Beginnings of a sissy

I’m 35 years old and have been with my wonderful girlfriend, Becca, for five years now. I met her at her work, where I go to volunteer twice a week. It was pretty much love at first sight. When I first volunteered there, I also found out that an ex roommate of mine, Tiffany, from about 7 years past works there also. So did her then kid, now grown up sister, Nikki. It was an awkward reunion, considering the last time I had seen them, they both walked in on me, in Tiffanys room, dressed up in Tiffany’s bra and panties, pulling up one of her stockings up my thigh. Needless to say, that roommate agreement was at an end and I moved out.
Since my early teenage years, I always felt uncomfortable with myself in a young mans role. I am not one of the typical “girly man” types. I’ve always been taller and bigger than everyone I was around. All through school, I was asked to wrestle, play football and basketball. I never wanted to and instead would sit in the bleachers at practices and games and watch the cheerleaders, wondering why I couldn’t be one of them. Why did I have to go to church in a suit, instead of the cute dresses and skirts the girls my age were wearing? Why did guys always have to be tough? (Now I’m 6 ft. 4 and a comfortable 255. Not fat by any means, but well stocked. An odd side affect of smoking pot for long periods of time causes cells to grow in a bigger teen males chest, causing female breasts to form. This happened to me starting young, and smoking for a long time. I now have 40c breasts all natural lol, while at first was really uncomfortable, since I now dress a lot it’s really fun!)
As soon as I was 18, I moved out and went to college at Oregon. I spent two years there, learning about business and about myself. I got an apartment off campus and there spent most of my free time and my free money, fulfilling my desire to dress like a girl. I never went out, or let anyone find out. I just studied hard and minded my own business, slowly growing comfortable with myself. It just started with some cheap Walmart panties in a five pack for 6 dollars, where I could buy them and no one asked any questions. I didn’t want anyone finding out, so I just started wearing them under my sweats at home until I fell asleep. Then back to school with my uncomfortable boxers.
By the time I graduated, I had half my dresser and closet dedicated to my inside self. I didn’t have anymore boxers and I wore my panties and bras everywhere, under my man clothes. I still wasn’t comfortable in wearing my girlie clothes out. I got a job offer in Portland, managing a furniture store. I moved every 6 months of so, trying out new apts, til I found a lease and a neighborhood I liked.
After two years, I was at the local community college, taking a spin class, and I saw a flyer forsomeone looking for a roommate. The offer was too good to pass up. The third of rent for a third of a three bedroom apartment condo. I was really trying to save money for a down payment on a house. So this was perfect. I had my own private bathroom and balcony. Separate kitchenette, though I had to share a washer and dryer with the other two tenants. I called the number and met Tiffany and her younger sister Nikki at the college, which was across the street from the condos. It turned out, Tiffany worked and was in school and Nikki went to school for her G.E.D. at the college. Their mom and dad had died, so they were working hard for themselves and needed the extra money.
We got along well enough, but we hardly ever saw each other, because of our schedules. I continued along my destiny of dressing up, heading out to stores that were once forbidden to me, but now where most of the girls working there knew my name. I was there enough lol. I still never dressed up to go outdoors, but loved to sit on my balcony and have a glass of wine, wearing my sexiest skirts and panties. Or clean my apartment in my maids uniform when the girls where at school or work.
The day came, nine months later, when I was finishing folding up my laundry. I shook out a pair of my shorts to hang up and a bright wad of yellow came out of the leg hole. I reached down and picked up the rumpled pair of panties that I knew wasn’t mine. I didn’t have any this color. They must have been one of the girls and gotten left in one of the machines on accident. My first thought was, “wow, these are cute! I wonder who’s they are”? Meaning Tiffany or Nikki’s that is. Tiffany was and still is almost a foot shorter than me, and she’s not fat but not fashion magazine either. She has shoulder length brown hair, a cute, happy smile, and a really beautiful, shapely body, with big but not huge breasts. Nikki though, was 15 at the time. She was tall and slender, taller than her older sister already. She had her long blonde hair to the middle of her back and her sexy little butt and breasts were developing sweetly. Her sweet smile, braces and all, could melt any heart. All innocence and beauty.
By the size of the panties, I knew they had to be Tiffany’s. They were some boy shorts, all yellow, with pink lace around the legs and waist and a pink bow in the middle. I folded them and set them on my bed while I finished with my laundry, intending to take them out to Tiffany in the living room. I was about to, but as soon as I picked them up and the soft fabric touched my fingers, I begin fantasizing about what they would look like on me, how they would feel hugging my curves instead of Tiffany’s. I put them under my pillow and waited til I went to bed, then went to the living room to watch tv with the girls til then.
My skin was crawling with excitement as we said goodnight. I went to my room, locked the door and rushed to my pillow. I took off my sweats and the panties I was wearing, a dark purple and white stripe pair of hipsters ( still to this day my favorite style, so comfy! ) I slowly slid Tiffany’s bright yellow boy shorts up my smooth legs, savoring the soft feeling of the panties and the naughty feeling of putting on someone else’s panties. My sexy roommate’s panties. My small penis jumped to attention quickly. I took of my my hoodie and tshirt, then went to my drawers where I pulled out my favorite pink teddy, slipping it over my head and shoulders. Letting the see through fabric slide down over my soft smooth skin. I shivered and goose bumps filled my arms and neck as I twirled in the mirror on the closet door. My burgundy hair cascaded around my shoulders as I batted my eyelashes at my reflection.
