I consider myself not a bad looking guy, with full dark brown hair and about 5′ 10″ tall. I’m lean from all the triathlon training and obviously fit. I have no trouble conversing with the ladies and have a few female friends, both at work and at the Triathlon club. But because of my daytime job and triathlon training I have never found time to fit in a relationship or find the right girl. Perhaps it’s also because I’m a little kinky and the girl I’m looking for is not easy to find.
That’s why I occasionally fork out the money for a well spend private session with my private ‘masseuse’. I found her website one day by accident when a popup advertising local escorts came up on my screen, and I don’t usually surf the porn sites. I was about the quickly close the popup window as usual when I noticed this one lovely lady on the list catered specifically to my little kink. Cautiously I clicked on the link and clicked on the particular escorts’ link when the web page loaded.
Her website was very tastefully and had rolling images of her in various outfits, but none showed her face. Her long soft looking hair covered her face in every photo.
Her advertisement read:
I am a gorgeous, tiny, super busty blonde with the easiest going, open-minded personality you will ever meet.
I also guarantee that no-one else in this business can do greek like Jennifer can;
That’s why I dominate the industry (specializing in greek). I’m 5′ 2″ 100 lbs. (34D-22-32) with long blonde hair & tanned.
Monday to Friday
12:30 pm to 6:00 pm.
I called her number from my call display blocked cell phone and the sweetest voice answered. Not having ever done this before I hesitated before I spoke.
Stumbling, I said, “Hi. I saw your website and was interested in meeting you. But I never done this before and don’t quite know how to proceed.”
“That’s ok, hon. I’m very patient and caring. What was it about my ad that interested you?” Her soothing voice made me feel so at ease.
“I’m interested in greek, but…and other small kinks, like rubberwear lingerie. I guess I should ask how much you charge?” I hesitated.
“I’m very open minded and enjoy most non-violent kinks. My rates are $210 per hour, or $160 for a half hour.”
“Yikes!” I thought to myself, “Those are pretty steep prices.”
“Can I think about it and maybe call you back?” I asked.
“Sure, hon. If you think those prices are expensive I can save you the time of checking around and guarantee you that no one does what I do and in the caring way I look after my clients. My prices are about average, if you can find any other girls like me.”
“Ok, thanks. I’ll get back to you.” We disconnected and I pondered the whole idea. I had never even considered paying for sex, let alone that much money. I mean I could blow over $200 on a golf game, or a day of skiing, but this was only one hour.
For a whole week I pondered the idea, or rather my dick pondered the idea for me. I grew hornier and more restless as the week wore on. Thinking, dreaming, fantasying about fulfilling my fantasy, especially with a beautiful girl like her pictures advertised, kept me awake at night. I considered that maybe she had a paper bag ugly face, but then rationalized that by charging that much money it couldn’t be possible she was fugly.
After a very long, erect, weekend I broke down and called her.
“Hi Jennifer. I called last week to ask if I could see you.”
“Hi,” she purred, “I remember. You said that you are new to this and a little kinky.” I couldn’t believe she remembered me.
“Would you like to get together today?” she asked.
“Yeah, I’d love to.” I said. “Was I really going to do this?” I thought.
“How about 2:00 today? Did you want a half hour or an hour?” she inquired softly.
I had finished my sales calls for the day, and after all, the business was already at capacity and not taking any new jobs.
“Yeah, 2:00 is great, for an hour.” “Why not get the deal in per minute cost averaging?” I laughed at myself.
She gave me the address and details and said sweetly, “I’m looking forward to meeting you. What’s your name?”
“Jack,” I replied honestly.
“Ok Jack. See you soon.”
I went home and prepared then drove to her place, which was not too far away.
I knocked at her door and what I saw took my breath away. She was drop dead gorgeous. Her fit, slim frame was adorned with a tasteful white see through negligee under which she wore white stockings, garter belt, and a delicately patterned white bra embracing two beautiful 34D breasts. Her face was angelic and had the most beautiful smile. She looked me up and down in my tailored blue suit with my sales tie and said,
“Oh my, you look handsome.”
