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My ass hurt the entire next day from Ms. Ward’s strap on. I was red-faced most of the day imaging the other guys at work knew why I was walking a bit delicately. I made it through the day without comments though.
I thought of Renee constantly. Longing to see and touch her again.
I received a call on my cell phone that Wednesday from Ms. Ward. She had evidently gotten the number off my phone that had been in my swimsuit on Sunday.
Ms. Ward reminded me to be at her place at 7:00 PM that Friday. She again reminded me that I would be spending the weekend. I naively asked her what kind of clothing I should bring. She told me my toothbrush. She also told me I was not to jerk-off or cum for the remainder of the week.
The week flew and dragged by. I was anxious to return and scared as hell at what I was getting into. I kept remembering Renee and my love for her.
Friday came and I made up an excuse with my parents that I’d be gone for the weekend.
The curse of Italian parents is they want to keep track of you, even when you’re an adult. At 18, I felt I could take care of myself, but with Ms. Ward, I certainly had some doubts.
I arrived back at the penthouse at 6:55 PM. I was determined to not be late.
I had caught a glimpse of the security guard who had cuffed me last Sunday as I entered the building. He gave me a dirty look, but said nothing as I entered the elevator.
Ms. Ward answered the door after my ringing the bell.
She again looked beautiful wearing a blue dress with a plunging neck line and a short hemline. Her breasts seemed to be struggling to stay in there. After picking up my jaw and pushing my eyes back in their sockets, I noticed there was no visible tan lines on her. Just one solid bronze color.
Ms. Ward ordered me inside, in that quiet, powerful voice of hers. Upon closing the door,, she ordered me to strip there at the fores’. I hesitated but a minute. Ms. Ward stated if I was not ready to follow her orders immediately and without question, I could leave now.
At that moment Renee made her appearance from the back room. She wore a lace, halter top that showed her magnificent breasts through the loops of the lacing. She was not as large as Ms. Ward, but her breasts stood out firmly against the material. She also wore a wrap around skirt that seemed a tad short as her leg was revealed to the belt at her waist with each step.
Her smile again struck me with awe and I immediately decided anything Ms. Ward had to dish out I would endure to be with Renee.
I quickly removed my clothing and stood before them naked. Ms. Ward ordered me to interlock my fingers behind my head and spread my feet shoulder length apart. She then began an inspection of my body, slowly circling me.
I felt Ms. Ward’s hand against the inside of my thigh. Her hand was warm and softly gripped my leg as she moved around behind me. I then felt one hand pushing my back forwards as her other hand gripped my ass cheek.
I bent at the waist until I felt the pressure from her hand ease. I then felt her fingernails rub lightly over my asshole and push gently inwards. She did not enter me, but the sensations were driving me crazy having not cum for a week.
Her hand then lightly cupped my balls and pulled them back. She released then and grazed my sac with just her fingernails. I closed my eyes at the exquisite feelings she was creating. My dick was quickly hardening at her inspection and touching.
Ms. Ward told me to straighten back up as she continued moving back in front of me. She then lightly grabbed my cock and began to lightly stroke me. She would gently rub her thumb around the underside of the head my erect penis, making my knees quake. I actual began to pant from her ministrations. She would dab her finger into the pre-cum leaking from the tip and smear it over my dickhead. As soon as she felt my hips jerk she pulled her hand away and swatted my ass with her other hand.
I was in agony thinking of how badly I wanted and needed to get off.
Ms. Ward then looked to Renee and told her, “I want him shaved and cleaned out. He’s not to cum. Do you understand me slut?”
“Yes Mistress.” Renee quietly answered.
Turning to me, she told me to follow Renee, adding “Don’t cum or there will be Hell to pay.”
I followed Renee back to a bathroom. Upon entering the room she turned and melted into my arms. I grabbed her and pulled her too me with both my hands on her ass. Our lips met and everything seemed perfect. Her tongue entered my mouth and I pushed back with mine. We stayed locked like this forever, yet not long enough. She released me with a moan and said we needed to get started.
I was confused as Renee told me to sit on the counter top with my legs spread wide. She reached under the sink and brought out shaving cream, scissors, and opened a new razor.
Renee began cutting my pubic hair until it was nubs. She then lathered the remaining hair and began shaving me with slow, careful strokes.
