The RoommateThis is pure fiction, and a cool fantasy. For the transvestites and crossdressers reading this story, please imagine yourself as the person telling it. After all, this really is your story.
Friday, March 9th:
It had been 3 weeks since I’d stepped foot in my apartment or had seen my girlfriend. I was really looking forward to getting back home after such a long business trip. As the cab dropped me off at my apartment, I began to feel that sense of familiarity that makes you relax. The sounds, the smells, the energy, missed by not forgotten.
I stepped into the elevator with my bags and pushed the fourth floor button. Damn the elevator was slow, but finally, it stops on four, and the doors finally open. I head out down the hall, toward my apartment door. I fumble with the key and put it in the deadbolt lock first. Oddly, it’s not locked. Diane must have forgotten the dead bolt again. I then put the key in the door lock, turn the handle and walk into the apartment. I look around, and something doesn’t seem quite right. There are some things missing, candles, plants, pictures. I panic as “burglar” flashes through my mind! But as I look around I see my TV, stereo, and the rest of my electronics are all there.
“Diane??” I call out. No answer. I look at the table in our kitchen nook and see what looks like keys on top of a note. As I approached, I recognized the keys as Diane’s. My heart sank as I opened the note. “OMG, is she dumping me?” I’m thinking to myself.
Well, dumping me is exactly what she did. I could hardly believe it. Diane dumped me in a letter of all things. Not even to my face. Diane was tired of the fact I was always away at work, and that I was too tired to do much when I was home. It turns out that while I was away, Diane met someone else, whom she so eloquently described as a real man, who doesn’t wear women’s clothing. A little salt thrown into the wound. And there I was, alone.
Saturday, May 18th:
I finish the Windsor knot on my tie, and put on my jacket. I’m getting ready to leave for Rick and Monica’s wedding. It sucks not having a date. I had RSVP’d for two, but by now, everyone knew Diane and I were splits-ville. At least I know a number of friends who will be going.
At the reception, I saw my friend Sarah. I hadn’t seen her in a few months. She came up and told me she was sorry to hear about Diane and me. Sarah and I had been good friends during college. We both majored in accounting, and ended up taking a lot of the same classes. Over time, we got to know one another, were in the same study groups and such. We kept in touch after school as well. She was working for a company in the Bay Area. I lived in the Bay Area as well, although I technically worked out the San Antonio office. It didn’t really matter too much where I lived versus my company office since I was on the road working with our clients 95% of the time.
At this time, Sarah and her roommate were not getting along. Sarah knew I had a 2 bedroom apartment asked if I was looking for a roommate. I hadn’t really given thought to sharing the apartment with anyone else. I could tell Sarah was in a pinch and well…let’s face…I didn’t really spend a lot of time there. It could help with rent too. Plus, it would be nice to have company while I was there. Mike is Sarah’s boyfriend. They have a serious relationship, but she doesn’t feel ready to move in with him. I’ve known Mike for a long time as well, and he knows Sarah and I are strictly friends, and is comfortable with the living arrangement. So I agree to let Sarah rent the other room from me month to month.
Friday, June 3rd:
I’ve just gotten back home from my latest business trip. Sarah and I yack about how each of our week’s went. Suddenly, Sarah gets a bright smile on her face. “By the way...” she says as she walks into her bedroom…”who do these belong to?” As she turns back, she is standing there, with an ear to ear grin, dangling my black pumps with 4 in stiletto heel from her fingers.
My heart sunk, and I think my face went completely white, followed up by 7 or 8 shades of embarrassment red. “Oh sh#t!” I think to myself, “totally busted!” I wanted to crawl into a hole. “Sarah,” I said, “let me explain.” Suddenly, the smile on Sarah’s face disappears.
“Wait a minute.” She said, “are these yours?” I closed my eyes. “OH MY GOD!” she exclaimed. I thought these belonged to some woman you brought home one night!"
Not only was I incredibly embarrassed, I was now feeling really stupid too. Thinking on my feet has never been my strength. Sarah had given me the perfect ‘out,’ but instead, I stuck my foot in it…pardon the pun.
