"Hmmm! Not here." I was naked and looking for my sweats to wear around the house but obviously I forgotten where they were. They weren't in the wash basket or anywhere else I would have expected then to be.
"What about the unexpected places?" I asked myself. "Lori is always taking my stuff."
I started rifling through her dresser and came across a pair of dark blue sweats just liked the ones I was looking for. "She always does this."
I put them on but they feel snug against my naked bottom. I looked in the mirror and saw "Juicy" written across my ass in big pink letters.
"Guess these are hers." I thought. "Although... they do make my ass look nice."
I didn't take them off as I continued going through her drawers still looking for mine. Then I came across her lingerie drawer. I picked up a pair of pink Lycra panties. I paused for a second.
"Nah!" I said out loud and shook my head.
I looked some more. I pulled out a pink lace bra. I know she was a C-cup from when I bought her some sexy lingerie from the sex store. I held it to my nose.
"Mmm!" It smelled of her sweetness.
Again I paused. But this time...
"Why the hell not." I shrugged.
I slipped the loops of the straps over my arms and tried to clip the back like I had seen Lori easily do many times before.
"How did she do this? It's the stupidest way to get dressed." I kept trying. "You need to be a fucking contortionist!"
With sheer determination and blind luck, I was able to hook the eyelets. It was slightly snug. I was pretty skinny and Lori was pretty athletic so it managed to just fit.
Actually it looked pretty good on me. From the neck down, with very fine body hair and smooth skin you really couldn't tell it was a guy. I admired my sexiness in the mirror.
I cupped my breasts and wished they were real and firm. My nipples rubbed against the soft insides of the cups as I pressed them into me.
I looked at the panties again. Being alone in our apartment. "Why not!" I thought. "Lori won't be home for a couple of hours."
I pulled off the sweats and pulled up the pink panties. The Lycra material formed my bum into a nice, smooth and round shape. I had a little bump in the front from growing hard. I stroked it through the soft material which made it even harder.
"Oops!" A little pre-cum leaked through. I pulled the sweat pants back on. Looking in the mirror, I thought "Gee, I'd fuck that if I got the chance."
I picked out one of Lori's pink Lululemon tee shirts. It was a snug fit and crushed my bra cups. "That won't work."
I peeled off the shirt and picked a looser fitting pink cotton one. "Gee, Lori had a lot of pink."
I tucked it in tight enough to proudly show my "tits" without crushing them.
I pranced around the room swinging and swaying my hips and shoulders like those high fashion models on a catwalk, all the time keeping my eyes on the mirror.
"Mmm... Nice!" I thought. "I think I'll just wear these for a while. Who would have guessed I like pink."
I tried to imagine what Lori thought and felt when she dressed up for me in her lingerie. "Girls are so lucky to wear these nice sexy things. Guys should be allowed to wear some too!"
I continued to look through her undies drawer. "Stockings!" Strangely enough, also pink. "I bet these will feel nice."
Some of my favourite time is spent watching Lori dress. I've watched her put on nylons and pantyhose many times. I stripped off my sweat pant again, pointed my toes and pulled the stockings up my legs. It was sheer excitement. I got even harder if that was possible and more juice leaked out of my piss hole.
As I stood, my hosiery kept sliding down my legs. I looked around some more. "Where does she hide them?" I asked myself. "Aha!" I found her garter belt. Guess what colour, "Pink" again.
I wrapped it around my waist. I assumed that the pink rosette went in front. "Would be uncomfortable to sit back if the rose was in back." I surmised.
I had a bit of trouble clipping my stockings, but realized they were similar to my hockey garters.
I smoothed out any wrinkles and stared at myself in the mirror again. I turned my back to the mirror and looked at my ass.
"Ooooh!" I had a nasty thought. I spread my legs slightly and bent over. My panties hugged my bum. The garter straps were taut against the backs of my thighs. The stockings made my legs as sexy as I had ever seen.
It really didn't occur to me to try in any of her street clothes, so I pulled her sweat pants back on again. Just the thought of me wearing her sexy underthings was enough to keep me rock hard. I could have jerked off to ease my sexual beast, but I feared losing this heighten awareness.
"Crap!" I needed to go for a piss. I stood in front of the toilet and pulled down my sweats to mid-thigh so I could pull down my panties and pull out my cock. I then realized that panties are not made to pull down and stretch like that and my boner wouldn't allow me to point it into the bowl anyway.
