Tiffany's First

Transcript: “Feels good doesn’t it?” Tim’s girlfriend Sasha cooed behind him. 

Tim could only barely mumble out a reply between his moans as his girlfriend simply looked on in amusement. Losing the bet had meant that his girlfriend could do whatever she wanted with him for twenty four hours. Of course, the fact that he had a witch for a girlfriend had certainly made things a lot more interesting. This wasn’t the first time that he had been turned into a girl, but it was his first time, albiet by a strap-on, and also the most pleasurable. This was undoubtedly turning into the best bet he had ever lost.

The sensations were incredible. Feeling ever inch of Sasha’s well lubricated strap-on sliding into his body’s virgin pussy, stimulating pleasure centers he never even knew existed before. He could feel the pleasure building, like a warm pressure in his nether regions. He squealed to Sasha to go harder and faster as he moved his hips rhythmically to meet her thrusts.

His girlfriend teased him as she watched him respond, “Like it now do we? Ooh, look at you, taking it like a pro. You know, I do believe that you’re a natural. Good thing too, since I already called Tommy over, you know his reputation don’t you?” 

Tim’s eyes widened visibly in an expression of shock, a strap-on was one thing but—

Sasha continued, “Of course you do. You didn’t really think that this strap-on was all we’d be up to now did you? This was just a warm up, for the real thing. I wanted to make sure you were all wet and ready for him. Tommy’s got a little fetish for threesomes you see and I owe him a favor, so tonight, Tommy’s going to get to have the two of us. The real trick though is on him, he doesn’t know who you really are! And as long as you moan and squeal like a little whore, he won’t ever know! So be a good little girl and act, if you need to, though I highly doubt it, like you enjoy it whilst he’s fucking your brains out, alright? Oh, and one more thing, we can’t be calling you Tim for awhile, now can we? How about Tiffany? I think the name suits you. So how about it Tiffany, are you ready to try the real thing?”