“Yes.” I sighed, “They’re mine.” I couldn’t even look her in the eye.
Sarah looked at me square in the eyes and asked, “are you a crossdresser?”
I said, “I prefer the term transvestite.”
Sarah growled. “OMG...Oh, I cannot believe this!” “So…are you gay?”
“No.” I said.
“So, you’re bi?” Sarah questioned.
“No. I’m pretty sure I’m straight. Psychological studies indicate most transvestites are straight. Sarah looked back at me skeptically.
“How did this all start?” She gasped.
I walked toward the kitchen, opened the liquor cupboard, pulled down a bottle of gin, and a bottle of tonic. I looked back at Sarah and asked, “Drink?”
“Hell yes!” She fired back. One thing I knew about Sarah from our college days, she was good at asking questions of teachers. I knew she’d have a lot for me…
I told Sarah my life story as a transvestite. She was blown away. She told me she had no clue, and never would have suspected. I asked if she was angry or if she hated me. She told me of course not, but she was totally shocked and surprised. She asked if Diane knew, and of course she did. She asked if Diane broke up with me because of it. I filled her in. The conversation sort of ended awkwardly. We both departed to our bedrooms for the evening. Sarah would not mention this again for several months.
Friday, Oct. 23:
I get back from my business trip. It's already past dinner time, and I'm tired. I decide to take a shower and shave my legs. I know Sarah is out with Mike, and I'm looking for some dressup time alone. I take a few bites of leftovers when I hear Sarah come into the room.
"You're home early." I say as I turn...and suddenly stop. Sarah's eyes are red and swollen, and her eye makeup is smeared. She had obviously been crying. "What hapened?!" I exclaimed.
Sarah told me that Mike confessed to her that he slept with another woman. Sarah was devastated. I put my arms around her and gave her a hug. I got up and mixed a couple of martinis. Sarah downed her martini quite quickly, and then asked for another. I mixed and served her another, which she pounded quickly as well. She was on a path to getting really drunk and possibly quite sick. I asked her to stop at 2 drinks.
Sarah thought about it for a moment and then said, "OK." She then got up and went to her room. I heard some fumbling about and Sarah came back out with a joint. "Here, let's smoke this," she said. It had been a while since I had been stoned. Same for Sarah. As we smoked, the conversation would got rather silly. We began laughing and carrying on. This is what Sarah needed. As she was talking to me, I couldn't help but admire Sarah's legs. She had on a tight,red, knee length skirt, nude pantyhose and red pumps. Sarah noticed I was staring and asked, You like? Do you want to try on my shoes?"
I laughed, and said, "I would, but I don't think they would fit me."
Sarah grinned widely, got a crazy look in her eye again and she burst out, "I want to see you dressed up."
"Really?" I asked.
"Yessss....it will be so much fun!!" Sarah cackled.
And naturally, I agree to this.
We went to my closet and picked out a my gray skirt suit with white blouse, very sheer nude pantyhose and my black pumps. As I got dressed, Sarah asked if she could do my makeup and hair. I said, "sure."
It was a long process, but Sarah really did a nice job. I ended up looking quite convincing. The problem came during the makeup phase. I started to get very excited. My **** had become extremely hard and it was difficult to hide the buldge. I kept crossing my legs to hide it, but it was hopeless, I had a giant hard on and Sarah knew it. Precum had also been leaking and made a wet spot on skirt.
Sarah looked down at the buldge in my skirt and said, "I'm sorry. That's my fault."
I said, "No Sarah,. It's OK. You didn't know this would happen.
Sarah then said, "well, actually, I sort of did know."
We stared at each other, but didn't say anything for what seemed to be an eternity. Then, very slowly and deliberately, Sarah reached down and lifted up my skirt. I sat still. She then said, "Nice package. And no panties either."
With that Sarah reached down with her index and middle finger and stroked my hard **** in just the right place. I closed my eyes and leaned back. Sarah said, "just relax and let it happen...all over in your pantyhose."
And a few minutes later, I was moaning loudly and shooting ropes of *** into my nylons. Sarah leaned over and kissed me on the lips, and said, "this can't ever happen again between us..."