Wonderland

Wonderland

Chapter 1

I am sitting at a nice restaurant with a friend for luncheon. I can see we have attracted the attention of two men sitting at the bar who keep shooting glances at us. Of course appearances are not always what they seem. My friend is actually my Mistress, Mistress Sera. I am a fit, middle aged man. I am dressed in a tight fitting short black skirt, black hosiery, and an off-white fine knit sweater. My nails are polished and my black pumps are low heeled. The low heels are a blessing for me as I cannot understand how anyone can walk in six-inch stilettos.

Underneath, my cock is firmly secured by a strong, lacy elastic G- string designed for the purpose. Mistress has told me it is necessary when wearing tighter clothes to be constrained as such, in the event I don't mind my manners. My bra is plus sized to better fit my frame and heavily padded. I certainly do not appear flat chested. The last item underneath is the small butt plug inserted in my "pussy". Mistress likes me plugged, I think, mostly because it amuses her. It also acts as a reminder to me of who is in control. Finally, it is a reminder, to take smaller steps, to keep my legs together while seated, and bend at the knees with my legs together if I have to retrieve something off a lower shelf or from the floor. Finally, my face is powdered, my eyes are made up as are my lips. I am wearing a brunette wig which falls just under my chin softening the sharper angles of my face.

Mistress Sera is dressed in fitted black slacks, a red silky blouse, exposing the cleavage of her heavy breasts. She is not overweight, nor is she thin. She is thick and tall in a way suggesting she was athletic in earlier times. Her hair is jet black and she has striking wide set blue eyes. Mistress is not overtly loud or domineering. But somehow the tone of her voice demands attention. The waiter serving us has scurried around like a puppy dog making sure we are pleased. The glances of the men at the bar, I realize suddenly are not questioning glances. They are the glances attractive women are used to, or otherwise bear up under.

This is the first time I have been presented in public. I was not prepared when Mistress told me we were going out shopping for more clothes and then going for lunch. As I sat at lunch, I was nervous. What if someone saw through my clothing and make-up or recognized me? At the same time I was very aroused, the clothes and butt plug doing their work. My G-string constraint was being put to the test.

"Hasn't this been fun," Mistress commented as we were getting ready to leave the restaurant.

"In-between the periodic feelings of terror, it has been," I agreed.

" You are a funny girl, Angela. Let's go now, before one of those oglers at the bar try to pick you up", she laughingly replied.

Now, the question one can ask is how a perfectly normal middle aged business man arrived at this point. And that is a question I may never really answer.

Chapter 2

I am a heterosexual. I truly like women and never entertained bisexuality or

homosexuality. Perhaps infatuated is a better word than like. I am infatuated with women's faces and bodies. Their scents are intoxicating and their orgasms seem so much more intense than mine. Somewhere in the back of my mind was a desire to know what a woman truly felt day to day or when climaxing. This must have been where it all began. This thought in the back of my mind, turned to desire and then to an itch replete with fantasies. From there it is a small but significant step into Wonderland.

I started by shopping for women's clothes. The lingerie section of a large department store was where I began. First, I picked out a bra which was heavily padded in order to create the appropriate profile. I then selected some with skimpy panties recognizing that a thong wouldn't contain my cock. Panty hose was an option but I thought a garter belt with stockings was sexier and better satisfied my fantasies.

I was quite self-conscious while I was shopping. I convinced myself, however, that the sales women would think I was shopping for my wife or girlfriend. When one of the sales women did ask if she could help, and inquired about sizes, I hesitated in giving an answer. I did not know my size in women's intimate apparel or in regular apparel for that matter. So I fumbled out that my wife was about my size which resulted in a smile and raised eyebrow. I realized at that moment that I may not be the only man that has wandered into the intimate apparel section with an itchy kink. Ostensibly, my purchases were completed without undue attention or questions. I found a pair of low pumps in a discount store where I could discreetly try on shoes off the rack. A lacy, short red, clingy dress was ordered from an on-line store specializing in erotic clothing and accessories.

