He loved dressing up in them whenever his roommates were gone and prancing around the house, acting like a sissy and pretending he was a girl.
Later in college, when he met Michelle, he was overjoyed to have made such a catch, despite her sometimes surly and bossy demeanor.
He kept his fetish a secret from her but one day, she came across his stash of women's clothing and she angrily confronted him with it. Michelle had used corporal punishment on Timmy several times previously and this time was no exception. Timmy quickly found himself over his stern girlfriend's lap getting his bare bottom paddled mercilessly as she scolded him for being a sissy.
Some time later, after she'd had a chance to cool down and think about it, Michelle reached a decision regarding Timmy's crossdressing. She said she'd allow him to indulge his desire to dress like a girl but the price would be his chastity. Initially, this started out with his small penis being locked up just a week, but as time went on, a week became two, and then three, until he found himself going a month between orgasms.
This was extremely difficult for the sissy to endure but he had little choice in the matter. Michelle kept the key to his chastity device at work and she only brought him home long enough to give him a quick, impersonal handjob before locking him back up again. And as time went by, these became even more infrequent until one day, Michelle informed him that after much deliberation, she'd thrown the key away.
"Sissies really shouldn't be playing with their pee-wees anyway," she told him indifferently.
"B-b-but what about the handjobs you were giving me?" he whined desperately.
"I really don't like having to touch that tiny thing," she said disdainfully, "And I think you'll do just fine without cumming from now on."
Timmy was devastated to think of what it would be like to be under permanent chastity but by now, he was too intimidated by Michelle to stand up to her.
Not long after that incident, Michelle began seeing other men, a fact she made no secret of.
"Since you can't satisfy me, it's only natural I'll have to find a real man that can," she informed him.
Within three months, she'd settled on a hunky diesel mechanic named Tom who was only too happy to keep Michelle sexually pleased. He moved in to their apartment and Michelle forced Timmy to take the adjoining room.
Being in a state of constant sexual frustration, Timmy was constantly horny but unable to satisfy his desires. Michelle took advantage of his pent up energy and kept him busy, making him service Tom every morning before he went to work.
It was all Timmy could do to fit Tom's massive erection into his mouth but with constant daily practice, he developed his own technique for deepthroating him and swallowing his seemingly endless loads of creamy semen.
Michelle found herself increasingly unwilling to deal with Timmy's personal needs and before long, she delegated the once a month job of milking the chastised sissy to Tom. In order to drain Timmy's balls of all his built up cum, it was necessary to massage his prostate gland for about half an hour. It wouldn't give him any kind of orgasm, but at least it would relieve some of the pressure built up in his blue balls. Tom went about the task with his usual good natured enthusiasm as Timmy assumed "the position" on his single bed.