Super Surprise Ch. 01

Story Info
Meeting a new friend turns into more than she bargined for.
2.8k words
4.3
53.3k
11
0

Part 1 of the 2 part series

Updated 10/27/2022
Created 01/10/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I was worried when I got the phone call at 5pm that she was canceling, but it was much better news. Emily, my new friend I met on one of the BBW dating sites, was just calling to tell me that one of her friends, Rita, was going to be at the bar with her and she was up for some fun too, if we all clicked.

I was very excited at the idea and quickly said that it wouldn't be a problem. We made sure that we were meeting at the bar at 7pm and that we would have some fun.

I started to get ready, excited to meet this woman that I had been flirting with online for a few weeks and now this new woman as well....it could prove to be a very interesting evening. I quickly showered making sure I shaved my pussy so it was nice and smooth, just in case someone got to touch it or see it tonight. I soaped up my breasts, making sure the sweet smelling shower gel was massaged into my aching nipples.

I quickly dried off and put on my lotion, loving how sexy it smelled and how soft it made my skin feel. I dusted on some of my sparkle powder on my chest and over the top of the make up I had applied to give me a little extra glow.

I put on the garter belt and stockings deciding to forgo panties in hopes of not really needing them, and slid on my lacy black bra. I slid on the knee length black skirt and the black top that held my breasts tightly and a sheer silver shirt over the top. Looking in the mirror, I knew I looked good and hoped I looked good enough to eat....

I got to the bar with about ten minutes to spare and not seeing Emily I found a nice table that was easily visible and ordered a beer to try and calm my nerves.

About 10 minutes after 7 I see Emily come through the door with a wide eyed young lady trailing after her. Emily looked wonderful, she was about 5'10, a beautiful pear shaped BBW wearing a dark blue dress. Her brown hair was pulled up into a loose clip on the back of her head and her blue eyes sparkled when she saw me at the table.

The young lady with her, who I assumed was Rita, was a BBW as well though not pear shaped, she just was a bigger girl. She was blond and pale with greenish/hazel eyes that looked like she was a deer caught in the headlights. She was a few inches taller than Emily's 5'10 and filled out her long black dress quite well.

I stood and hugged Emily hello, excited to finally meet my new friend in person. I was introduced to Rita who blushed and stammered a quiet hello. We all sat and started to chat like we were all old friends, talking about movies and tv shows and music....anything we could think of. Rita was shy but spoke up when she was asked a question or had something to say.

After sitting there for about an hour, Emily asked if I would be interested in going to her place and chatting somewhere quieter. My pussy tingled and I agreed. Emily told me that if I wanted she could ride in my car with me and Rita could drive her car since she knew the way in case we got separated. We walked outside and got into our cars and I started to follow Rita.

I chatted casually with Emily on the way and told her how excited I was to make some new friends and how excited I was about the possibility of more. She smiled at me and said that she was too. She slid her hand on my knee in a comforting gesture and started to rub it up and down. I smiled at her and kept driving as she caressed my leg and as she started to pull my skirt up inch by inch. My breathing was getting heavier, I was enjoying the feeling of her pulling my skirt up, wanting to feel her hand on the bare skin above my stockings. I shivered as she touched the bare leg.

"Were almost to the house" She said "I want to touch you first, can I?"

I nodded.

She unfastened her seatbelt and turned on the seat. Using her right hand she played with my stocking tops and the garters before she moved to my thigh and came so close to touching my over heated pussy that I moaned and shifted in the seat.

She giggled and slid her middle finger once up and once down my dripping wet slit making me groan in need.

"I think you are ready for some fun tonight sweetie" She said to me smiling. And refastened her seatbelt she didn't say a word the rest of the way there.

We finally got to Emily's house. Getting out of the car, I silently thanked the Goddess that I didn't crash when she had touched me. We all went in and got comfortable with some wine and some snacks.

The conversation slowly turned sexual, talk of hot guys and who we thought was the best hung and how hot certain things got us....and then we started talking about what we liked about women....We were sitting kind of close together on a large sectional couch and Emily slid over to me and ran her hands over the swells of my breasts ever so gently and added that she loved the feel of a womans breasts, so soft yet so firm and luscious.

