Play Date

(This is a continuation of characters introduced in my previous story "Daddy Party" but works as a stand alone story too.)

I was awakened on Monday morning to a loud knock on my apartment door. Groggily I slipped out of bed and made my way down the hall. Opening the door I was greeted by a woman in a UPS delivery uniform holding a large cardboard box. I signed for the package and she said, "Have a nice day." Before turning and leaving. I carried the box into the living room and set it on the couch. I couldn't remember ordering anything and I didn't recognize the return address on the shipping label but my stomach fluttered as I saw it was addressed to "Jenny." I lived alone and the only people who had ever called me Jenny were at the party Daddy had taken me to the previous Friday. My hands shook as I carefully removed the packing tape and opened the large box. Inside was a neatly wrapped bundle in pink tissue paper with a handwritten note on top. I noticed the flowery feminine handwriting as I read it.

"Dear Jenny. I hope you don't mind, I got your address from Mr. Miller. Amy and I had such a nice time meeting you last week and were hoping you'd be available to come by this afternoon, Amy has been so excited to play with you again. Please be by around 2 pm. The address is written at the bottom of this note. Enclosed is a little something I'd like you to be wearing when you arrive. We look forward to seeing you soon!

Love, Mrs Cooper and Amy."

I'd met Mrs Cooper and Amy at the party last week and had had such an incredible time. The three of us had gotten to know each other very well over the course of that wonderful evening and I felt my arousal level rising as I read her note. My heart raced with excitement as I tore open the pastel tissue paper and laid the contents of the box out on the couch. Inside were a pair of white satin bikini panties with a pink bow and matching bra. White thigh high stockings, black shiny slip on shoes, an assortment of make-up, a bottle of pink nail polish, a blond curly pigtail wig and a frilly satin babydoll dress with cap sleeves and a poofy white petticoat. I felt my shaved cock throb in my boxers. Oh my... I'd been invited for the play date Mrs Cooper had mentioned on Friday and this was the outfit she wanted me to wear. The clothes were so soft and feminine, my hands trembled with arousal as I stroked the shiny fabric of the soft pink dress. I had lots of panties and two school girl outfits but those were kept at Mr Miller's house where he'd have me dress up for him. This was different, these clothes were mine and Mrs Cooper was requesting I wear them over to her house. I'd never dressed up for anyone other than Mr Miller and I was incredibly excited to dress as "Jenny" again, this time out in public. The dress was so girly! I'd never worn anything like it before and couldn't wait to feel it all against my smooth soft skin. I could feel my cheeks flush as I immediately took out the bottle of nail polish and set to work doing my nails.

Once the bright pink polish was dry I hopped in the shower, making sure my body was shaved smooth all over before toweling off and applying my blackberry body moisturizer, leaving my skin incredibly soft. Then I put on my make up. I was getting good at applying it thanks to the YouTube tutorials I'd been watching, making sure it was subtle and feminine, like a good gurl's not like a whore's. I batted my eyelashes in the mirror, admiring my soft pink eyeshadow and plump glossy pink lips and practicing my demure girly smile. I was so turned on that the tight little panties barely fit over my hard cock, the satin sending ripples of arousal through my body as I slipped on my bra and sheer stockings. Next came the poofy pink dress. I slipped it on over my head and wriggled into the soft snug garment, the white frilly petticoat causing my hips to look so full and feminine. Lastly I pulled on the wig, brushing the bangs to the side and smiling, loving the way that the curly blond pigtails bounced playfully each time I moved. I stepped into the glossy Mary janes and buckled the thin straps before stepping back to admire myself in the floor length mirror. The handsome straight guy was nowhere to be seen, in his place was an adorable soft sissy gurl.

My head was spinning, I barely even recognized myself! I looked so cute, so soft and girly. The little dress accentuated my slim feminine frame. I slid my pink fingernails along the soft skin of my exposed thighs between the tops of my stockings and the hem of my dress and shivered, excited and aroused as I spoke to my reflection, "Well hi there, Jenny..."