Having the woman of Cihangir travesti my dreams so close to my groin was driving me crazy. She would occasionally get a dirty little smile on her face and lick the pre-cum from the tip of my dick making me groan. She had definitely learned her Aunt’s methods of teasing.
She continued until my front and balls were as smooth as the day as I was born. She then had me turn and bend over, shaving any of the fine blond hairs around my asshole and cheeks.
Renee gave a quick kiss and lick to my asshole after wiping the remaining shaving cream off.
Renee then removed what I recognized as an enema bag from below the counter. She told me she would make it as comfortable as possible, but.
Renee filled the bag with warm water and added a touch of some scented soap. She then told me to get down on the bathroom floor, resting my upper body on my arms and ass in the air. I was deeply embarrassed and red faced as I complied.
Renee had lubed the nozzle end and began busing the stem into my ass. The stem was small and slid in. I then felt a bulge and Renee quickly massaged my balls and told me to relax. I did the best I could and felt the bulge move past my sphincter muscle, filling me like never before. “Okay, here we go my love.” I then felt the warm water entering me.
It seem like she poured a gallon of water into me as I felt my bowels cramping and feeling bloated. I’ll for ever have empathy for pregnant women as I felt my stomach begin to distend and the water kept going.
Finally, Renee told me that was all and I felt a slight tug as she disconnected the bag from the stem and bulb in my ass.
Renee had me stay in this position for several minutes, then told me to be ready to hop on the commode. I felt her pull the bulb out and the urge to let the water rush out of me was tremendous. I immediately jumped on the toilet and felt like cumming just from the relief of the water rushing out of me.
After what seemed like ten minutes, the flow stopped. I was embarrassed and humiliated as I thought of going through all this with Renee right there. She seemed unconcerned and unabashedly grabbed some toilet paper, reached between my legs and began sopping up any remnants.
She then told me we needed to repeat this process until I was clean. I groaned but resumed my position on the floor for two more bouts. After the third time Renee told me that was it.
She wiped me down with a damp cloth, then had me bend again and gently pushed some lubricant into my ass with her finger. She began sawing her finger in and out of me until my hips began swaying and I tried to push back against her finger. She laughed and gave me a light swat on the ass, telling me to stop.
I then rose and our lips locked again. “God, I so want you” she told me as she reached between us and slowly stroked my hard prick.
I reached through the slit of her dress and felt a tight pair of thong underwear. I then found her hard cock was pushed rightly back towards her asshole. I began to stroke her and could feel her begin to move her hips in rhythm to my rubbing.
Renee was flushed as she pushed back away again saying, “I’m sorry, I’m so sorry. You can’t come or Mistress will be very mad.” I groaned and decided to go see what else Ms. Ward had in store for me.
We walked out of the bathroom hand and hand to the waiting Ms. Ward. She had a slight smile on her lips seeing us, but that quickly disappeared.
There are some clothes sitting on the bed in the back bedroom. Go put them on and come back out here quickly so we won’t be late.
I found a pair of very short cut off jeans sitting on the bed, but no underwear. I pulled them on and noticed the sides of each leg had been split to the waistband. I was worried about keeping everything inside the shorts while not wearing any underwear, but, no guts no glory.
The only other piece of clothing was a black, mesh shirt that was a tight fit. The holes of the shirt aligned perfectly to allow my nipples to poke through. The holes seemed to grip and tug my nipples when I moved, sending little jolts of pleasure straight to my groin.
I never appreciated how sensitive and erotic my nipples could be until I felt that shirt on me.
The shirt stopped short of the pants, leaving my midsection exposed. I have a slim build and a six pack from working out in karate, so I wasn’t to concerned about the exposure.
Ms. Ward had also purchased a pair of strap sandals for me, which appeared to fit perfectly.
I happened to look in a mirror in the bedroom and saw the picture of a male slut standing before me. My vanity jumped in and I felt a twitch in my cock from the sight. I so wanted to reach into my shorts and stroke myself, but I remembered Renee’s and Ms. Ward’s warnings. With a growl, I walked back out to the front room.
“Perfect” Ms. Ward said as she looked me over. Renee looked ready to pounce on me right there.
Renee was now wearing a pair of 3″ stiletto heels, Fındıkzade travesti raising her up to 6′ tall. At 6’3″, I’d never met a woman that could almost look me in the eye. The shoes accented her calf’s and added a grace to her movements. Oh crap, there goes my cock out the bottom of my shorts.