I agreed and ran my hands over her breasts as well, loving the feeling of her hard nipples poking out against the fabric of her bra and dress.

Rita excused herself to the ladies room and said that we were grown ups, we could figure out what to do while she was gone.

Emily and I faced each other and smiled. We gently leaned forward and started to kiss, slow closed mouth kisses at first but turning into passionate open mouthed kisses with our tongues dueling, trying to taste as much of the other as possible.

Our hands started to roam each others bodies, touching anything we could. She got both of my shirts off and was touching my breasts through my lacy bra before I decided I wanted to get her dress off.

I pulled back and asked her to stand up, as we stood together I lifted the dress off of her and over her head. My hands went to her breasts that were barely covered in her black lace bra. I touched and groped, loving the feeling of her warm tits in my hands.

I pulled one out of the cup of her bra and started playing with the nipple.

"Oh yes" She moaned "I need to sit, that feels just too good"

I laughed and sat with her on the couch continuing my assault on her hardened nipple. I leaned forward, our bellys rubbing together, and took that hard bud in my mouth. I suckled on it and gently nibbled on it as I worked her other breast out of her bra. Once it was free I switched nipples, suckling and nibbling on the other as my fingers pinched the other. I reached around and unfastened her bra, releasing her beautiful tits so I could hold them better.

She moaned and writhed under me as I licked and sucked on her nipples like they were my last meal.

My hand slowly started to roam over her belly, rubbing the soft skin, loving how she felt. My hand moved lower and lower still until I felt the opening in her crotchless pantyhose.

I felt the heat and the moistness without even touching her. She gasped and said "Please touch me, touch my pussy Stacey, its on fire for you."

I slid my fingers into the hole of her pantyhose and found her shaven pussy just dripping wet. My fingers played with the wetness of her pussy before slowly parting her lips and sliding my fingers up and down her wet slit. She groaned and ground her pussy against my fingers.

I found her clit and started rubbing it gently in great big circles. "Oh fuck yes" she moaned.

I decided to get more bold and stopped my oral assault on her nipples and my probe of her clit. I slid to the floor in front of her and took her pantyhose off. I spread her legs and looked at her hot wet pussy. I leaned in and took a taste and her pussy tasted so good. I started to lick up and down her slit, trying to touch every inch of her pussy. I started flicking my tongue on her clit and she started going crazy. Her hands wrapped in my hair, pulling me into her pussy, keeping my tongue glued to her clit. I kept flicking my tongue on the hard bud but I also took some circles around the little nub making her squirm.

"Fuck Stacey, make me cum....lick me and make me cum all over your face."

I kept licking and slid a finger in her hot wet slit. She shuddered and came, her juices leaking out around my finger and coating my face.

Her hands relaxed in my hair and she told me to come up and kiss her.

I sat next to her on the couch and started kissing her again. "I love tasting my pussy on you." She sighed.

Her hands went to the clasp of my bra and started to unhook it. She threw it off and started touching my breasts and playing with my overly sensitive nipples.

I started moaning for her, loving how she was touching me, aching to feel her touch my overly excited pussy. I didn't have to wait long....

She got on her knees on the floor and pulled my skirt off and opened my legs. She dove in and started to lick my dripping cunt. Licking much like I did, trying to touch every inch of my pussy with her wiggling tongue. She slid two fingers in me and started pumping them in and out before she even touched my clit...I was so close that I knew when she touched my clit, be it with her tongue or her fingers, I would cum so hard for her.

Her tongue circled my clit, not giving it the pressure it needed to go over the edge, but teasing it, tempting it with that sweet tongue. I was moaning and my hands found their way to her head. I started petting her like a puppy, loving the feel of her soft hair on my hands as she was working her magic with my wet pussy. After what seemed like an eternity she took my clit into her mouth, sucking hard and started flicking it with her tongue as she held it captive....I couldn't hold back. I came hard and fast bucking my hips up to keep her fingers in and keep the suction on my clit....I came almost screaming because of how badly I had needed the orgasm. But she didn't stop....she added another finger and kept going....extending my orgasm building me up to a bigger one....