I called for a taxi and went outside to wait on my building's stoop, my heart pounding as I stood in the crisp daylight feeling the cool air drift up under my dress and caress my tight smooth panty bulge. I hoped that someone would walk past and see me but the street was virtually deserted in the early afternoon and the cab pulled up a few moments later. Hopping into the back seat I gave the driver Mrs Cooper's address and blushed as he looked me over in the rear view mirror before smiling and pulling away. It was a short ride and a few minutes later I was pressing the doorbell of Mrs Cooper's brick town house. There were butterflies in my stomach as I waited, my hands clasped together in front of me as excitement raced through my body. The large heavy door swung open and before me stood Amy. She looked beautiful, her long auburn hair in pigtails and smiling wide in the baby blue version of the same dress I was wearing. Amy was around my age, early 20's I guessed and had a lean, skinny build similar to mine. "Hi Jenny..." She giggled seeing the delighted smile on my face and leaned in planting a soft kiss on my plump pink lips. She took my hand and excitedly led me inside, our petticoats ruffling as we made our way into the hallway and she announced, "Mommy! She's here!"

Mrs Cooper stepped into the foyer of the big town house. She was wearing a thin white blouse buttoned low, showing off her sexy cleavage and a tight black pencil skirt that stopped just above her knees. She was a curvy, middle aged business woman with short reddish hair and black cats-eye glasses. "Hello Jenny..." She said warmly. "Oh my, you look adorable!" She leaned in and kissed me. "Do you like your dress?"

"Yes Mrs Cooper, I love it. Thank you so much." I said blushing as I held Amy's soft hand in mine.

"Oh that's good. You're very welcome Jenny." She said, looking me over, "Amy and I thought you should have something nice to wear for your play date." She stepped back, admiring the two of us. "My my my... such pretty gurls."

Amy and I looked at each other, grinning, hearts pounding as we stood there in our satin sissy dresses.

"Ok gurls, I have lots of work to finish so why don't you two go play in Amy's room and I'll be up to check on you in just a bit, sound good?"

"Yes Mommy." Amy said.

"Yes Mrs Cooper, thank you for having me over." I said

"You're so polite Jenny." Mrs Cooper said smiling and caressing my soft cheek. "You gurls have fun." She turned and headed off into the recesses of the house and Amy led me up the staircase, our girly shoes clacking on the hard wood steps as we hurried upstairs. At the third floor landing I followed Amy into one of the bedrooms at the back of the house. The walls were painted a pastel pink and the whole room emanated an incredibly girly vibe. Everything was a shade of pink! The rug, curtains and the fuzzy comforter on the antique four post bed. Most of the furniture was white but if anyone saw this room, they'd insist that it must belong to a very feminine young lady.

"Wow what a great room!" I said and Amy beamed proudly.

"Thanks, Mommy let me decorate it the way I wanted. I'm only here a few days a week but she thought it would be good for me to have a space that was all mine." Amy explained as she shut the door.

"Has Mrs Cooper been your 'mommy' for long?" I asked.

"About two years?" Amy said. "I used to work at her real estate company but after getting to know each other she decided that she had a job that was better suited for me." She giggled and did a small curtsy and I laughed.

"Oh wow... yes... you're VERY good at this." I giggled as we sat down on her bed. "You look amazing today. I love your dress."

"Thanks!" She said, smoothing the blue satin over her thighs and smiling. "Mommy buys lots of girly stuff for me to wear... I love it. I love being a good gurl for her and Daddy."

"Daddy?" I asked.

"Hee hee... oh I mean Mr Cooper. He'll be home after work. You'll meet him."

My heart raced picturing Amy in bed between Mr and Mrs Cooper and I felt my cheeks flush a bright red. She crossed her legs and let out a soft whimper. "Are you wearing a plug?" She asked.

"Oh. No. I don't have one. Are you?"

She smiled widely. "Yeah... I wear one most of the time. They feel sooo good." I watched as she rotated her hips as she sat and bit her bottom lip. I laughed again.

"They're great. Plus...!" Amy hopped up from the bed and walked to the door, swiveling her hips as she did so before turning and walking back. "They help you remember to do your girliest walk and move your hips, it massages your insides and feels amazing!"

"Oh wow!" I exclaimed. "I have to get one!"

"I have a bunch..." She said. "All different sizes. Do you want to borrow one?"

"Ohmygod, YES. Can I?"

She giggled again. "Of course, come on."

We stood hip to hip in front of her white dresser and she slid open the top drawer. I'd never seen so many sex toys! Massagers, vibrators and dildos, all different colors lengths and thicknesses, dozens of them. I only had one dildo and one vibrator and seeing all of Amy's toys had my shaved cock throbbing hard in my tight panties. I ran my hand over the toys, imagining how good they'd all feel, how sexy Amy must look when she used them on her sweet boipussy.