“I bet you say that to all the guys,” I replied sheepishly.
“Actually… no. I don’t. Not many of my customers are as attractive as you.” She said candidly.
I must have blushed, but at the same time I remembered where I was, especially after she mentioned the word “customers.”
Isn’t it silly how we think we can block out aspects of an undesirable situation, like paying for sex.
None the less I was here, and she was mouth watering. She ushered me in to a very tastefully appointed apartment with a forth floor view over looking the river. The furniture, pillows, and prints on the wall looked like an interior decorator had spent some time here, and quite a few dollars.
“Very nice place,” I remarked as I gazed around.
“Thanks, I did it myself, even sewed the drapes and cushions. I’m taking courses at the college to get into interior design.”
“I think you will do well,” I offered.
“Thanks. Well, how about we get you comfortable. Why don’t you take off that jacket and tie and we’ll have a quick chat.”
She put me right and ease and took care of business as she discreetly took my money and put it away. During our talk, I found myself admitting my kinks to her as if it were everyday conversation. I had never admitted these things to anyone, yet she made me feel like all my kinks were perfectly normal.
She admitted that she had the same desires and couldn’t wait to explore them with me.
“Why don’t you make yourself comfortable in the bathroom and join me in the bedroom when you are ready. Or would you prefer that I undress you?”
“I would love to see you wearing what we talked about then have you undress me. I’m still a little tiny bit shy and unsure of all this. And I took the time at home to get prepared before I came here.”
“That’s perfectly understandable. Don’t be at all concerned about being shy. But I just want you to be comfortable, and remember, we both have the same kinky side,” she hugged me tenderly and erotically at the same time. “Come and help me change if you like,” as she took my hand gently and guided me into the bedroom.
The decor in the bedroom matched the tasteful design in the rest of the seemingly spacious apartment. The air smelled fresh and cool air in the air conditioned room. A large king size bed sat angled in the corner opposite the window while she opened an antiqued entertainment cabinet opposite to turn on a softly playing anal porn movie. “Is this all right? It might help to get you in the mood and show how open minded I really am.” The video showed a couple on the screen engaging in a soft glow what we were about to perform.
“Perfect,” I said, “but honestly you are so beautiful and making me very aroused already.”
“That’s so sweet. Thank-you,” She beamed. “Now come and help me get dressed. I have a great assortment of latex and I want you to pick out what you would like us to wear.”
The next ten minutes were almost uncontrollable bliss. Her collection in the walk in closet was vast and the heady smell of a wide variety of clean latex hung in front of my fingers. I picked out a black nippleless bra for her with matching black elbow length gloves and black panties with a five inch dong for her pussy fitted to the inside of them. To complete the outfit I offered the thigh high latex stocking hanging by delicate clips. For me, she suggested a black halter and brief combination with the briefs sporting a hole for my raging hard-on. She also suggested a black latex cock and ball sheath which she pulled out of the top drawer of a mahogany armoire. We giggled as we each gratefully accepted each others choices and looked lustfully into each others eyes. “This is going to be so much fun,” she said as she squeezed my arm. All I could do was smile like an idiot.
I helped her remove her bra, lace panties, and garter belt and stockings, running my fingers over the silky material as I did so. Her all natural breasts barely sagged as I gently removed her bra, taking care to brush my fingers down the sides of her ever so soft breasts. She sighed as I did so and her breath heaved in anticipation. Quickly, anxiously, we redressed her in her new shiny black outfit. She adjusted her nipples so they bulged out of the nippleless bra and I yearned to suck them into my mouth. She read my thought and cautioned me to wait, holding the anticipation. She pulled up the latex gloves, snapping them above her elbows. As she lifted her feet to accept the cocked panties and I slid them delicately up her toned legs. She touched my hand to pause me from moving them up further. She winked at me and reached back to the dresser to squirt a portion of astroglide in her left hand. She rubbed her lubricated hand on her shaved pussy and reached back to her puckered star as well.