Back home, I dressed in all that I had bought. This was a bit of a challenge as I have never wrestled with bra and garter belt clips. Looking in the mirror, I felt foolish. I looked like a half made up drag queen masquerading as a French whore. But I, nevertheless, felt mounting excitement which I needed to release. Using some hand cream, and pulling my panties aside, I stroked my erection and climaxed quick and hard completing my first step down the rabbit hole.

I realized soon after my initial shopping excursion I needed more than just dressing up and jerking off; maybe affirmation of my desires or guidance. It's not like you can just go about asking your day to day acquaintances about this sort of thing. This need, this itch naturally led to escort sites. I focused attention on those escorts who mentioned "kink" in their profiles. I also searched on terms like femdom, and dominatrix and was taken-aback. The women pictured on these sites were, as a rule, dressed in ghastly costumes and had scowling faces. Moreover, I wasn't looking to get tied up, whipped, or have my cock and balls tortured or endure similarly cruel ministrations of female dominance. When I happened upon Mistress Sera, my interest level rose significantly. The photo of Mistress showed an attractive woman, looking to be in her mid- thirties. She was smiling in a Mona Lisa sort of way, and was dressed in a white summery dress which highlighted her ample breasts and long legs. Mistress was a woman who if you saw walking down the street or in a cafe on a summer afternoon, you would certainly take notice.

Her message was straight-forward and welcoming. " Tired of plain vanilla encounters," it started. " Be honest and respectful. Tell me your desires and fantasies, and if they are of interest to me, I will respond. Newbies are encouraged."

After fretting for a week if I should email Mistress Sera and going through a number of drafts, I decided to follow Mistress' advice and be honest. I wrote I was a newbie and, didn't really understand the terms of art in representing my desires. In short, I don't know if I am a "sissy" or something else. I have explored, in private, cross- dressing and enjoy the transformation. I do know my desires and fantasies don't encompass corporal punishment. In short, I think I need guidance and therefore I am respectfully requesting a meeting.

The better part of a week went by without a response and I had assumed I was of no interest to Mistress Sera or she didn't really exist. Who knows what is actual on-line? Then, the response came.

"Labels, or terms of art. as you write are for people of limited imagination and intellect," Mistress Sera wrote. "Most newbies who come to me don't know what they want even if they think they do. The people who fulfill their desires, and satisfy me, are open minded and are prepared to follow my lead without hesitation or question. I am available during the day in a private home. "Phone me if you want to schedule a time to meet."

Chapter 3

I had been standing at the door of a neatly kept ranch house on a quiet cul-de-sac for a couple of minutes deciding whether to ring the bell or turn around and drive away. This is crazy I thought. Here I am clutching a small bag of women's clothing and about to enter into a strange women's house and follow her orders. The door suddenly opened and there was Mistress Sera. Mistress was dressed in black leggings and heels and a thin strappy black blouse cut almost halfway down her torso. Her boobs were almost falling out and I could clearly see the outline of her large nipples.

She looked up and down at me quickly, nodded toward the bag in my hand and said, " I need to see what is inside the bag you are holding". I handed the bag to her while not trying to stare at her tits.

She looked inside the bag and while doing this she said, "I heard your car pull in. " If you want to change your mind and leave, then go. If you want to come in, close the door behind you and wait in the living room to your right." With that she turned away and started walking into the house.

I hesitated a moment more, took a deep breath then stepped forward and turned right. The living room was nicely appointed. The front drapes were drawn. The floor plan was open and I could see into the dining area and out through a picture window into a fenced back yard. Beyond the fence there were no visible houses. It appeared that the cul-de-sac backed on to a preserve or parkland. To the left of the dining area was a kitchen and island. Mistress Sera was at the island pouring a glass of what looked like iced tea.

Without looking up, Mistress Sera called out, "I'll be with you in a moment. In the meantime, strip off all your clothes."

I kicked off my loafers and began hesitatingly, to remove my shirt when Mistress Sera came into the living room sipping her iced tea. " Come on now," she said impatiently. " If you were getting ready to fuck, you would be out of your clothes already and stroking your dick."

I fumbled around as quickly as I could removing the rest of my clothes and stood there feeling very exposed which, of course is exactly what Mistress Sera intended.

Mistress circled around with an appraising look. " You have a nice body if you want to be a girl, she murmured, and I assume you do," shooting a glance at the bag I had dropped on to the floor.