Amy giggled at my surprise as I stared wide eyed at the assortment of toys and slid her hand around my waist. "I know..." She said, "I have a problem. I can't stop buying naughty toys."

As I looked into her eyes I was overcome with arousal and leaned in and pressed my lips to hers. We shared a long soft kiss before we both giggled with nervous excitement. She slid her long fingers over the toys, stopping on a pink plug about the size of a small pear with a heart on the base. "I think you'll like this one." She said holding it up for me to see, "It"s one of my favorites... it feels sooo good. Plus it matches your dress!"

It felt to heavy in my hands as I inspected the plug, so thick and smooth. I'd never used one before and I couldn't wait to feel it in my smooth boipussy. A naughty smile spread over her face. "Do you want help putting it in?"

I nodded and she took my hand, leading me to the bed, sitting me on the edge of her pink fuzzy comforter. "Lay back." She said as she knelt down. "Get it nice and wet..." She lifted my knees and disappeared beneath my dress. My cheeks flushed again as I slid my lips over the smooth pink plug, sucking it into my wet mouth. I could feel the air on my thighs and Amy began planting small kisses along my smooth satin panty bulge causing me to whimper. She slipped my white panties to the side, exposing my smooth soft boipussy but leaving my cock in the white satin pouch. I gasped as I felt her tongue press against my sissy pussy, taking long slow licks and sucking gently sending waves of pleasure throughout my body, her warm wet tongue massaging me in a way I'd never experienced before. I sucked on the plug, imagining it was the head of an enormous hard cock as Amy ate me out, it felt amazing. Her hand reached up and took the glistening plug, dripping with my saliva and I let out a high pitched squeal as she pressed the tip into me, my legs shaking as the pressure built before the toy popped into place and I shuddered all over. Oh yes... she was right, it felt incredible. Amy slipped my panties back into place and smoothed my dress as she stood and pulled me to my feet.

"What do you think?" She asked.

"Oh my... yes... it feels so good!" My legs trembling as I wiggled my hips from side to side, allowing the thick plug to press against my g-spot. I felt dazed and druggy with arousal.

"Try walking." Amy said and I walked to the door and back, swiveling my skinny hips and squeezing the plug into myself as it sent waves of sexual bliss through my whole body with each step.

"Oh yesss..." I moaned as Amy smiled.

"It takes some getting used to but isn't it so good?"

"Yes... so good..." I moaned, "I feel like such a good sissy gurl..."

Amy laughed and took my hands in hers, pulling me closer and we shared another long soft kiss.

Ever since the party last week, something had changed in me. Dressing as a gurl and embracing my role as an obedient sissy had opened my eyes to what I truly desired. For the first time in my life I didn't feel anxious or stressed, becoming "Jenny" had shown me my true role in life. I loved the feeling of the girly clothes, so soft and tight. I loved doing my make up and hair, shaving my body, making myself pretty and adopting feminine mannerisms. I thought this would all be confusing but it wasn't. I'd never enjoyed the expectations for me to behave as an assertive male, I didn't want to be a woman and I knew I wasn't a gay man but through crossdressing I'd found my place. It had all become so clear that what I truly wanted, who I truly was deep down...an eager obedient sissy boi. I wondered what my girlfriend would say?

I pulled Amy close, my curly blond pigtails tickling my neck as we kissed, breathing heavy and hearing her soft whimpers. She pulled me down to the bed and we lay facing each other, our long sheer stocking wrapped legs intertwined as we caressed each other and sucked softly at each other's glossy lips. It was such an incredible feeling, nothing like with my girlfriend or Mr Miller. Being with Amy, the two of us dressed in our poofy satin sissy dresses, every sensation was so soft and delicate, so feminine. Her soft skin against mine, our hands exploring the other's lean body, brushing her long auburn hair from her face as our lips and tongues gently danced together, I was more turned on than I'd ever been before, in sissy heaven.

Our dresses had slid up as we gently rocked our hips, squeezing our plugs and pressing our thick smooth panty bulges together. Sex had always been a stressful endeavor, so much pressure to stay hard and be in control of everything but here with Amy, everything was so soft and natural, so freeing. I was able to embrace my true self, letting go of everything and being fully in the moment. Feeling her hard panty cock sliding against mine, more aroused than I'd ever been before as we kissed and I inhaled her sexy perfume.

