Roommates Adventures After the Snow
Date: 6/2/2024,
Categories:
Transgender & Crossdressers,
Author: byWhyNotUs
... anything," he said.
"She kinda brought it up, when I offered to do her a favor and it took off from there," I said.
"What favor?" He asked.
"I think you should talk to her," I said.
"Bullshit! No secrets, remember. I just made you cum three times and you're carrying a bunch of my baby batter inside you," he said.
"Don't be gross!" I said.
"I'm sorry, you know how I am by now. Would you Please tell me what she wants you to do," he said, emphasizing the word 'please'.
"Ok, long story short, she wants me to flirt with her ex-fiancée and fool around with him a bit. Then when he finds out I have a special clit, she'll jump out. It's a silly little prank. If you don't want me to do it, forget it," I said.
"Oh no, you have to do it! Screw that guy Ted that hurt our Jen. It will be hilarious. I'll tell her you can only do it if she can video his reaction, so we can enjoy it forever!" he said.
"It's a relief that you're okay with it," I said, "But do me a favor, when she brings it up, don't tell her that I told you."
"Come on Baby, you know I'm easy going," he said, "Now what about these dates. Do you want me to take you out to get some practice being out, or do you want me to take you out because you want to spend some time with me out of the house?"
"Both?" I questioned.
"That's all you had to say. Tomorrow night, I'll wine you, dine you, and then bring you home and make slow sweet love to you! How does that sound?" He asked.
"That sounds ...
... wonderful!" I said.
"Perfect, so why don't you make us dinner and then we can watch a movie," he said.
THE NEXT DAY
Jen picked me up and we went shopping. We bought not one, but three sexy mini dresses. They were all low cut and showed off a ton of my cleavage. They barely covered my ass and if I bent the wrong way, whoever was looking would get a nice flash of my panties.
Ben took me out on a few dates and I felt like I was the center of attention. I've heard of most women complaining about guys staring at them, but I loved it. Jen had taught me well and I didn't know why I was worried about being out in public at a nice restaurant. I started going out to lunch with her too and she decided I was ready to mess with her ex-fiancée.
EVENING WITH TED
After lunch with Jen, she took me to get my hair, fingernails, and toes done. She decided to go with the tiniest black dress we bought. It had spaghetti straps and clung tight to my body. She gave me a strapless bra that pushed my boobs up so high that she told me to be aware of nip slips. We dismissed the thong, because she wanted me to be tucked really well before my reveal. I had a sexy pair of black boyshorts that were perfect. The cupped my ass cheeks really well and made my butt look awesome in this dress.
Jen dropped me off at the bar Ted usually goes to on Thursdays. The stool next to him was empty and I sat down and ordered a Cosmo. It wasn't my favorite drink, but it was the girliest one I could think of. I ...