"No wonder women take so long." I pulled down my panties but they too only went to mid-thigh as my garter straps got in the way. I sat down on the can.
"Fuck!" I screamed as my ass hit the cold porcelain bowl. I got up and lowered the toilet seat.
Sitting, I tried my best to point my stiff cock downwards. The cold shock from the porcelain helped soften it a bit but I was still pretty firm.
After a time, I was able to let a slow, controlled stream of pee go. "Aah!" My full bladder emptied.
I wiped any dribble from my tip. I pulled my panties and then my sweats back into place, flushed the toilet and washed my hands.
Then "BEEEEEEP!" I could barely make out the sound of a car horn. I looked out the bedroom window but couldn't see anything.
"Must be in front." I thought. I started to dash to the balcony but realized I was only in stocking feet. I looked for my slippers but only found a pair of Lori's pink running shoes. The nylons allowed me to easily slip into them. I didn't bother tying the pink laces.
I ran to our private balcony and looked over the edge. Two women were arguing. From the looks of it both of them tried to drive into the same parking space. Hair pulling ensued, as the other was trying to escape by kicking at her opponent's legs.
From my vantage point, they both looked rather young. The blonde wore some shorts and a tube top while the redhead wore a skirt and blouse.
By this time, a crowd of people gathered. Someone tried to incite an escalation. "Fight! Fight!" I could hear one of them shout.
Red grabbed at Blondie's top and pulled it down exposing her sizable, naked tits. Blondie refusing to be embarrassed, ripped open Red's blouse.
I continued to watch until a cop finally showed up to help resolve the conflict. Bastard managed to separate the two of them and calm the situation down. Both of them covered up there exposure.
Suddenly, my sweats were around my knees. "Why are you wearing my sweat pants... For God sake! Are you wearing stockings? And my garters? And my panties?"
"Oh God! It was Lori!" I dared not move or turn around. I really didn't want to show her my breasts.
"What are you? Some sort of sicko?" Lori screamed at me. "Get in here. Now!" I didn't move.
"I said in the living room now or I'll lock you out there." Lori warned me.
I started to bend over to pull up my pants but...
"Oh no you don't! Just get inside." Lori added to my warning.
I turned around slowly. I watched as Lori's eyes grew wider as she looked at my chest. It changed to kind of a surprised look when she noticed how large my breasts were.
"What are you wearing under my shirt?" She started at me with her hands on her hips. "Take the shirt off."
I slowly pulled the shirt over my head and showed her the bra I was wearing.
"Is that my bra?" Lori shouted. "You're wearing my bra. You're just a fucking pervert aren't you? Get in here!"
With my pants still around my knees, I shuffled my feet and stood in the middle of the room. By then, they had dropped around my ankles. My prick was still solid and hadn't gone unnoticed by Lori.
Lori stood there tapping one foot with her arms crossed under her bodacious breasts. "Well?" She looked so sexy in her form fitting, tailored business suit and four and a half inch, high heels.
"I uh.." I pointed to the balcony. "And then..." There was no real explaining why I was wearing her underwear. Lori just shook her head.
"I know you have no shame. Look at that hard on you have inside my panties." She pointed at me. "There's a big wet spot, did you masturbate and cum inside my panties?"
"No, I.." I started, but Lori cut me off.
"Shut up! I didn't want an answer." She yelled at me. "You've ruined my panties you little sissy! Do you think I would want to wear them again after you came inside of my panties? Yes, they are my panties, not yours. Mine!"
Lori stood there glaring at me for a full minute. Then a wry smile came across her face. Her voice was now calm; too calm. "You know...." She started. "You do look kind of cute in my bra and panties." I didn't like where this was going.
She moved to me. Her hand caressed my bum then moved around to my crotch while her other hand reached around and cupped my breasts. She pulled me back and held me hard into her body. I felt her breasts pressed into my back. She started to hump me from behind. A hand stroked my cock through her panties while her fingers pinched and pulled my nipples.
I knew she was going to make me cum. I'm pretty sure she knew as well, but Lori maintained her actions. I wasn't sure if I should warm her of my impending orgasm or just remain quiet. When Lori pinched my nipple hard, it was like an ejaculate button. I started shooting my load inside her panties.
"Uh.. Uh.. Uh.." I grunted. Wave after wave of cum emptied out of my balls. Lori continued to milk me as my jism soaked through the silky material and coated her hand.
Suddenly, Lori grabbed my cock and balls hard. "You stupid little sissy girl!" She shouted at me. "What a mess you've made all over my hand."
