Wonderland

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"Angela", I replied quietly, it's nice to meet you."

"Don't be nervous dear. Let's have a look at you," Brenda said as she appraised me with piercing eyes.

To Mistress, she said, " nice tight trim body, round bottom, I got the size I think, and a few ideas. I know black is the color of choice these days, but I am thinking something lighter in a pastel shade, with matching stockings. Yes, I think that would contrast nicely with Angela's natural coloration. "

She continued talking herself mostly, " hmm, clingy to show off the trim body and yes, a halter top."

"Angela," she asked without missing a step and pointing at my chest, are you taking hormones, do you have natural cleavage or are these just padded up?"

"No, no hormones Brenda, just padded," I stuttered.

"Angela, relax please," Brenda said. Turning to Mistress she continued, "I do think a halter top would work better than something strapped and I have a few different colors including black if you want to go that way. Why don't you take Angela to my office area and I'll bring back some choices. It will be private there and help Angela here to calm down."

Mistress responded, " I trust your judgement Brenda. Don't be concerned about Angela. This is her first time out publicly."

I did calm down for a moment once we were in Brenda's office.

Mistress, said, "Angela you might as well remove your sweater and skirt. Brenda will be back in a moment with dresses to try"

By now, I knew I shouldn't hesitate and I removed my sweater and skirt.

"What's this," Mistress questioned, while snapping the elastic on my thong."

I started to explain and Mistress cut me off.

"It was a rhetorical question, Angela," Mistress continued. " I know what it is; good elastic and pouch. It should keep everything in order; good choice."

Brenda returned with several dresses and gave me the once over again. Dressed in only bra, thong, garter belt and stockings I felt as vulnerable as the first time I stood In Mistress Sera's living room.

"Hmm," Brenda said, I see you shave and peel your butt and private parts but you must shave and peel your chest and arms to wear a halter dress." " We will also need a different bra. We can't have straps showing. I have just the thing that will work. I'll be back in a sec."

Brenda soon returned with a strapless bra fortified with extra padding. When I put it on, I could see I was bustier than I had ever been.

"Oh," with boobs like that and a sexy dress, you'll be very hot," Brenda said to me with a smile.

We settled on a lilac colored dress with matching stockings. As we were leaving, Mistress turned to Brenda and asked, "will you be able to join us next Friday evening?"

"I was planning to and now that I know Angela will be the guest of honor, I certainly will be there," Brenda replied while raising her eyebrows and shooting a smile towards me.

Chapter 7

The Friday soiree was what I thought it would be; much drinking which quickly transitioned into a suck and fuck fest. I was doing the sucking, of boobs, pussy and dildos depending on what was being presented to my mouth at the moment. The half dozen women, which included Darla, were doing the fucking instructed by Mistress Sera. My pretty cocktail dress spent most of the evening pulled up as I was bent over or put on all fours.

Mistress could be heard giving instructions. "Make sure her pussy is really lubed up," Mistress chortled. "Penetrate slowly and then you can pound away. Don't worry Angela won't break and sure go ahead and smack her ass if you want."

The women on their part made comments such as "this is so much fun," " if my ex let me do this we might still be married," and " have to find my own friend like Angela, this is such a turn on."

To be honest, it was a major turn on for me, albeit exhausting. The strain on the cup of my thong from my stiff cock must have been obvious.. I like foreplay as much as the next man or woman, but at some point you have to each the proverbial happy ending. However, no one seemed to care whether I climaxed.

The one woman who did not participate in the festivities was Brenda. She sat by with a bemused look sipping wine. I imagined that this was all a bit much for such a refined woman and she was biding her time as to when she could make a polite exit.

As the evening started to wind down and there was a lull, Brenda came over and whispered in my ear, " Angela, you are a bit of a mess." Why don't you head to the bathroom and straighten up some and then meet me in the back bedroom."

Mistress observed this exchange and I saw her shoot a knowing look at Brenda. I thought to myself maybe Brenda just wants an old fashioned fuck. She was certainly attractive enough and in my state of arousal I would be happy and grateful to fulfill her wishes.

Brenda entered the bedroom and walked straight towards me. Putting her arms around the back of my neck she kissed me pushing her tongue deep into my mouth. She lingered for a time kissing me deeply while one hand slide down to rub my swollen member. She guided me backwards to the bed where I sat down. Brenda stepped back and slowly undid the buttons of her blouse exposing her perky well rounded breasts. She cupped her breasts with both hands while teasingly saying, "Angela wouldn't you like to have a taste of these?"

She unhooked her bra and pushed her tits towards my mouth. I greedily massaged and sucked away as Brenda's encouragement continued. She pulled away somewhat abruptly and declared," I need to fuck Angela."

