My Sissy Boyfriend (Closed)

[newgirl1980]

Closed for SexyVita

I had been looking forward to today, Friday, for the better part of two weeks. My girlfriend was leaving straight from work to visit her mother for the weekend, and I had told her that I had too much work to do to join her. I work in an office, an accountant, but it is just as easy for me to work from home using the VPN, so I had told Melissa, my boss, that it would be easier for me to work on month end closing from home where it is quiet and there would be little distraction, and she could reach me there by phone or email if need be. The other reason it would be easier for me to work from home is that I can be much more comfortable, that is, I could dress much more comfortably. I hate men’s clothing – it is unimaginative, frumpy-looking.

I lived by myself for a long time, and had amassed quite a collection of ladies’ clothing, enough so that I once went over ninety days without wearing the same outfit twice. When I met my girlfriend, I was torn with what to do, and ended up sacrificing my entire wardrobe to Goodwill in order to begin a more normal lifestyle. After two years, though, I realized I had given up my true self, and started to explore my girlfriend’s closet. So I have secretly, for the past year, played in my girlfriend’s clothes, often wearing her office clothes from the day before so as not to dirty or crease her clean clothes. Thus, being the end of the week, I had a wide selection to choose from.

I looked at myself in the mirror in the bathroom, having stuffed my girlfriend’s bra with two pairs of her pantyhose, the third pair disappointingly failing to cover the hair on my legs. They would look so shapely, I thought, if my girlfriend would only own some high heels, but she was more the practical type, and I settled for wearing her plain black flats. I rubbed my “breasts” through the fabric of her white silk shawl collar blouse, my hands snaking underneath her black suit jacket. I looked down, admiring the matching suit skirt dancing at the tops of my knees, and then at my girlfriend’s cosmetics, lined up on the vanity for me to use. Before that, however, I stood to retrieve her jewelry box and the one item I had repurchased for myself, my long wavy brunette wig.

 

[SexyVita]

I’d planned to leave straight from the office to visit my mother for a few days. But a five o’clock call from Bud, my boss, had put an end to my weekend plans. “Collette, I know this is last minute and all, but Midwest Electronics is sending some reps out on Saturday and I need you to show them around. I’d do it myself, but the family has plans this weekend.”

I sighed. “Yeah, sure. I’ll take care of it.” Bud was married with four kids and I knew he hated disappointing them. Still, the fact that I had to cancel my plans so he didn’t have to just pissed me off. But, Midwest Electronics was one of our biggest customers and it never hurt to be hospitable to the clients. I mean, I like my job and my boss but sometimes Bud can be a bit insensitive to anyone that is not one of his four daughters. I called my mother, who was disappointed that I wouldn’t be able to come. I told her we would just reschedule for the following weekend, which seemed to mollify her. Then I spent another two hours finishing my business for the day. Finally, I headed for home. The clients wouldn’t arrive until Saturday afternoon, so at least I had that much of a breather.

Weekends are normally the only time my boyfriend, Kris, and I have to spend together. I’m something of a workaholic, getting home late most nights, and after work hours, he likes to surf the web and Lord knows what else on that high-powered laptop of his. So we rarely spend much more than an hour a day together during the week and he’d seemed a little out-of-sorts when I told him about my trip to see my mother. So I decided that rather than call I would surprise him by just showing up at home. To preserve the surprise, I parked on the street rather than in the garage and quietly unlocked and opened the back door.

The house was quiet, the TV was off and Kris wasn’t on the computer in his office as I’d expected him to be, so I turned for the bedroom. The sight that greeted me left me momentarily speechless. Kris was standing there wearing one of my outfits! But more than that, he was wearing a wig, and jewelry. I was so shocked that I had no idea what to say, but my speechlessness didn’t last long.

“Kris, what the hell are you doing in my clothes!?”

 

[newgirl1980]

I was standing in the bedroom having just returned Collette’s jewelry box to her dresser when Collette’s voice startled me. “Kris, what the hell are you doing in my clothes!?”

I was shocked, and speechless, my mouth agape. “Uh, er, Collette! What are you doing here? I did not even hear you come in,” completely missing the point. “I mean …” Suddenly remembering I was standing in front of my girlfriend, in her clothes, my hands flung up, my arms crossing in front of my chest as if I were a naked schoolgirl hiding my bared breasts from an intruder. Collette’s grandmother’s pearl bracelet slid down my thin arm, and I reached with my off hand to pull it back up to the wrist, now clasping my hands in front of my chin, my elbows tight against my sides, my breasts squeezed together, straining the buttons of her blouse. The excitement and weeks of anticipation of this weekend quickly drained from me, and I now felt ridiculous and ashamed standing there dressed as a woman.

“I, uh, I don’t know what to say, Collette. But I will change out and wash them.” I reached up and pulled the wig off of my head, plopping it onto my dresser. “I thought you were going away for the weekend.” Turning back, I reclasped my hands, now in front of my crotch, looking even more pitifully like a guy in girl’s clothes. I looked down, afraid to make eye contact with Collette, and nervously lifted my left knee, the toe of her black leather flat pivoting on the floor as the hem of her black suit skirt slowly swayed around my knees.