She shoved it to my mouth. "Clean it. Lick it off."
I hesitated. Her other hand pinched my sensitive nipple again. "Ow!" I screamed. Lori stuck her hand in my open mouth. I started licking her cum covered hand and fingers clean. She continued to play with my nipple, so it kept me hard.
Lori turned my around and forced me to my knees. She pulled up her short business skirt above her waist. She too wore stockings with garters; her open crotch panties were pink lace. Her pussy lips were plump, red and wet.
Using both her hands on my head, Lori pulled my face into her cunt. I sucked all of her juices that I could. I used my very long tongue to try and dig out more from deep inside her. It was a strange metallic taste different from normal. The smell was a little different too.
"Oh fuck YES!" Lori moaned. "Fuck me deep with your tongue!"
As hard as I could, I reached deep within her. Lori mashed my face into her so hard, I could barely breath.
Suddenly, she pushed me backwards to the floor. She pulled my panties down to my thighs and straddled me. My stiff cock slid into her tight, slick hole.
Lori leaned forward and held my wrists down by my head. Her hips slammed into me. Our stocking rubbed together which was a sensual sensation unfamiliar to me.
"Oh fuck! Oh fuck!" She groaned. "Don't you cum! I need to cum first!"
Her cunt tightened even more. Her walls sucked at me like a straw. I was going to cum!
"Uhhh! Uhhh! Uh.....!" I could not hold back my orgasm. My balls were mostly empty, but still managed to shoot a significantly but smaller load into her.
"No! No! No!" Lori screamed at me as my hard dick immediately started to fade to a soft cocktail weenie. "I told you not to cum! And I didn't want you to cum inside me!"
Lori moved upwards until her cunt was over my face. She faced towards my feet. "Clean your spunk out of me. And don't stop until I tell you!"
The first few dribbles had already dripped into my mouth. It wasn't a bad taste. Again I used my tongue to dig out my sperm.
After I cleaned Lori out, the taste changed. It was no longer a mixture of Lori's and my juices, it was just pure Lori. It started to flow more freely. Lori's breathing became more gasping and rapid.
"Don't stop!" Lori pleaded. "Oh fuck! Don't stop!"
She pressed harder into me. My nose was pushed into her asshole. Her clit rubbed against the stubble on my chin. She was cumming. Her juices poured out of her hole and into my mouth.
"Oooh FUCK! I'm cumming!" Lori screamed as she ejaculated her girl cum onto me. I could not get my breath as she sprayed out like a fire hose. I was literally drowning. It covered my face, went in my mouth and up my nose.
"Oh fuck that was good!" Lori panted with exhaustion. "That was the best cum I've ever had. I've never squirted before."
Lori tried to get off my face, but her legs were wobbly and only managed to collapse on the floor.
"Hack! Cough! Phaa!" As I choked for air.
"Well my little sissy." Lori managed. "I think this could be our new arrangement."
Over the next few days, dressed in my regular clothes, I welcomed home Lori. She had bags of stuff each time but would not let me see or tell me what they were.
Lori hadn't said anything about what happened until I had to go work one Friday. Lori worked from home that day. When I returned, Lori was waiting for me. She was dressed casually in her favourite pink.
I carefully closed the door "Hi." I managed to say and was about to go change.
"Stop!" She ordered. "Strip!"
I looked at her puzzled. "Here?"
"Yes, here. In front of me. Now!" Her tone warned me to obey.
I kicked off my shoes and pulled off my socks. My jacket, shirt, pants and underwear followed. I stood there naked in front of her and waited. My groin started stirring. The blood surged until I had a full boner.
"Stand on those newspapers I laid out." Lori smiled. "Play with yourself until you come." Unsure I heard her correctly, I didn't move.
"Yes you heard correctly. I want you to jerk off until your balls are empty."
Moving to the papers, I tentatively wrapped my hand around my shaft and moved my hand in a familiar masturbation motion. After a couple of minutes, nothing was happening. I was too nervous to cum. I closed my eyes and imagined Lori was playing with my cock but.... Nothing!
I felt a cool liquid hit my chest. I opened my eyes. Lori poured some liquid lube on my body and a liberal amount on my cock filled hand. My free hand immediate rubbed it all into my chest and I tweaked my nipples as I felt that familiar tension build between my legs.
Still it wasn't enough.
Lori moved behind me. She pushed her squirt bottle between my ass and into my hole squeezing the lube into me. That did it!