My hands went to my breasts and started pinching my nipples. I was grinding my pussy into her face when the second orgasm crashed down on top of me. All I said was "FUCK" and shook under her hands and mouth.

She let go of my clit and slid her fingers out of my pussy. She sat on the couch and leaned into me and kissed me hard and deep. I loved my taste on her mouth.

As we recovered I asked "Where did Rita go Em?"

"Oh she'll be back, probably heard us having fun and didn't want to interrupt. Ill go get her."

After a few minutes a blushing, fully clothed Rita entered the room. "Emily went to get a quick shower to freshen up. Looks like its just you and me."

"Do you want me to get dressed?" I asked, not wanting to make her uncomfortable.

"No, its quite alright" She smiled and sat on the couch next to me. "I wouldn't mind it if you wanted to get to know me a little better either."

I noticed she sat down so her skirt was high up in back...I had a feeling she wanted me to take the lead and start touching her.

My hand started rubbing her skirt on her thigh, slowly pulling up the material. Once it was up to about her knees she took my hand and kissed it and slid it under her skirt.

My hand roamed over her knee and up her thigh I felt the hot cotton of her panties...but I felt something else too....

I started to rub the front of her panties and she moaned for me....but I wasn't rubbing a pussy...I was rubbing a throbbing cock that was trapped inside the tight cotton panties.

I started to pull my hand away but she grabbed it...."Please, don't stop...I will explain but please don't stop touching my cock."

I left my hand in place as his cock throbbed through the panties. "Explain, now"

"I have this little kink," he explained, "I enjoy dressing up like a woman and Emily likes it too. She told me about your meeting tonight and what might happen and I begged to be included. She told me the only way I could go with her was to dress like a woman so it wouldn't freak you out. I have practiced for a while to get the walk and the voice down and I really wanted to try. Please, don't be angry, it was me who pushed her to let me go."

My hand started stroking his hard cock again through the panties.

"Ohh, yes. Please don't stop. I watched you two make each other cum, it was so fucking hot....I begged Emily to touch me or let me cum but she said that only you could get me off...and if you forgave me for being a bad girl I was to do whatever you wanted me to do the rest of the night. Mmmmm, yes....it feels sooo good."

I stopped rubbing his cock and told him "Stand up and take off your dress....I want to see you."

He quickly stood and took the dress off over his head. He was standing there in a pair of tight cotton panties and a nice lacey bra...no falsies it was all man boob and so fucking hot. He had knee high stockings on because of the long dress and looked kind of silly standing there in them.

"Take the socks off and stand there for me."

Quickly he took the socks off and stood there in front of me. His cock straining against the cotton. I leaned back on the couch, just looking at him. I started to play with my breasts, pinching my nipples, loving how his eyes glazed over when I had started to touch myself. His cock started throbbing harder in his panties, he started to touch it and I told him to stop. "I didn't tell you that you could do that, did I?"

He moved his hands away and shook his head. "Watch me then, no touching."

I kept playing with my nipples, pinching and twisting them and I moved one hand down to my dripping pussy. I started to play with just the slit. Teasing my finger up and down it. I moaned and he groaned, I notice a small wet spot on his beige panties. I start to play with my pussy more, sliding fingers inside of me, working my clit with my other hand. Im so very close to a huge orgasm when he groans and starts to thrust his hips and the small wet spot turns into a big wet spot as he cums in his panties while watching me.

That sends me over the edge and I cum as I pound 3 fingers into my hot pussy.

I come down from my high to see his red face. "Are you ok?" I ask, concerned about him.

"Embarrassed" he says "Ive never cum in my panties like that without being touched, it was amazing."

I smiled and stood on shaky knees and started to rub his still hard cock in his cum soaked panties. "I'm sure we can have some more fun tonight if Emily wants and says its alright."

He moaned and nodded.

"Why don't you go find her and we will see what trouble we get into."

He obediently went to find her as I collapsed on the couch happy at my luck in finding the special surprise inside those panties....

Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
My Girlfriend's Mother Has a Secret He's caught spying on his girlfriends mother.in Transgender & Crossdressers
More Stories