We gazed into each other's eyes as we slowly gyrated our smooth hips and Amy ran her fingers through my curly blond hair. Her cheeks were flushed a bright pink like mine and judging by the thickness of her erection I knew she was having as much fun as I was.

"I love this..." I whispered.

Amy nodded, "Me too..." before kissing me again, a swirl of passion racing between us as we gently humped and sucked at each other's tongues. "It's so much better like this... so much better to be a sissy..." she whispered as she gently sucked my earlobe.

We stayed like that for a while, kissing, caressing, gently humping and letting out soft girly moans.

"Wanna try something fun?" Amy asked and I nodded enthusiastically. Whatever she was thinking I knew I'd say yes. Like a good sissy.

She hopped up and went to the dresser and pulled out two thick articulated dildos with suction cup bases, a lavender one and a blue one, both about eight inches with smooth thick heads. I knelt and watched as she came back to the bed and stuck the toys to the headboard before climbing back up and pulling the two large pink satin pillows from under the comforter, handing me one. She straddled her pillow and got down on all fours. Her dress flipped up in the back revealing her tight smooth ass in her powder blue satin bikini panties.

"Daddy taught me to do this when he's not around... for practice." I watched her arch her back and take the blue dildo between her pink glossy lips. She began sucking it, slowly working the head and humping her thick bulge against the soft pillow. She looked so sexy and I immediately followed suit, pushing the pillow between my thighs and kneeling down beside her. I flipped my petticoat up in the back and closed my lips around the purple toy in front of me. Mmmm, it felt so good in my mouth as I pumped my lips up and down, sucking the thick toy as I humped my hard panty bulge against the satin pillow. Amy was whimpering as she humped and sucked and soon I was too, both of our tight sissy asses up in the air, our big gurl cocks throbbing in our soft panties as they slid against the slippery soft pillows. She took my hand in hers and we gazed into each other's eyes as we sucked our toys, imagining they were real cocks, milking them with our wet eager sissy mouths. Each thrust against the pillow caused the plug to press into me, filling me with pre orgasmic joy as my cock rubbed against the soft satin of my panties. We looked so hot! So naughty and sexy as we humped away, two good gurls playing together and sucking the big rubbery cocks. I kept a slow rhythm, dragging it out, enjoying every minute. Amy was doing the same, our thrusting shaking the bed and filling the room with the sound of our soft sissy moans.

It all felt so good! I had let go of my inhibitions and submitted to my desires. Amy looked so beautiful and I absolutely loved that we were doing this together, both of us completely in the moment humping and sucking like good gurls. My head was spinning, I felt hypnotized and sex drunk, dizzy from the sensation of pure ecstasy coursing through my entire body.

Suddenly my haze was broken by a knock at the bedroom door. A man's voice said, "Gurls, are you decent?"

I froze and looked at Amy, the dildo still between my lips as my heart raced.

"It's Daddy!" She whispered, "Don't stop."

I resumed humping and sucking, embarrassment creeping in, knowing we'd been caught like this but at the same time not caring. Excited to meet Amy's "daddy" and for him to see us like this in our pretty dresses.

"Come in!" Amy said before sliding her mouth back over her dildo and continuing to thrust her hips.

I heard the door open and footsteps nearing the bed. My cheeks were beet red but I didn't stop pumping my smooth hips, it felt too good. My pleasure mixing with the excited shame of being caught.

"Oh yes... that's what I like to see." The voice said. "Good gurls."

Amy and I looked up to see Mr Cooper standing by her side of the bed. He was a tall man in his fifties with light grey hair and a smooth chiseled jaw. He wasn't wearing a shirt and his toned muscular chest and stomach looked amazing. He wore only a pair of tight short black boxer briefs that barely concealed his massive bulge.

"Hi Daddy." Amy said with a smile. "You're home early."

"Hello Amy. Mrs Cooper called and told me you had a friend over and I thought I should cut out early to come say hello."

Amy rose to her knees and wrapped her arms around his neck as she kissed him deeply and his large hand cupped her backside. He gently guided her head back down and she resumed sucking her dildo as his hand slipped over her smooth tight ass, massaging her plug through her panties causing her to moan.

He then made his way around the bed and I could feel him standing beside me as I pumped my lips up and down the thick shaft of the dildo. He placed his hand on my chin, the toy slipping from my mouth as he guided me to my knees. I looked up at him, catching my breath.