“Let me feel both holes full and excited,” she breathed. She reached into the second drawer and extracted a fleshy medium sized ribbed butt plug. “Do you mind if I fill myself?”
“Hell no. That is so right. Can I help you?” I excitedly asked.
She nodded seductively and handed me the butt plug as she began to turn around and bend over.
“What a perfect lubricated asshole,” I thought as I gently, slowly screwed the plug into her expanding anus. She took it with ease, with a satisfied moan as it seated itself up to its second ring in her tight little sphincter. She turned around and I crouched down and continued to slide the loaded panties up her thighs. I gazed lustfully at her moist pussy lips as she guided the black latex dildo in it, along side the butt plug as I slid the panties over her hips. Her “Mmmmm” caressed my ears as we completed the panties fitting. She bent over again to reach for the latex leggings and as she did so the third ring of the butt plug seated itself in her lubricated asshole. She shuddered, and giggled and smiled as we completed her outfit. She squirmed with the double penetrations and squishy lubricant massaging her openings.
“Now your turn,” she grasped at me.
“I’m already lubricated and plugged, so no laughing at me now,” I admitted.
Her shock was quickly replaced by shear lust as she breathlessly whispered, “Show me. Quickly.”
She practically ripped the buttons from my shirt as she undid them then furiously grabbed at my belt and fly to expose my white pantyhose encased legs and plugged ass. Lustfully, she grabbed my hips and spun me around to peak at my plugged, lubricated, leaking ass. I did not have any underpants on, just the shear white hose. The kind with no cotton lined gusset, only a thin seem from front to back. The seam forcefully pushed the medium sized rippled butt plug up my ass with every movement. Especially when I sat down.
“Why didn’t you tell me? That is so fucking hot!” she exclaimed. She grasped the base of the plug and slid it out, then back into me slowly, randily. I gasped as she impaled me gently.
“That feels so fucking good. Let’s get me all costumed up in latex. I can’t wait.” I sighed heavily.
She grasped the hips of the nylons and forcefully tugged them down my legs. The butt plug slid out of my used asshole and she caught it in her hands. “You have done this before, nice and cleaned out too, I see,” she lustfully exclaimed.
“Yeah, just fill me up again, quickly,” I gasped.
I lifted my feet, one at a time, as she pulled the latex shorts up my legs, pausing at my thighs.
“Now the cock and ball latex sheath,” as she lubed my engorged six inch, pulsing cock with lubricant from her pump bottle and smeared it all over my cock and trimmed balls, her hand copiously massaging my swollen balls. “So hard and delicious,” she panted, and then slid the tight black latex sheath over my rigid member. Next she pulled two fingers from each hand into the ball sheath and stretched it over my sack, catching my engorged balls in the slick ball sack. Unable to resist she swallowed my full length into her mouth, and sucked tightly. It took all my strength to keep from exploding right then and there. I pushed her head off gently and gasped,
“Fill my ass first.”
She smiled devilishly and reached for a larger, vibrating butt plug from her dresser.
“How about this one?” she grinned at me.
“Oh yeah. Fill my ass with that monster. I can take it. I think.” I had a collection of dildos, butt plugs, and vibrators of my own, which I frequently violated my expanding asshole with. But the largest I had ever taken was an eight inch by two and a half inch ribbed dildo, but only about three inches in, barely past my prostrate. This vibrating plug she was holding was almost three inches around.
“Let’s try. I really want to stretch your ass before I fuck it,” she gasped in my ear.
I was so horny by her dirty talk that I new this would break new limits for me. This was a first for me. Someone who was willing to indulge in my deepest fantasies. I had longed to find someone as perverted as this.