Ms. Ward picked up the telephone and simply stated’ “ready.” She then led us out of the apartment to the elevator. We rode the elevator to the garage where a Mercedes was waiting for us.
Ms. Ward’s driver was in a full chauffer uniform. She stood 6′ tall and filled her uniform well. She appeared to have large breasts to match her build. I doubted there was any fat on her from the lithe way she moved. I subconsciously gauged her on how I’d do if I had to tangle with her. I wasn’t to sure I’d win.
We entered the back seat with Renee first, myself, and lastly Ms. Ward.
The driver quietly went to her side and we began to drive out of the garage. Our destination must have been prearranged as Ms. Ward made no comment of directions and the driver did not ask.
Ms. Ward then began asking about my work, education and plans as if it was ordinary for me to be sitting between to beautiful women, worrying about getting excited and having my cock poke out the bottom of my skimpy shorts.
I actually began to enjoy Ms. Ward’s company as we rode. She was an excellent listener and seemed genuinely interested in me. I briefly forgot that this same woman had fucked me with her strap on the week before.
I had hoped we were going to some place quiet as I was sure I’d die of embarrassment if I was seen in public dressed as I was.
“We’re here Ms. Ward announced as we pulled in front of a very expensive looking restaurant in the middle of the elite shopping area of Palm Beach. The car pulled to the curb and the valet quickly opened Ms. Ward’s door.
Ms. Ward gracefully exited the car with an air of confidence and elegance that spoke volumes of who was in charge. I followed as quickly as I could trying my best to keep some modesty and failing miserably.
The flaps of my short had ridden back as I slid across the seat. My right rear was almost completely exposed as I stood and quickly pushed the shorts back down.
Ms. Ward loudly stated, ” Cover yourself slut, you don’t need to be showing everyone everything you have.”
She looked at the valet chuckling and said ” I need a leash on the little cock whore. He always wants to show himself off.”
I looked quickly towards the valet and noted a smirk on his face. If I could have found a hole I would have jumped into it to hide my utter embarrassment. Maybe it was from not cumming all week, but I always felt a twitch in my cock.
He then offered Renee a hand as she exited the vehicle. I felt a touch of jealousy as I saw how attentively the valet was staring at her. I made a move towards Renee but was cut off with Ms. Ward telling us to go inside. I felt Renee crook her arm in mine as we entered the restaurant, following Ms. Ward.
“Hello Bruce, how are you?” Ms. Ward said to the maitre’d. “Ms. Ward, a pleasure as always.”
“Your usual table?”
The restaurant was somewhat dimly lit and I hoped Ms. Ward’s usual table was not too deep into the restaurant.
No such luck. We wound up being led through the tables to one in the back that was apart from the rest.
I was unable to look at the other diners as I felt every eye in the place could see all I had as the sides of the shorts slightly flapped opened as I walked. I was red faced and warm by the time we were able to sit in our seats around the table.
Ms. Ward made sure I was in the center of her and Renee.
The waiter was immediately at our table greeting Ms. Ward, Renee and I equally, but immediately turning his attention to Ms. Ward.
Ms. Ward ordered a bottle of red wine and the waiter immediately left.
We were each poured a glass of wine with no questions asked regarding ages or ids. I quickly surmised Ms. Ward carried some weight to her. It was obvious she was not hurting for money from the penthouse, chauffeured Mercedes, and being greeted as a regular here. I really felt I was in over my head coming from a lower middle class family.
Ms. Ward ordered for us with out asking. The waiter made no comment to the control Ms. Ward showed over Renee and I. He again left with our order.
Ms. Ward again engaged me in conversation while Renee sat quietly beside me holding my hand. The meal was delicious and uneventful other then Renee or Ms. Ward occasionally rubbing my thigh and pushing my shorts up. I felt hidden by the table cloth and just enjoyed the erotic feelings and “naughtiness” of being almost naked in the restaurant.
I was beginning to think that if this was the way Ms. Ward wanted to control me, I would be more then happy to be spoiled to death. But, she of course had other plans.
Towards the end of the meal, Ms. Ward leaned towards me and spoke quietly into my ear.
“I Fulya travesti will be paying for dinner, but you will provide the tip,” You will thank the waiter and tell him you will provide him with “anything” to thank him. If he’s hesitant you will beg to be used by him.
