Crossdresser’s First Anal Orgasm

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A young man still experimenting with his body, found a new fetish he enjoyed quite a lot. He found the joys of anal masturbation. He had heard rumours of an orgasm so wonderful it would leave you shaking afterwards. He was in search of his very first prostate orgasm. This is the story of the first time this young man would discover the joys of prostate pleasure.


Our story is set during an Autumn day, early November, with our young man we will call Zack. Zack was 20 years old, slightly tanned skin, dirty blond, green eyes and has discovered a handful of fetishes he enjoyed quite a bit. His most recent venture was anal play and prostate pleasure. Zack had experimented over the past year with various toys and methods to reach this mythical prostate orgasm everyone was talking so much about. He had heard that being in chastity for a week prior to the act would increase the chances of having such an orgasm. So he went online and found a nice pink chastity cage. After about a week he finally had his key to the orgasm he most wanted.

So, Zack donned his new cage and ventured on his journey. He hid the key in a public room of his house to deter him from trying to unlock himself, as his parents would be suspicious of what he was doing. Throughout the week he teased himself with porn and anal play, but was very careful not to play with his penis as he was sure it would ruin the experiment. He grew increasingly horny and his balls seemed to ache with not being allowed to release. On Thursday, one day almanbahis şikayet prior to the full week, he went through his routine of teasing his prostate hoping that on Friday he would be able to have a full on prostate orgasm.

Zack had another fetish; he enjoyed cross dressing. He would steal his sister’s clothes sometimes and dress up and look in the mirror at his girlish curves and tanned skin. Today, he wanted to wear a tight, short, black dress while teasing his ass. He heard that the more you get into the act the more likely you are to succeed. He also found a nice black thong to match his dress. After prepping for his session of teasing and pleasure, he took one last look in the mirror to admire himself. He looked so much better dressed as a girl than a guy. He wondered to himself why he didn’t go out in public dressed like this and find a real man, instead of using a fake silicone dildo. But that wasn’t important right now. He was so turned on by how he was dressed and how horny he was, that he couldn’t wait any longer.

Zack started by attaching his dildo to the wall and giving it a blow job like he was milking a real cock. He get so into the sucking and licking he almost forgot what he was trying to do. Zack pulled his down off his chest, revealing a nice pair of breasts. His body has this habit of storing fat in his breast area, so he has breasts somewhat resembling real boobs. He teased his nipples till he couldn’t stand it anymore, he was so horny at this point he just wanted the dildo in his almanbahis canlı casino ass.

He took the dildo off the wall and lays down on his side. The spooning position was the position Zack found to put the right amount of pressure on his prostate. He lubed his dildo and his ass up and slowly started to slide it inside. He was used to anal play, so it went in rather easily. As soon as the dildo entered his girlish hole, he felt a slight pain, but instant pleasure as well. It usually took him a minute or two to find his prostate, but this time it was very easy to locate; it seems the chastity cage is doing its job. As his hole loosened up he started to speed up his strokes. He felt the pleasure getting stronger and stronger as the dildo rubbed his prostate more and more. This was unlike any prostate pleasure he had felt before. He was certain he was very close to what he was yearning for. He wanted this orgasm so badly.

As the pleasure began to grow increasingly stronger and stronger, his strokes got faster and faster, and stronger and deeper. The feeling was similar to needing to urinate, but he had heard this is exactly the feeling he was looking for. He kept going as the pleasure kept building, keeping relaxed so to not ruin the sensations. Seconds went by that felt like minutes as the pleasure kept building and building, and as he reached the peak of pleasure, his body tingled and his mind went numb as he felt his prostate shoot a stream of liquid out of his cock hitting his leg. He was shocked! He almanbahis casino didn’t expect to ejaculate from a prostate massage. The orgasm was incredible as he kept massaging his prostate. He thought he would feel the feeling after a normal orgasm of guilt, but he was still as horny as he was before, if not more. And as he rode the previous while still pounding his hole he felt the pleasure in his prostate growing again. This was incredible! As he reached the edge again, he shot another hot stream of liquid from his cock…his body tingling with every thrust of the dildo. As he rode out another prostate orgasm, he felt the pleasure slowly fading from his body. He figured the fun had ended and was about to finish up…As he was going through a couple more slow deep thrusts to finish his session up, he felt that pleasure that was fading returning ever so slowly. And as he picked up his pace the pleasure built even faster than before as his prostate released even more liquid from his penis. At this point Zack was moaning with pleasure and panting like a girl. He had had three of the most amazing prostate orgasms that he had only dreamed about.

As his limp and totally sated body lay on the floor, the dildo slowly slipped out and he lay there for a second basking in the afterglow of his milking session. He couldn’t believe what he had just experienced. He got everything he wanted and hoped for, if not more. Zack cleaned himself up, took off his clothing and hopped in the shower. He could barely stand long enough to wash himself off, but managed to wash up. He then collapsed on his bed and took a very well deserved nap. He fell asleep to the experience he just had, and thought to himself, he may never need to take this chastity cage off if these are the kinds of orgasms he can have.

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