She wrestled the first part in my well stretched and lubricated ass then pulled the latex shorts up over my bottom, snug against the impaling butt plug. She pulled it taught up over my hips, synching the plug further up into my ass.
“Now the halter. Are your nipples sensitive too?”
“Ah huh” was all I could manage as she turned on the remote controlled vibrator and pushed gently the base of my butt plug. She gyrated seductively as the dual plugs inside her ass and pussy massaged her insides. She moaned constantly as she pulled the latex halter over my head and arms then gave a firm tug and twist on my protruding nipples with her teeth.
Next lay the most erotic part – the task of rubbing shiny lube on the latex. She reached for the spray on the top shelf, causing her to convulse involuntarily from her intrusions. After spraying my halter top then shorts and cock sheath she handed the spray to me then rubbed the moisturizer onto my rubber encasement. It felt like a thousand erotic hands rubbing my soul as she smoothed the greasing stuff over my rubber sheathed body. I took my turn at spraying her latex. My fingers caressed her covered body, pausing to delicately slide my fingers around her protruding, enflamed nipples. I massaged my hands down her encased ass and pushed the plug into her. We were both moaning and groaning by this stage and ready for some serious carnal action. I had truly discovered a true soul mate in anal attention with Jennifer. None of the professional, client relationship mattered at this point.
We moved to the bed, our bodies entwined and writhing together. As our hands caressed each others latex hugging bodies we lustfully gazed at each other. We each felt the near electric shocks as rubber touched rubber. The afternoon sun shone through the diaphanous sheer curtains and highlighted the shiny material we both wore.
“Tell me your fantasy Jennifer,” I gazed into her eyes.
“Oh God, this is so good,” she breathed, “Really? No one has ever asked me before.”
“Tell me,” I moaned.
“I’m so full, but I want more. I want you to fill my ass with your cock while I pack my cunt with the largest vibrator I have. Just stretch me.”
“I want to make you orgasm like never before,” I exclaimed, “and then for you to pummel my ass with your big strap-on.”
“Oh, yes, fuck me full. Then I want to fuck your tight little ass!”
We pushed and pulled at each others butt plugs, forcing animalistic screams from each other, penetrating and exciting nerve endings we never thought we had. Jennifer turned on my vibrating butt plug to full power and satisfyingly shoved the three inch wide plug into my grasping ass. My sphincter grasped at it and accepted it fully inside me. The temperature instantly jumped ten degrees as my body strained to take the intruder.
“Aghhhh. Fill my ass, fuck my ass,” I screamed. She changed the vibration speed without any pattern, holding me in suspense for the next high.
“Pull my nipples, suck them deep into your hot mouth,” she screamed back.
For what seemed like hours we continued our anal assault on each other.
Finally, I could not contain myself any longer. The intense tinglings rippled through my body and my orgasm burst out of me into the latex sheath. Through clenched teeth I yelled”I’m cumming!”
“YES! Cum with that plug deep in your ass!” she exclaimed
“Agghhhhhh!” I exploded with a weeks worth of cum into the tight latex sheath.
“Quick, let me rub your cum on me.”
She yanking down my shorts, the still vibrating plug nearly shot out off my ass. I reached back to hold it in me while she pulled her fingers into the ball sheath peeled it off of my soaked balls and still mostly hard cock. Like a toothpaste tube she squeezed the loaded sheath onto her nipples and pinched them with my lubricant. She writhed on the bed, the butt plug and dildo rubbing together in her holes.
“Suck my nipples into your mouth, deep,” she groaned.
I had never tasted my own cum, but I was so turned on and wanting to see her cum like a freight train that I didn’t care.
I sucked one slippery nipple deeply into my mouth while I tried to twist and pull the other one. With my free hand I reached under her and plunged the butt plug out and back into her tight ass. Her breathing went shallow, and then stopped as her orgasm approached. I pulled and sucked more forcefully on her nipples as her body quaked in ecstasy.
