1. Nicole & Ted (Roommates Snow Saga)


    Date: 6/29/2024, Categories: Transgender & Crossdressers, Author: byWhyNotUs

    ... have to settle for watching the door. I began my ride and I was instantly moaning. Ted kept telling me to be quiet and tried to put his hand over my mouth.
    
    I wasn't sure if it was my sounds that gave us away, but a few minutes into our sex session, the door opened. Staring at us was Al, the current principal. Al and I were friends in High School and we had lost touch after graduation. We had said hello earlier in the gymnasium and he said he was happy for me. My eyes locked with his and I froze with Ted's dick buried to the hilt. I was embarrassed. Plus we were both so close to cumming, and I didn't know what to do.
    
    Al closed the door and said, "Don't stop on my account!" Then he stared directly at my boobs.
    
    "Really?" I asked.
    
    "You were making such enjoyable noises. I don't want to be the guy that denies an old buddy some pleasure," he said, "You're welcome to keep going, as long as I can enjoy the show, of course!"
    
    "In that case since I can see what you're looking at, I'll give you an even better show." I said.
    
    I pulled the shoulder straps off my dress and lowered the top, exposing my lacy pink bra. I reached behind myself and unclasped it. I balled it up and threw it to Al. He caught it and gazed at my humungous tits!
    
    "Ahhh, that's much better," I said. "Ready to watch?"
    
    "Oh yeah!" Al said.
    
    I lifted up and slammed back down on Ted's dick. I rode him hard as my boobs flopped around. I was focused on my orgasm but when I looked up I could see Al's ...
    ... jaw drop. Ted began to fondle my nipples and I saw Al whip out his dick to jerk off. My old friend was getting off watching me get fucked. The three of us definitely had the best time of anyone at the reunion! When we were done I stealthily put my plug back in. I don't know if Al saw, but he didn't say anything.
    
    "Hey Nick...shit, I mean Nicole, did you have a chance to see Tara tonight? You know we got married after college, right? Al asked me.
    
    "No, but if I see her should I neglect to mention what just happened in here?" I asked, trying to play it cool.
    
    "Actually you should. We're a bit of voyeurs ourselves and we are always looking for a new couple to fool around with. I would love to suck on those big juicy melons while I fuck you! With your permission, of course, Ted." He said.
    
    "That could be interesting," Ted said.
    
    "And of course you could play with Tara," Al said to Ted.
    
    "We're getting married in a couple weeks, so maybe after the honeymoon," Ted said.
    
    "Do I get a say in this?" I asked, jokingly.
    
    "NO!" They said together while giggling.
    
    "Well I would have said 'Yes'! My vision was a little blurry from the amazing pleasure my fiancée was giving me, but I caught a good enough glimpse of what you're packing!" I said to Al.
    
    The guys exchanged numbers and Ted promised to be in touch. We found Jen and Ben and they were ready to leave too. We didn't tell them about our escapade in Al's office or the offer he made us. It felt nice to keep a secret ...