Archive for the ‘Cross Dressing Phone Sex’ Category

Crossdressing Boyfriend Phone Sex

Catching my boyfriend crossdressing made me so wet, I couldn’t help but squirt hard on his cock.  My boyfriend was staying over at my apartment the other night. I told him I’d be out for a few hours, but came home much earlier than expected. As I walked into the apartment, I didn’t see him, […]

Panty Boy Lingerie Shopping

I decided to take one of my favorite panty boys out shopping for some lingerie. Once at the lingerie store, we made our way to the dressing room. Several female employees were eager and willing to assist him in finding the perfect lingerie. The employees picked out a sexy red set with some white thigh-high tights. […]

Forced Bi Sissy Cumslut

A sissy cumslut can’t resist some sexy new lingerie, even if that means giving a forced bi blowjob. A male friend and I decided to spice things up by inviting over a sissy I played with recently. When the sissy arrived, my friend presented the sissy with a silky soft set of lingerie. As the […]

Panty Boy Phone Sex

I love playing with panty boys, especially while they’re wearing my panties. I was playing with someone the other night and we started talking about my panties. He hadn’t worn any in years and wanted to try again, but didn’t have any of his own. Smiling, I told him to strip off his clothes as […]

Sexy Cross Dressing Date

I had the best cross dress date with one of my favorites, Silky. It’s always a hot time when we link up to play. We always get dolled up. She loves when I have her dress up for me. I get all dolled up with her because a lady always has to look good! I […]

Coerced MtF Transition

It was about time I led another friend down the path to womanhood through a coerced transition.  A close friend recently revealed to me his penchant for crossdressing, though he hadn’t told many others out of embarrassment. I thanked my friend for his openness and encouraged him to take things more public. I bought him […]

Sissy Cuckold Phone Sex

I made my sissy cuckold husband watch me get fucked hard and lick up another man’s creampie. My husband arrived home early from work. He called out for me then wandered around the house when he didn’t hear back. As he approached the room, he could hear me moan, telling someone their cock was much […]

Lacie’s Lingerie Phone Sex

A few days ago, Lovely Lacie had stopped into the chatroom for a bit. I’d just gotten her a new set of lacey black lingerie; a sexy black pushup bra, black lace panties, and some thigh-high tights. After a bit of teasing, I slipped the panties over her clitty and rolled up the thigh-high tights, […]

Cross Dressing Phone Sex

Crossdressing phone sex at the bunny ranch. One of the sissies who calls me sets up a fantasy about the ranch in Nevada. One of the sexy bunnies specializes in cross-dressing. We got a suite at a top-notch hotel and the room has a vanity that will make any girl’s panties cream. I made the […]

Forced Bi Sissy Blowjob

A concerned wife asked me what she should do about her husband’s crossdressing; I decided it was the perfect opportunity for her sissy husband to give a forced bi blowjob. A friend of mine reached out to me. She was concerned about her husband; she had recently caught him crossdressing and wasn’t sure what to […]