Chis(topher) & Chris(tina)

by djfmonkey

23 Nov 2021 1763 readers Score 9.7 (114 votes) PDF Mobi ePub Txt


Well Chris and I were enjoying life, I got to meet her overly accepting parents, they accepted me with open arms, making me feel slightly uneasy as I knew Chris wouldn’t be accepted as well by my parents, I do plan on introducing them in person at some time, meanwhile they know I’m living with her, and that she’s a he as well. Whenever we talk about Chris, they get uncomfortable and try to change the subject. One phone call home my mom told me that my grandparents were planning a trip to the city, and they said they really wanted to spend some time with me, and asked if I could manage to do so without revealing my sexuality to them since they still didn’t know, my mom said she tried to discourage the visit but they insisted, they were staying at the Marriott in 2 weeks coming in on a Friday and so as not to upset my work schedule. They asked If I could show them around the city on Saturday. I dreaded telling Chris about this, and discussed him staying as Chris-topher for the day, or intriguingly maybe as Chris-tina, Chris said we’ll it’s time I meet some of your family whether as your girlfriend or just a male friend. I was shocked by his willingness, I thought it would upset him. But Chris being Chris and all I’ve come to love about him.

Friday night came and gramps called and said they arrived that morning and hoping we could get together tomorrow still, I said sure, but didn’t say that Chris was coming yet, as we still hadn’t decided which way it would be as him or her, I became increasingly nervous. Anyway Chris had to go into the office for a few hours on Saturday morning for a brief staff meeting. My grandparents weren’t scheduled to show at our apartment till about 10. Chris informed me he would meet my grandparents as Tina, and we’d be boy and girlfriend as we shared the apartment and would fit their mindset better than Topher. Chris thought he’d be back before 9:30 possibly cutting it close, so off he went.

At 9:30 gram and gramps showed up at the door, early, nervously I began to show them around the big place, beautifully furnished, and views. Gramps said man the cost of this place must be absolutely asinine. How ever do you afford this all? you’ve got to be doing very well for yourself, we’re so proud of you, with that Christopher opened the door and came in, my Jaw dropped as did his, as I hoped I could have taken them down to the coffee shop while Chris changed and joined us after. But he’s already in the door and I said um…. This is a friend of mine Chris. They politely said hi from afar and Chris ducked into the bedroom quickly. Scared, I now wasn’t sure which Chris was coming out of that room, I continued to talk to the grandparents, shortly after, Christina came out, in that beautiful red dress we had our first date with, she graced into the living room and introduced herself as Christina, and I proceeded to introduce my grandparents to her, my grandmother gave me the quiet side eye, as I think she might have put 2 and 2 together. But my dirty old redneck grandfather true to form, didn’t notice anything but that cute red ass in that nice red dress, as he did a quick slap grab ass on Chris, who ever so politely muttered “oh you dirty boy you” as grandma slapped him. Oh my god! I thought, my grandpa just ass grabbed my boyfriend I thought to myself. Chris knew what he was up against and being the person she is, took it with a grain of salt, not only humoring him but encouraging it ever so slightly, flirting-ly. Later grandpa took me aside and said “she has the nicest ass he’s probably ever seen, and not to worry that her breasts are pretty small, because he’s found smaller breasts the better”, “you see they won’t droop as she gets older, and she stays nice and tight”, I just closed my eyes and shook my head. If only Chris knew what he just told me.

We first went up to Times Square and proceeded to Central Park where we took it slow as there was a lot of walking, we decided to stop and sit for lunch, and Chris sat right next to grandpa purposely, as I gave her the look “please don’t start anything “ she complimented him admiringly, talking about his small town hardware store he ran for 50 years. He looked across the table at me and gave me a wink and thumbs up, saying I sure got a good catch here, and I’d better hang onto her. Christ I thought, he’s ogling a guy in drag, if only he knew, meanwhile grandma was very quiet except to try to put grandpa in his place, which with Chris flirting was difficult to say the least. We went to several other sights and finished with dinner and a play. Grandma pulled me aside at one point and asked if I new what I was doing here, I assured grandma I loved her very much, but yes indeed I love Christina too, with all my heart, we were made for each other, she slightly smiled and said ok then. So grandma wasn’t being fooled for one minute. But grandpa didn’t even remember that earlier Chris the male or why he was even in our apartment earlier, where Tina came out of the Same room that Topher went into. Was he that naïve? I thought.

Afterwards Chris and I dropped them off at the hotel, and proceeded to Clancy’s bar, and discussed the day, often laughing at the situations and innuendos that we took, or I should say, Chris took, Chris was a defiantly a bold person today. We went back to the apartment and proceeded to have another great sexual session. Making out with Chris in that sexy red dress was great, getting her out of it was even better. The sex was fantastic, he blew me and I him till we both came and shared the double shot of cum with each other in a kiss, swallowing each other’s mixture in delight. I fucked him and came again trying to pull out to get to his mouth and missed as I got my first spurts on the red dress next to his head. Our sex life that night took on a new meaning by Chris repeatedly bringing up grandpa, as we laughed, and kept asking what would he think if he saw us now. Heart attack? Explode? Don’t know, can’t imagine, “stop talking grandpa when your in me” I proclaimed, Chris responded by signing to me the Frank Sinatra tune “I get a kick out of you” only he kept changing the words to “I put my dick in and out of you”, saying grandpa would like that song wouldn’t he? Yeah right, I wonder if grandma ever told him……

by djfmonkey

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