Feminization Fantasy Phone Sex: Alvin in Wonderland

For as long as I’ve known Alvin, he’s always had a thing for me. Staring at me, blushing, smiling and stuttering, always complimenting my outfits. Even my jewelry and shoes. He was shy and delicate looking and more pretty than handsome. Even before we began feminization fantasy phone sex, he had feminine features. I like rugged guys but Alvin was sweet so I asked him to a Halloween party. He was excited to go of course but when I mentioned that we could pick out costumes together he got really excited. And blushed a lot.

feminization fantasy phone sex

When I made a few costume suggestions I noticed that he got excited with the ideas that involved him dressing as a girl. If he had a phone sex feminization fantasy, then I wanted to see how far it went. How far he would go. As a girl. I couldn’t believe my luck, our first date and it was going to be a femme fetish role-play. How lucky am I!

I picked out a sexy white rabbit costume for myself. It consisted of a white barely there bikini, some fur cuffs and boots and a cute little fluffy tail. Big ears and some sexy makeup that made my skin look pearlescent white. I found a very daring short blue dress with thigh highs, heels, wig and makeup. He looked like the perfect slut, ready to chase my little white rabbit tail down any rabbit hole I wanted him to go. *snickers* I told him as we headed to a big party that for the night “he” would be my girlfriend Allie. 

Allie made a hot girl actually. Certainly hot enough no one would ever guess she was a dude living out a feminization phone sex fantasy.

He was petite and pretty enough that with the wig and makeup, he looked like a she. A pretty hot girl actually. Certainly hot enough no one would ever guess she was a dude living out a feminization phone sex fantasy. We partied, we drank, we smoked, we danced to sexy music. Allie was having a lot of fun being my “girl friend” that I pulled her into a bedroom and pushed her on the bed as I laid next to her and we started making out.

I reached between her legs and rubbed the hard “clitty” through her panties. One of my guy friends slipped in the room and came over to watch us. Allie was drunk and high enough that “she” was all for it. I told my friend to lay down next to us and just join in when I gave him the signal. He could kiss and pet until then. 

I lay facing Allie and rubbed against her, sliding my hand down the front of her panties and playing with her clit. Under her skirt only I could see what was really there. Allie started to squeak and try to cover up so my friend wouldn’t see anything. I just kissed her and told her to hush. My friend was kissing Allies neck and reaching over her to squeeze my tits. I pushed our panties to the side and rubbed Allies clit against mine. Hers was bigger. *wink*

I placed his cock against Allie’s “pussy” and told him to push.

I pushed it inside my tight pussy and then reached over her to grab my friends cock. I told him I would guide him inside my girlfriend. I placed his cock against Allie’s “pussy” and told him to push. He moaned and gasped as he entered Allie’s super tight pussy. Allie squealed and clenched and thrust against my pussy. 

My friend and I were both pressed so tight against Allie that she couldn’t move. I kissed her and whispered she was the perfect girlfriend to have a threesome with. She giggled too but my guy friend missed the joke. He didn’t care, He was enjoying fucking Allie’s super tight pussy so much that he didn’t pay attention to anything else. We all fucked like that until we came, all three of us together. 

I told my guy friend to go after he was done. Allie shuddered and thrust in my again when my friend pulled his cock out of her pussy. Allie never pulled out of my pussy, she just stayed hard, even after cumming, and kept fucking me. I told her that I’d dress her up and take her out for secret three ways anytime she wanted. I said I loved her feminization fantasy phone sex desires and wanted to help her get off with her fetish. When we got back to my place after the party and Allie took off her wig, Alvin stood there in his dress and fell to his knees, kissing my feet, thanking me. Now we play dress up on a regular basis. And only he and I know the truth.