"Now," she said as she lightly batted my cock and balls, we will have to do something with all this pubic hair. God, how unsightly, not to mention the hair on your ass." "And look you're already half at attention, she chuckled as she flicked at the end of my dick; how predictable."

She stopped talking suddenly and looked me in the eyes. "Repeat after me, "Code Blue", she commanded.

I did not know the intent of this command but I dutifully repeated "Code Blue".

"Code Blue" is your safe phrase," she said. "Code Blue is what you say if you want to stop doing something, something that is very painful either physically or psychologically." It is not to be used because you are somewhat uncomfortable. Of course, you will be uncomfortable. You're uncomfortable right now."

"Let me be very clear," she continued. "Phrases like Mistress please stop, and no, no Mistress and the like will be ignored. When I hear a pleading no, no, that to me, means, yes, yes."

"Do you understand what I am telling you," she questioned.

"Yes, I do" I replied.

She batted by balls with more authority this time evincing a wince from me. "Perhaps you would like to re-phrase your reply," she questioned once more.

I looked at her raised eyebrow and understood. "Yes, Mistress Sera, I understand, Code Blue, and also how to address you. Thank you for correcting me" I replied softly.

For the first time she smiled, "Now we are getting somewhere," she said with apparent happiness." "I can see already you are going to be a very good girl. Shall we see how you look in the little outfit you brought? I'll help you."

"Yes Mistress," I sheepishly replied, thinking to myself how easily this woman, a stranger a few moments ago had so completely taken control of me.

Chapter 4

Mistress decided to forego shaving my balls and ass, for now. With her help, particularly with the bra and garter clips I was quickly dressed.

Mistress stepped back appraising me. "Well in that skimpy, sheer red dress that barely covers your ass along with the garter belt and stockings you have all the makings of a cum slut," she remarked. "I would prefer you in something a little more classy, but it is a start."

Pulling over a kitchen chair she commanded me to sit. "I'll be back in just a sec, she called as she walked down a hallway towards where I assumed there was a bathroom and bedrooms.

She returned with make - up cases and two wigs. She started in on the make-up and then considered the two wigs, settling on a brunette wig with straight hair which came just below chin level.

" Not bad, not bad at all," Mistress chuckled. "Let's take a look."

She led me down the hallway into a bedroom where there was a full length mirror. I startled myself when I looked at my reflection. With the wig, and make-up, I hardly recognized myself and I most certainly felt different.

"I can see on your face you are, how shall I say this; adopting your new persona," she purred close to my ear. "Now, when you sit, keep you legs together. Even sluts don't let their twats hang out. Oh, and we do need a name. Let's settle on Angela. You look like an Angela to me."

At that moment the doorbell rang and I saw Mistress look towards a clock on the nightstand.

"My goodness," she exclaimed. "I lost track of the time, come with me."

I followed Mistress back to the living room where she held up her hand and said "wait here."

She proceeded to the door and I could hear the voice of another woman. The voice had a slight Island accent. Soon, I heard the door close and Mistress returned to the living room with a buxom, large hipped ebony women with the face of an angel.

" Darla, meet Angela," Mistress said as if it were a normal introduction. I was mortified. I was not prepared to be displayed to a stranger. But wasn't Mistress a stranger? I thought for a moment about using Code Blue and then, just stood there wordlessly.

"Well, what do you think," Mistress asked Darla.

"I think she is a little skinny, but she is cute. Is she well behaved," Darla questioned in her lilting Island accent.

"Let's see", Mistress replied.

"Angela dear first close your mouth, it is unappealing," Mistress instructed. " Darla is a good friend. She is somewhat new to all of this," Mistress said, waving her arm towards me.

"Turn around please and lift up the hem of your dress so Darla can see all of your cute butt," Mistress ordered.

I did as told.

"Bend over a bit and wiggle your ass so we can have a full appreciation," Mistress commanded again.

Again, I did as told to the giggles of the two women. Yet through this performance I could feel the swelling in my cock. I was mortified and aroused at the same time.

"Is she a virgin," Darla inquired.

"Hmm, I haven't fucked her. Angela, have you fucked," Mistress asked casually.

"Well, yes I replied, I have had sex, with women."

