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After several days wearing it, I made a timid attempt to withdraw my cock from the device – and found that the urethral catheter was totally effective in making the device escape-proof; there was no way I could withdraw my penis far back enough so that it cleared the insert. I realized that once Mandy had custody of both keys, I would for the first time experience totally secure enforced chastity. The thought made my stomach flutter in apprehensive delight.I also discovered that the urethral insert was also an effective deterrent against any attempts to furtively masturbate; endeavouring to do so resulted in the insert chaffing inside my urethra, which was a most unpleasant sensation. Several men posting on online chastity forums also warned that trying to jerk off when wearing such devices risked irritation, possible internal tissue damage and infection – which were definite reasons to refrain from the attempt in addition to the uncomfortable chaffing it caused.After two weeks. He tried his luck with women, but a broke, effeminate looking guydoes not get much female attention.When he reached thirty the urge to crossdress resurged. The little sparecash he had was spent on sexy underwear, shoes, dresses and makeup.In his mid thirties he decided to create a profile on a contact site, inthe name of Debbie36. He was amazed at the attention he got. Guys weremessaging him all the time. The massages ranged from polite to obscene.He had fantasies about being a woman and having sex with a man, but neverthought it could actually happen. He met a few of the polite soundingmen. Always the meetings ended with him using his hands and mouth toplease the men. It seemed a fair exchange for the attention they gavehim.Most of the men wanted to fuck him. He was always getting asked to dothis, and he started to come around to the idea. He practiced on himselfwith various objects until he was comfortable. It did not turn him on toomuch, but he knew it would make him even more.
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