Looking for Tess, Dressed just So

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

"So you've been thinking of me huh? I had trouble focusing at the meeting as well. I love looking into your eyes as you love my clit with your mouth and tongue." We were moving just a bit, she pulling out only about two centimeters of her clit.

"Now I think your throat is ready. I'm going to fuck you."

I gave a smile with my eyes and she began, just a bit further out and slowly since my throat had grabbed her length. My private practice had enabled me to breathe without panic through my nose. Tess smiled and caressed my face and hair as she increased her rhythm. Then I felt her turning the plug with her other hand, slightly extracting it from my bum only to release it and allow my ass to seal around it again.

"So now you get to enjoy my seed," she said just as she erupted when her clit was fully back in my throat. The amount of seed wasn't great but some did escape my mouth. She bent down and kissed me cleaning the dribble from my cheek.

"I hope I'm everything you expected Maddy. I'm falling in love with you."

I reached up and hugged her while she continued to play with my butt. I moved to stand and we kissed, our mouths wide and our tongues intertwined. The heels made me taller by almost five centimeters. I felt the fingers of her right hand rimming the edge of the handle protruding from me while her left caressed my breast. She stopped and bent to pull my thong away leaving it dangling near my knees. My body was very aroused and yet I wanted to focus on hers. I slid the left strap of her Basque off of her shoulder exposing her breasts and I leaned to kiss the nipple of each.

While I worked my tongue at Tess's nipples her fingers were now sliding about my vulva using the moisture to further open my bum. I was surprised how comfortable I had become with using my anal passage for sexual pleasure. Tess's initial attention was the event that truly opened me. Her gift of a stone plug had so surprised me. The forwardness of the gift, the assumption of control, was what had brought us to today.

"Should I enter you or would you like to fuck me?" she asked.

I was happy with her suggestion since using her Realdoe had been one of the highlights last night. "I would love to be inside you Tess. When you had to leave it's all I could think of, me fucking, you fucking, humm."

She smiled, "I'd love to be fucked so let's go to the bedroom." She removed her fingers from my plugged opening and turned toward the other room.

"NO, I want to take you right here Tess. Settle yourself on the chaise while I attend to my cock." I pushed her slightly to clarify the role reversal.

"I hope you're moist enough. There, you have an assignment."

She understood and did exactly as directed and I noticed her beautiful hose' and heels.

"I do love your CFM's dear, and the way your ass is framed by the straps and hose. I intend to enter you from the rear, get yourself ready." Before walking slowly off in the tall heels I bent and kissed and licked her cleft.

I recovered the insertable from the floor just beneath the bed skirts and washed it. This dildo was the stout version and fit snuggly in my honey pot. We had agreed to generally fuck with our thongs in-place. This seemed to help Tess feel more womanly, her clitty a bit concealed. It also aided retaining the inserted phallus. I stepped quietly to the doorway to inspect Tess. She had placed a large red pillow atop the chaise that lifted her rosebud to a perfect angle and height. I paused just watching. She had clearly used her mouth to lube her passage, as I saw the spittle glisten. Her knees were spread a bit and the heels showed a bright red sole. She had one hand on her bum holding the cheek wide open. I almost ran to get my phone for a snapshot. Her breasts were relieved from the Basque, which was taut across her sloping back and I studied the detail to distract myself as well as provide a delay. She needed to learn patience as well as I did.

I moved slowing across the floor, my noisy heels making my presence known while I lubed the cock. I intended to not pause and the speed I walked toward the chaise allowed me to consider the aim and angle of my penetration. I noticed that Tess worked to keep her eyes looking out the glazed wall. There would be no surprise but the anticipation made me very aroused. As I reach the carpet edge I carefully held my cock and moved the last steps without a sound.

"Uggh! Madeline, yes, ohh, ohh, ahhh, so big my lover, more, more, deeper please."

I rode her for a few slow strokes pushing into her hole then I adjusted my pace as she relaxed. The large plug was still within my bottom. It banged the end of my insertable through my inner wall as I moved. I pulled her right heel covered foot toward me to help steady the action. I noticed she had her left hand at her clit bump and was tapping it with our rhythm. My half of the fun stick was bringing me closer to peak but I wanted to watch her sunlit face as she came so I slowed my thrusts and moved her first to her left hip while pulling her down toward my cock a bit. Then I shifted her to her back.

I could now look into her eyes as well as watch her breasts heave. I grabbed both of her hose' covered legs bringing them together and high above her bum. Now I was certain we were both near and I could fuck her fully. I pushed into her tight bottom deeply. The plug and the deeply settle end of the realdoe were causing me serious joy. Her sighs changed to moans and her breathing was sharp. I was so wet but also sweating from the excitement.

I was growing a little tried and accidentally allowed the cock to slip out of her butt. I used the pause to lie on my side, still able to get at her hole and we proceeded to fuck. Tess held her bottom a bit and I grabbed her waist to better penetrate my babe. I decided to slow for a full 20 seconds. She would be so close but I would have her even more excited when I plunged deep again.

"More, more lover, fuck me now, I want your great cock . . ."

As I started the last push into her I'd moved my hands to her breasts and she screamed and grabbed my neck pulling me to her mouth. I started to orgasm at this moment and a loud groan of intense joy came from my mouth as we kissed. Her seed oozed to her tummy while I held my fake stick deep inside her ass. I was again surprised by the intensity of our sex. The act of fucking Tess had re-leveled the relationship; she was my bitch.

"Aren't you a lucky girl Tess. Someone loves your bum three time in less than a day."

We remained somehow atop the chaise for a while longer. We kissed and snuggled not wanting the bliss to depart.

"What's next for your day dear?"

She smiled as she turned to kiss my mouth, the realdoe cock slipping from her hole. Then she pushed me to allow her to pull the plug out and I moaned deeply again.

I considered the requirements for dealing with the telcon I had on the schedule. "Do you want to accompany me to the office?"

The End

By Madquill

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
MadQuillMadQuillover 8 years agoAuthor
MadQuill's follow-up Chapter(s) to "Looking for Tess, Dressed just So"

Visit the author's pages and find Dressed So Chapter no.3, The girls meet a new Master. There are four additional stories; Chapter no.4, Dressed So History; Tess recalls her Development; Chapter no.5, The story continues as Louisa meets Charles; Chapter no.6, More of Tess' notes for the story "Dressed So"; and Madeline in Oregon, Madeline visits her dying Aunt

AnonymousAnonymousover 8 years ago
Thanks for sharing this

The theme and plot kept my interest throughout this story. Is there a second chapter coming?

Share this Story

Similar Stories

The Researcher A scientist is introduced to her Mistress.in Lesbian Sex
Dressed So A beautiful lesbian finds love.in Transgender & Crossdressers
The Flight Heather leaves home and a new future.in Transgender & Crossdressers
The Flyer A college boy leaves home and a new future.in Erotic Couplings
The Bar Pt. 01 Jessie decides to meets some girlfriends.in Transgender & Crossdressers
More Stories