Panty Wearing Caller
I had a lovely caller named “Nick” the other night. His story is much like many of you- he has a vast and creative sexual imagination, which led him to do things he was hiding from his girlfriend. What sort of things? Well, for starters, Nick was wearing panties as often as possible. He had quite a little stash of panties and kept them well hidden from his girlfriend.
His sexual imagination also led him to play with sex toys. Not the type of toys you would expect a man to play with, but instead, he played with dildos and vibrators. Nick would often take it in the ass with his own personal dildo when his girlfriend was away from home. Of course, he kept his panties on, just pushed to the side for easy access to his pussy.
Alas, all this was just part of what Nick dreamed a relationship could be like. In his sexual imagination, he saw his girlfriend with a strap-on, pegging him while he wore his pretty panties. He imagined she would become more dominant over time, perhaps even put him in chastity and take a lover for herself.
The Tables are Turned
What Nick didn’t know is that his girlfriend has a sexual imagination of her own. She dreamed of a real cock, not the little stub that Nick had. She wanted a substantial piece of man meat. It had been so long since she had really good sex she was getting frustrated. Then one night, it happened.
The little vibrator she kept at hand to give herself orgasms ( since Nick didn’t do it very well) was in her hand, and she was feeling so good she rolled towards Nick and put her hand on his dicklette. “I know what would be fun!” she exclaimed. She proceeded to convince Nick he should let her tease his dick and balls with the vibrator.
What she didn’t realize was that this was something straight out of Nick’s creative sexual imagination! As she played around teasing Nick, she kept edging her hand towards his tight little hole, nudging at it with the tip of the vibrator. Nick was in heaven. He couldn’t believe what she seemed to be doing. 
Nick spread his legs apart just a little further, subconsciously giving her permission to enter. She took the hint and nudged the tip of the vibrator into his tight little hole, making his peen drip pre-cum almost instantly. She drizzled some saliva on the vibrator studying it closely. She pushed it deeper, almost all of the six inches going inside Nick.
Almost instantly, he felt it start to wash over him, without even touching his dick. He knew he was going to cum, and cum hard, as soon as he felt the sensations that vibrator was making inside him. His girlfriend watched in fascination as he exploded, trembling and quaking with wave after wave of pleasure.
No Going Back From Here
A line had been crossed, and he knew there would be no going back. His girlfriend was so delighted with his reaction. She started planning out loud the next thing she was going to try. It didn’t take any effort at all for him to be convinced she would look great with a strap-on harness flush against her skin with a nice big dildo attached to it.
What she didn’t disclose at the time was the fact that she had found his stash of panties. Soon after she brought the strap-on home, she told him to go put on a pair of panties. He was shocked that she was taking it so well, but he hurried to comply. She left the panties on during their pegging session, fucking him while he was on his hands and knees. Again, he came without touching himself.
She knew she deserved better than what she was getting at home, so she told Nick she was taking a lover. She really did not give Nick any choice because if he didn’t comply, she would withhold this latest delight, and he would go back to the way things had been.
A Third Party Joins In
At first, she would go to Steve’s apartment, hooking up in his bed after a night out. But she eventually decided that Nick needed to see what a real man looked like, and so one night she brought Steve home. Nick was a little sad, but he knew he had to share, or he’d end up with nothing except his sexual imagination.
Soon, Steve was a regular fixture at their place. He would stay whole weekends sometimes, leaving Nick to sleep on the couch. But Nick didn’t care, because everything he had imagined was coming true! He was being turned into a cream pie eating dildo fucking sissy. The cherry on top of his sexual imagination sundae was the chastity device his girlfriend brought home one night. Nick wanted to be locked up so badly; he had told her his secret desire for chastity.
What Nick hadn’t bargained on was the fact that to earn his device, he had to make Steve hard by sucking on his huge cock. He had thought she would lead him down that path, but months had gone by, and she never suggested it, until now. Nick couldn’t show how eager he was to wrap his lips around that cock, but he wanted to so badly.
If you think things went smoothly from that point on, you are mistaken. Something ridiculous happened that had both Steve and the girlfriend laughing at Nick so hard he almost cried. Want to guess what it was? I’ll give you a hint- when he started sucking Steve’s cock, something happened that prevented him from being locked up.
Nick got hard as a rock from sucking Steve’s cock. He stayed hard after he was done. Even the laughter didn’t bring him down. They couldn’t fit the chastity device over Nick’s hard peen, small as it was. They knew the only way it would return to its normal state was for Nick to orgasm. Since there was a hard cock handy, that is just what happened! Nick was fucked by Steve. He shot his load and got locked up.
Do you wish the things in your sexual imagination would come true as it did for Nick? Do you ever have the opportunity to put your imaginings into words? I’d love to listen to your fantasies and help you act them out. Who knows, maybe someday your wishes will come true, and you will find that person who fits your kink perfectly. If not, you’ll always have me to play with!
Talk to you soon-
Nick had a girlfriend whereas i do not i am openly in panties and crossdresser in certain places i don’t crossdress at my current church or go anywhere i am known as a man. I used to have a complete life going out crossdressed Church stores condo. Some people knew me both ways. I have since hidden the woman side away and became an internet sissy I have tried calling you but have problems with the forms.
April Nicole, what forms do you have trouble with? Let me know and I will see what I can do to fix that issue for you!
What a wonderful story and what a wonderful girlfriend!! i think more often than not, these kinds of transformations take years to come to fruition, if they ever do. i’m certain it must often be a shock to a wife or girlfriend that their significant other wants a thick cock down his throat after years of pretending that he is a “man”. For those out there who have found this perfect situation, watching his wife or girlfriend get pounded by a real man while he sits quietly watch, bravo!! And like you say Mistress Stephanie, we have you to direct and guide us, and that is perfect by me! Sissy (Tiny) Timmy
I think a situation like this is rare indeed! I’m having fun guiding you, Tiny Timmy! Thanks for reading!
Hi Ms Stephanie: It sounds like Nick and his girlfriend are the ideal couple! Triple?
My goodness it all seems to start with those panties doesn’t it? Cannot blame Nick for that, I’ve had more frillies than boxers, for years. How can you not want to start your day stepping into that epitome of femininity?
Of course, next to follow, the desire to play in the back yard with a slew of toys cannot be resisted…(only a matter of time). Finally, this is too much fun not to call a friend over to share in the fun!
Sounds as if this journey is going precisely as planned, fulfilling the wishes of all parties.
Have fun, stay pantied, caged and most of all, safe!
little davey- it all did seem to work out in everyone’s favor once the ball started rolling! Wouldn’t it be wonderful if more people could have that experience? Thanks for stopping by!