“Oh my God, Jack! Oh Fuck, yes, yes. I’m cumming. Yes!”
I held her till she went still, basking in our warmth.
When she recovered she looked into my eyes and said, “That was amazing, I haven’t come like that in years. I want more.”
“Isn’t my time almost up?” I inquired, slapping myself mentally at the same time. I let my big plug slide from my ass into my hand and lay it on a tissue on the bedside table. Her plugs still filled her orifices and she shivered as another spasm wracked through her.
“Not before I strap-on my big cock and fuck your slippery ass. And I still want you to fuck my ass while my big vibrator tickles us from inside my wet cunt.”
“God, you are so nasty. I love it,” I breathed in her ear.
She peeled down her soaked rubber panties and slipped out her butt plug. Jennifer sexily sauntered over to the closet and pulled out another pair of latex panties, sans dildo this time. She slipped it on and handed me the spray shine with a smile. Spraying it on, I smoothed my hands over the slick material and paid extra attention to Jennifer’s small, tight ass. She looked so wicked in her shiny black outfit.
We took a water break, our eyes still lingering over each others rubberized bodies. As we sipped our water to rehydrate from our overheated, sweaty session. We chatted about my work, and her work. She has a job in a woman’s only gym as a personal trainer. When I told her that I was a triathlete and she told me that she thought I was when she first saw me. “I have two women that I am endurance training right now,” she said, “and they have the same look in their eyes as you. Confident, focused and energetic.” I asked if she every combined this work with the other. “No way. Total conflict of interest. The only people who know that I do this are my clients, who I only see when they come to my apartment,” she replied. “I respect people’s confidentiality and expect them to respect mine.”
“That’s cool,” I agreed.
“Shall we get back to the fun? I think I have finally cooled down enough. What about you?”
“Yeah me too, and I think I have recovered from my last explosion.”
When we climbed back on the bed together, facing each other, our hands were in constant movement over each other. We caressed and teased each others nipples and shivered at the sensations. She reached for my latex cock and ball sheath and slid them back on my growing hardness. While caressing my encased cock and balls, one gloved hand reached under me to my pulsing ass and fingered my slippery anus. She easily slid two fingers inside me and groaned, “Nice and loose and slick. I think I need to fuck it now… with my big strap-on.” Crawling on the bed towards the side table she reached over me, her breasts brushing my face and I Iicked out at her protruding nipples. Jennifer halted in her reach, taking the moment to savour the caressing of her sensitive nipples as I massaged her engorged breasts in my hands.
She reached again and removed the small towel protecting the toys and pulled back the widest strap-on I have seen. It was a pink rippled soft shaft with a large head, three inches around at its widest and about eight inches long.
“Think you can take some of this? After that butt plug this should just slide right in.”
I gulped at the size of it, but whispered, “shove it in me slowly, gently… at first.”
“Can you help me get this harness on?” she said with lust in her eyes.
I helped fasten the harness while she adjusted the dildo in place.
“Fuck, I just love the feel of a big cock sticking out from me.” And it really did stick out from her small frame. “Do you want to suck it?” she teased.
“No thanks, I’m not into that. Just anal. Deep, stretching anal massaging my prostrate,” I replied hungrily.
“Ok hunny. Lay on your back with your legs up so you can see me driving it into you.” She positioned a large pillow under my ass and I adjusted myself onto it.
“This is my fantasy come true, watching your shiny latex hot body and gorgeous breasts while you fill my ass,” I whispered as we stared into each others eyes.
She positioned herself between my legs and with both hands guided the intruder to my pulsing sphincter. With the billiard ball sized head of the dildo against my stretching anus she started rotating her hips and forcing it into my wet hole. The stretching caused sweat to break out on my brow and I forced my breathing into a steady, muscle relaxing pattern. Slow and deep, just as in my triathlon training had taught me. Slowly the head slid into my ass past the first, then second anal ring.