” Do you understand.”
Her tone left no room for discussion. I felt the blood rush to my face and broke out in a light sweat thinking about what I would have to do.
I had never had another sexual experience with another man. Yes. I had sucked off Renee the week before, but some how that just did not equate to having openly gay sex with another man.
The waiter returned with the bill and I felt a nudge under the table from Ms. Ward.
I looked towards the waiter and worked up my courage.
“Excuse me”, I said.
“Well, I’d like to thank you “personally” for your attention and service during our meal I stuttered out.”
“That’s not necessary, it was my pleasure.”
Great, I now understood why a stupid deer stops in the middle of the road when car headlights hit them instead of moving out of the way. I had no idea how to look sexy for another guy, and the waiter wasn’t catching my pitches.
“No, really, I want to thank you, anyway you’d like.” Emphasizing the last words by licking my lips.
Well, he was a bit smarter then the deer it turned out. He got a wry look and told me to watch him as he went back towards the rear of the restaurant and the bathrooms.
“I’ll give you a nod, and walk to the back. You follow me.” He then walked off.
My knees were shaking and hands sweaty as I thought about what I was about to do. I also felt my nipples pushing their way through the meshing of my shirt and my cock starting to harden.
I then saw the waiter standing by the back. He gave a quick nod then walked back towards the bathrooms.
“Don’t embarrass me slut. Make sure you clean him up, no matter what”, Ms. Ward said as I pushed my way out past Renee. We kissed quickly as I moved past her.
I felt like everyone in the place was watching me and thinking, “There goes a cock sucker for his treat.”
I thought the waiter had entered the bathroom. As I began to push on the door to the men’s room I heard him call me from further down the hall and pointed towards a small office door.
The waiter, Paul, immediately pushed me against the door and began an open mouth kiss.
“We have to hurry, I don’t have much time.” He said.
I was contemplating the difference of the roughness of his lips pressed against mine as he kissed me. His hands had slid under my shorts and grabbed my bare ass. My cock was now hard and poking out from the bottom of my shorts.
Paul was a black man, in his late twenties or early thirties. He stood about 5’10” and weighed about 180 pounds. He had a moustache, which added to the differences I was feeling while kissing him.
Paul moved back and told me to lose the shorts. I unbuttoned them and they slid easily off me. Paul rubbed my hairless crotch telling me what a horny little cock slut I was. He then unbuckled his belt and pulled his pants and underwear down.
I looked at his cock and realized, damn, maybe those stories are true. Paul had a dick about 9″ long and standing at attention.
Paul pushed me down to my knees and said “Come on bitch.” Get your slut mouth on me and thank me like a proper cock sucking slut. I wanted to explain to him I wasn’t a cock sucker but thought about Ms. Ward’s warning.
I began to stroke Paul’s cock with my hand. I was entranced by being so close to another man’s stiff cock. Especially one this big. I felt a smack to my head as Paul said “Come on bitch. I’m not here for a hand job and I don’t have all night. Get that pussy mouth of yours on me.”
I leaned forwards ands enveloped Paul’s cock in my mouth. I began licking and sucking him trying my best to please him. It must have been working as I felt him grow slightly larger in my mouth. Paul then begin fucking my mouth by placing his hands on the back of my head and pushing me forwards onto his cock.
I was unable to take his full length down my throat and gagged several times as Paul tried to push himself into me.
“Please sir, I’m really new at this and can’t take all of you”
“Well fuck, that’s just great.”
“All right, you said you’d thank me anyway I wanted, so get up, turn around and bend over.”
I was really scared now. I was about to be fucked by another man. Ms. Ward’s strap on was one thing, but this is way beyond anything I’d imagined.
I then pictured Renee and losing her if I didn’t perform to Ms. Ward’s satisfaction. I had no doubt she had known this was a possibility and worried that she would check with Paul.
I did as Paul said and sounded girlish to myself as I told Paul. “please be patient. I’ve never done this before.”
“You mean your ass is cherry?” he asked incredulously.
“All right my little faggot baby. I’ll treat you like the virgin slut your telling me you are.”
Paul then pushed one of his fingers into my asshole. He quickly discovered the lubricant and said “I thought so slut. Your just fuckin’ with me. No virgin would be all greased up and ready to go if you weren’t already a pole rider.”
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