She turned her back towards me and unzipped her skirt, letting it fall to the floor. She rolled down her hose and hooked her thumbs into her panties and slid them off. Brenda's ass was firm as were her legs, firmer than I expected given her age. She must work out I fleetingly thought.

Brenda turned back toward me slowly and I was confronted with a fully functional, tumescent, cock. Surprise was a mild way to describe my reaction. I simply had no idea. Before I had a chance to react, Brenda grasped the back of my neck again and pulled me towards her gleaming cock and pushed it forcefully into my mouth.

"Suck it Angela," Benda commanded. And suck away I did. I could tell her excitement was mounting by the pace and force of her thrusts and her increasingly loud vocalizations.

Brenda pulled her cock from my mouth and pushed me flat on to the bed. She reached into the night stand and pulled out a tube of lube and applied it to her cock. Standing over me she said with urgency in her voice, "Angela roll your legs up and spread them. I want to see your pussy."

Again I had no time to react as she grabbed my legs and moved me into position. She really did need to fuck, just not in the way I had expected. She inserted a finger into my pussy coated with more lube and then slowly guided her cock to the target. With one hand, Brenda freed my cock from its pouch and placed her thumb just under the tip on the glans and began to slowly rub as she penetrated me.

She started thrusting slowly while she continued to rub my glans. Her pace increased and my excitement increased accordingly. And then, she stopped.

" Jesus, Brenda," I said hoarsely, don't stop, please don't stop."

"Angela, be a patient girl, she replied, " I want this feeling to last for both of us."

Shortly, she resumed her thrusting, increasing the rhythm and force. My hips were pumping to meet her every thrust and I wrapped my legs around her

"Brenda," I gasped, "oh baby, I am going to explode."

Brenda did not reply. I could feel a shudder and with one final deep thrust, I felt her jizz filling my pussy, just as I came hard, feeling the warmth of my semen as it jetted up onto my stomach.

We lay together with Brenda still inside me, spent. Brenda, after several minutes withdrew her now limp cock from me and I felt her semen drain out between my legs.

"Lay here," Brenda said. "I will be right back."

She returned with a damp warm wash cloth and cleaned the semen off. She then climbed into the bed beside me.

"Lay back," Brenda whispered as she put her arms around me." "Rest now dear, rest."

The next thing I knew was rays of sunlight were poking through the drapes. I was still in bed with the covers pulled up around me. Brenda was gone. I dragged myself up feeling weary; not hungover as I had very little to drink, just wrung out. Draped over a chair in the corner I noticed a pair of leggings and a sweat shirt. I padded to the bathroom and removed my dress and wig and took a hot shower. Returning to the bedroom in a towel, I realized my dress was a mess and would have to be cleaned. I picked up the leggings and rolled them on and pulled the sweatshirt over my head. I decided not to get made up or put the wig on.

I walked to the kitchen following the aroma of coffee. Mistress, greeted me." Good morning sunshine", she said cheerily. " My leggings look good on you. You should buy a pair." I understand your evening ended with a bang."

"Very clever Mistress," I replied dryly. "Hey, who do I have to suck off now to get a cup of coffee?"

"My, my, a little chippy this morning are we? The coffee is on the house," Mistress said. "You earned it. Come on, though, tell me you didn't have a fun time."

I hesitated a moment and then replied, "Mistress Sera, you set me off on a journey and sometimes it seems like a dream, a wild and strange dream at that." And like Alice, the journey you've sent me on gets curiouser and curiouser.

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3 Comments
Kathryn65Kathryn65over 1 year ago

I really liked this story Angela’s Mistress was almost sympathetic and no where near a domatrix which made the whole story much more appealing to me, the shop keeper was a wonderful twist and climax for all concerned. Thank you kindly for sharing your skill and craft with us all.

AnonymousAnonymousabout 2 years ago
New Dresser

It was now time for me to go public as the woman i now am.My body now is more female then male.Long hair slim waist breast firm butt and now a hair less body.The woman next door has helped me with make up and dressing.She has fixed me up with her friend for my coming out night. The night went well until we went back to his place.Once there he was all over me kissing feeling me up.He forced my hand down his pants to feel his hard cock.I tryed to get away but he was to strong.Soon my dress and thong was off and he was fucking me hard.Telling me i was now his new girl friend.H was going to make me in to a real woman.He fucked me and forced me to suck his cock.Later he tied me to the bed and used me for sex for the whole week end.

KrissyfurKrissyfurabout 2 years ago

I really enjoyed this story. Hopefully this will be a multi part series. I’d love to hear more about Angela’s journey.

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