“Good boy. Just keep using those relaxation techniques, it’s sliding into your ass now,” Jennifer exhaled. The next part of the dildo slimmed and my ass accepted it eagerly, until it hit my prostrate.
“It’s at my prostrate. God this is good… go slow now.” The curve in my prostrate slowly accommodated the intruder as Jennifer gently pushed her weight onto the dildo. The next large ripple in the strap-on hit my anal opening, causing my sphincter to protest. Slowly my anal rings stretched again and accepted it, as my prostrate already had.
“Oh fuck yeah! It’s filling me so good. Deeper,” I gasped.
“Oh Jack, I love fucking your hot ass. Only three more inches to go. One last ripple. I know you can take it now,” she breathlessly exclaimed. She lubed her hands and started massaging my now soft cock and full balls. Within seconds it was rock hard and standing at attention. The sensation through the latex made me forget about the dull pain in my ass as she slowly plunged the remaining three inches in my asshole. I barely even felt the last dildo ring stretch my opening.
Her eager hands picked up the pace on my hardness as I felt her pelvis grind against my anal opening.
“You took it. You took it all. How does it feel to have that entire dildo inside your greedy ass?”
“Oh fuck, Jennifer. It’s heaven. I’m filled so full. Fuck my ass now, please,” I begged.
“Here it comes baby. Take it for me, cum in my hands,” she replied lusciously.
Jennifer pulled back so my prostrate was still taking it, just three inches, and then plunged back in.
“Yeah!” I screamed, “Fuck me with your huge dildo. Fill my ass.”
She pulled back further this time, passed my prostrate, then put all of her ninety-seven pounds against me, opening me up again. My prostrate spasmed in delight and a wave of pleasure ripped through me.
“Oh my fucking God, yeah. Again. Fuck me hard now.”
She pummeled me mercilessly, slamming her hard dildo deep into my ass again and again, all the while forcefully massaging the cum from my inflamed balls.
“Ahhggghhhh, I’m cumming again,” I exclaimed.
“Cum for me Jack! Fill that latex! Cum in my hands!”
I nearly passed out as wave after wave of pleasure overcame me. It felt like my entire being passed through her hands.
“Ahhggghhhh, yes I’m cumming!” I grunted through clenched teeth, as my body convulsed in orgasm
“That’s it baby, give me all your cum… I can feel it shooting out your prick into me hands. Your pulsing cock feels so good.”
I screamed again as my load shot out of me, filling the latex sheath again and again.
Jennifer slowly slid the enormous dildo out of my ass, replacing my gaping hole with four fingers of her latex encased hand.
“I could almost fist your ass right now,” she said excitedly.
My cock still spasmed and my breathing slowed, but my mind reacted to what she just said, “That would be amazing! But not today. I just need my heart to stop trying to beat its way out my chest,” I gasped.
“I still want you to fill my ass while I fuck my vibrator,” she purred, “maybe another time, hey? After that orgasm I doubt you’ll be able to get it up again.”
“You’ve got that right. I’m spent. But I really do want to fulfill your fantasy too,” I said between breaths. “There definitely will be a next time, after I recover,” I laughed.
“You, my friend, are a first. I am willing to offer you a freebie to take me there next time.”
“Jack, we truly are two of a kind. And you really turn me on.”
“Jennifer, I’m honoured… I’m speechless. You are everything I’ve ever dreamed of.”
“Thanks Jack,” she replied honestly.
We cleaned up together, glancing at each other lovingly after our so intimate session. “Lovingly?” I questioned myself, “Well yeah – tenderly, caringly at least.”
She allowed me to shower and wash myself, while she finished cleaning the latex in the bathroom sink.
When she escorted me to the door she pulled me to her in a warm embrace, “call me soon, Jack. I’ll look forward to our next meeting.”
“Me too,” I said, as I returned her warm embrace.
To be continued. See “Jennifer two.”