I took a glass of red wine to my balcony and enjoyed a few puffs of my bong as I giggled with excitement. I rubbed myself lightly, through Tiffany’s panties, as I looked out on our back yard. One hand went to my chest, softly caressing my nipples through the silky fabric. Feelings of guilt started to creep in, but were pushed aside as fantasies of being on my knees, dressed sexy like this, pleasing a guy with my mouth. I finished my wine and smoke then went to brush my teeth. I looked in the mirror and smiled, feeling so sexy. I put my long curly hair in pig tails and puckered my lips as I put on my sparkling pink lip gloss. I bent over and looked over my shoulder as I smacked my butt, a slutty smile on my face.
As I climbed into my bed, my thoughts returned to the hard cock of my fantasy. I laid on my back, rubbing myself through Tiffany’s soft panties and I dreamed of my mouth being filled, my pig tails being pulled onto his lap as my throat slowly gets filled. I was moaning, thankful the girls rooms were on the other side of the apartment, secretly wishing they were next door and were hearing me. I quickly came in Tiffany’s panties, realizing too late, being to deep into my dark fantasy, that I needed to pull my small cock out and cum on my stomach, so I could put her panties back clean. Damn I thought groggily, feeling the slickness all inside. I reached my hand down and slipped it inside, my cock shrinking and twitching and it oozed out the last drops of my midnight snack. My hand was covered instantly, sliding between my peach fuzz and the soaked panties. I rubbed back and forth, collecting as much as I could, then rubbed my fingers all over my face. Mmm. I licked my fingers clean, falling asleep with one in my mouth.
The next morning, my day off, I laid there in bed as I thought about the night before. I was so shocked that I had done that. It was amazing and ? And what? I couldn’t think of anything bad. It all felt so wonderful, any thoughts of guilt or remorse washed down last night with my snack. I got up and looked at myself again in the mirror. I had stains all over my face and on my stomach. Tiffany’s panties were still damp on my hips, clinging to my skin. My pigtails were all askew, lipgloss mixed with cum still lightened my lips. I put on my robe, covering up my slutiness, and a beani over my pigtails.
It was Saturday morning and both Tiffany and Nikki had class all day. My thoughts swirled around what I would do for my day off, when I pictured myself going into Tiffany’s room and seeing what else she might have to wear. She’d be gone all day and I just wanted to look. Id take her panties off in a bit and wash them, I felt too sexy to change just then. I checked the apartment, locking the deadbolt and closing the widows and finding no one else there, went into Tiffany’s room straight to her dresser. Omg, I thought. I had my own collection of lingerie, panties and bras and sexy outfits, but seeing another girls panty drawer, so full of different styles and likes than my own, was amazing. I was careful to look at each piece and put it back how I found it, it wouldn’t do for Tiffany to know what I was doing. She really liked flowers and had print bikini briefs, lacy, embroidered silk hipsters, thongs (not my fav, feels like a constant wedgie lol) and several matching bras to go with the panties.
I giggled when I found a garter belt and straps that were yellow and pink lace, matching the panties I was already wearing. I slipped the garter belt up and around my hips. The straps were already attached so I looked in for a cute pair of stockings to match. There towards the back corner of the drawer was my treasure. Under another set was a matching pink and yellow bra, sitting on top of the stockings I was looking for, pink legs with yellow lace trim at the thigh. I was so excited, I was shaking. I took off my pink teddie, tossing it on the bed. The size of the bra said 40d, so it was too big for me, but I put it on anyway,fastening the links and sliding the straps up my shoulders.
I was in heaven. I spun around and danced, my smaller breasts bouncing in the bigger cups of my roommates sexy bra. I eagerly sat down on her bed and reached for the thigh high stockings, feeling my little cock pushing on Tiffany’s panties, growing to its little big size. I bunched up the stocking, putting my toes in the tip as I began pulling it up my thigh. I stood up, pulling it tight, but carefully so I didn’t tear it. I attached the straps of the garter. I bunched up the second and as I was looking down to pull it up.
“Oh my god you dirty pervert”! Oh shit! Tiffany’s voice! My head shot up. I was caught! Tiffany and Nikki were standing in the doorway, shocked looks on their faces. Nikki was shaking her head and laughing, taking pictures on her phone. Tiffany and I just stood there, staring at one another. “Oh god Patrick, or should I call you Patty? Take off my clothes right now you sicko!!” “Wait, on second thought, keep them! I don’t want them, I’d just burn them! Get out now!” I hurriedly ran from her room, grabbing teddy and robe from her bed. Nikki taking pics the whole time. I ran to my room and as quick as I could, took off Tiffany’s bra, panties, garter and stockings. Well at least they’re mine now I thought, for an instant, until my mind cascaded with thoughts on what was going to happen. I got dressed in my own clothes, putting on my own panties and bra under my regular clothes. I was pacing my room when the knock I was dreading came. Tiffany was standing there, arms folded glowering. “Today is Saturday, I expect you to be out of my apartment by Monday morning. I don’t ever want to see you again”. She turned and walked away.
Needless to say, I was out of her place by Sunday night, not wanting to spend anymore time there. Tiffany was there, but stayed in her room while I moved my few things into the rental truck. Nikki was there though, teasing me when she saw the lace of my panties slip up my back as I bent to get more boxes. “Nice panties, sissy Patti. Did you steal those from my sister too?” I just blushed and kept moving until I was loaded. She said Tiffany just wanted the key and me gone, so I gave it to her and didn’t look back when she taunted me as I walked out the door…
More to come! Please comment, so I know what you like. Or don’t. This was just an intro to where my life has been led by Tiffany, Nikki and others. Mostly true, a little I wish, and a lot of fun and excitement are coming.