"No, no," Mistress responded as she walked towards me. you misunderstand." She bent me forward again and pulled up the hem of the dress and gave my ass a firm slap. She asked again, "have you ever had your pussy fucked by a woman or a man?"

The look on my face betrayed the answer and both women laughed. Darla exclaimed, "Angela, there is a first time for everything."

Mistress Sera then walked behind Darla and cupped her ample breasts with her hands. "Don't you wished you had boobies like these," she questioned.

With that she unbuttoned the house dress that Darla was wearing. As Darla slipped her arms out, the dress fell to the floor. Underneath Darla had on only a bra and skimpy lace panties. Her breasts were overflowing the bra and Mistress Sera reached in and underneath Darla's breasts and unleashed what were truly a magnificent set of tits adorned with oversized areolae. Instantly, my dick reacted and hardened.

Mistress then came in front of Darla and started sucking and massaging Darla's breasts.

Darla moaned, "oh Sera, that feels so nice. My pussy juices are starting to flow now!"

"Let's take a look" Mistress replied, and pulled Darla's panties down to her ankles. She resumed sucking Darla's breasts as one hand dropped between her legs and found Darla's clitoris.

Darla reacted with an "oh yeah, Jesus, that feels good." I reacted also with my dick now straining at my panties which would be clearly noticeable.

Mistress started walking Darla towards the chair that she had pulled into the living room as Darla kicked off her panties.

"Now Darla hon", bend over and put your arms on the chair seat," Mistress lightly commanded.

"Real nice, wonderful," Mistress continued talking to herself as she gazed at Darla's ass.

"Angela, come over here and Darla spread those legs wider, yes that's good," Mistress said in a matter of fact manner, as if we were in a Doctor's office.

"Angela I want you to kneel, spread those butt cheeks wide and get busy with your tongue," Mistress commanded more forcefully. "I want you to rim Darla and you certainly look like you are in the mood," and she grabbed hold of my protruding dick." "You'll both enjoy it," she laughed. I'll come back in a minute or two."

When Mistress returned my face was being smothered by Darla's large undulating ass. Though muffled I heard her moaning and speaking in a language that sounded like French.

" Are we all having fun now," Mistress exclaimed. " Darla, turn around and have a seat at the edge of the chair."

Remaining in a kneeling position, I extricated myself from Darla's rear end as she re-positioned herself. Mistress was now holding a flesh colored dildo in a harness.

"Oh my" Mistress chuckled, you are really dripping now". She said this as she rubbed the dildo on and then in Darla's pussy. "I think you deserve a big orgasm, don't you agree Angela," Mistress asked.

"Yes Mistress," I dutifully replied.

Mistress then stepped into and fastened the harness around her thighs and legs and pushed the dildo onto my lips.

"Be a good girl and clean Darla's pussy juice up for me" Mistress commanded.

I hesitated and again the look on my face surely gave away my trepidation.

"Oh, come on now. It isn't real and a slutty little girl like you has to try sucking cock sooner or later. If you are good, maybe we will let you cum later, so grab on to the base with your hand and grab on with your lips and tongue," Mistress instructed.

I really didn't have much of a choice as she thrust the dildo into my mouth and started slowly thrusting her hips. As her hips moved forward I almost gagged on the dildo and I could hear both women giggling.

After a few minutes, Mistress withdrew the dildo and told me to get on all fours.

"Now Ms. Angela, get that tongue working again on Darla's twat and give her that orgasm you agreed to," Mistress commanded.

As I began licking Darla I could hear Mistress behind me. "What a sight to behold, what a sight," Mistress stated with satisfaction.

I then felt the hem of my short dress pulled up and my legs pushed wider. A moment later I felt the skimpy panties I was wearing pushed aside and something oily being applied to my pussy. And then, I felt the penetration.

Mistress's voice was purring, "relax Angela, you feel my finger, just relax." The finger penetrated deeper and the initial discomfort abated as I felt Mistress's finger gently move back and forth all the while purring "relax, relax and enjoy the feeling." Then the finger was withdrawn, and I felt more pressure and more discomfort bordering on pain. Again, after initial penetration the pain abated and I felt what I then realized was the dildo gently moving back and forth.