"Fu..u..ck!" I groaned. The first shot of white creamy cum fired passed the newspaper floor covering. The following huge wads splatted on a picture of Ryan Seacrest.
"Again." Ordered Lori. "Do it again. I know you still have more."
I was still rock hard but I was too sensitive to try and cum again. But Lori stuck the bottle up my butt and juiced me again. A vibrating something quickly followed. It pressed against my prostate. Cum shot out of me like I hadn't come in months until I was firing nothing but air. My knees were shaking, barely able to support me, but I dared not fall down.
Lori picked up my underwear and used scissors to cut them up in front of me.
Next she sprayed some sort of foam all over my body; under my arms, between my legs and ass and over my cock and balls.
It tingled a bit, but it stunk. I stood there for a few minutes before Lori wiped off the foam. "Go shower." She pointed to the bathroom.
I slipped into a warm shower and washed the residual foam off my body. Then I noticed that all my body hair was gone! Not that I had a lot, but any peach fuzz was gone. My tiny, hairless pee pee looked like when I was born.
Lori was standing there waiting and handed me a towel to dry off. Hairless, I felt so naked; so exposed. We moved back to the main living room. Lori had a number of bags waiting for me.
"Since you seemed to like wearing my girlie things, I decided you shall have your own. When you are home, you shall dress as a sissy girl. I will show you how to prepare yourself for me." Stated Lori in a very commanding voice. "Outside, you may wear your ugly boy clothes unless I say otherwise, but underneath shall be your sissy girl undies.
"You can't be serious!" I protested. "What if I refuse?"
"Then you may leave right now." Lori replied calmly. In fact she opened the front door.
"I can't go outside naked, where are my clothes?" I continued.
"Those are your clothes now." Lori pointed at the sissy girl things. "I locked your ugly boy things away. Leave! Go ahead."
There was no way for me to leave either dressed as a girl or naked. Besides, where could I go? My head bowed in defeat.
"Well, are you leaving or do you want to stay?" Lori demanded of me. She was still holding the door open. I saw our neighbour's college daughter walk by. I know she saw me.
"Stay." I stated to cry. "I want to stay."
"Remember, this is your choice. You can leave anytime you like." Lori explained. "But while you are here, you will do as I say."
"Yes, Lori." I sobbed. "I will do as you say."
"Good, now we'll get dressed." Lori smiled at me.
"My colour is pink. I don't want you wearing my things." Lori stated opening the bags and pulled out some things. "You're colour is white. You must keep your things clean and stain free. White will make it easy for me to check."
She handed me the first item. "Put these on."
I held them in front of me. They were pretty, white panties. I slipped them up my smooth legs and up on my hips. They were French cut and made from Spandex. The full panty lifted and supported my bum into a nice round shape. Until I had put them on, I had not noticed the hole in them exposing access to my bum.
"I see you noticed your panties have a little something extra or should I say missing." Lori grinned. "All of your panties are similar for easy rear access except for your thongs. They have a thin string so it won't get in the way.... Much."
Next was a matching white bra. It was fully padded so I didn't require any form inserts. They gave me a nice, full, B-sized cup. It even had fake nipples.
I still had problems trying to hook them closed.
"Some of the other ones are front closures, but you better get used to these." Lori warned me. "I doubt you are really ready for stockings." Lori started. "So here."
She handed me white, cotton, school girl knee socks. "You will need to earn the right to wear stocking and garters."
I pulled them up my legs.
Lori showed me how to fix my hair; how to put on some make up and how to walk like a girl.
Finally, Lori handed me a pair of black Mary Jane's. The thin heels were only 3 and a half inches high, but I still had problems standing and walking as I was just taught.
"You will greet me in the outfit I pick out for you each day." Lori told me. "It is your responsibility to keep it clean, pristine and stain free. I will check. Failure to do so is punishable. Do you understand?"
"Yes." I shamefully replied.
"You will always reply with my name." Lori instructed.
"Yes, Lori." With even more shame.
"Bad sissy girls get punished. Good sissy girls get rewarded." Lori told me.
She led me to the couch and had me bend over. I waited. I heard some rustling but dared not look to see what was going on.
"Twack!" Lori smacked my bum with a riding crop. "That is punishment."
Then she moved behind me and forced my feet apart further. I recognized the feeling of the lube squirt bottle enter my bum. The cool liquid entered me. A more solid and thicker item pressed against my rear entry. Even though I clinched my bum, the lube made it impossible to stop the penetration.