Riders Wanted

Inside, Anne was sitting in a reception area watching TV. It appeared as if she had been waiting on us. She was an average looking woman, probably in her mid-to-late 30's. She had curly black hair, and averagely proportioned. She certainly didn't look the part of your typical lesbian. I noticed she was dressed in rather comfortable clothes, and didn't exude the medical type atmosphere I had expected.

As we walked inside, she quickly bounced to her feet to introduce herself.

"Nervous?" she asked Caitlin

All Caitlin could manage was an affirmative nod. But Anne's positive demeanor and understanding of the situation seemed to but her a bit more at easy.

"I bet you are, I know I was the first time," Anne responded. "But come on and follow me, and I'll show you back to the room..."

She led us down a small hallway. "This is my office," as she pointed it out, "and there are some of the consultation rooms... And here is what we call the 'activity room' and she opened up the door and allowed us inside...

*

... What we saw inside is what I would describe as a nice mix of functionality and warmth. There was plenty of wide open space on the mat covered floors, windows with the blinds pulled tightly shut, but also a few couches and lamps around the room. On one of the floor mats sat the Sybian, kind of awkward on the floor all by itself.

Anne locked the door shut behind her, and motioned for us to come sit next to her on one of the couches. When we did, Anne pulled out one of the attachments from a bag on the side of the couch and handed it to me. It was kind of firm, and not especially flesh feeling. It was about 4.5 inches in length. She instructed me over to a sink to wash it off, and then into an adjacent room for a condom and lubrication. It seemed very odd that someone was being so blatant and upfront with me about something I usually held so private, but hey, she was a sex therapist

As I walked across the room, the reason I was sent on my chores became quite obvious. As Anne scooted nearer to Caitlin on the couch, I was afraid she was going to make a pass at her. However, from the little dialogue I heard over the next few moments, I was put at ease.

Catching bits an pieces of the dialogue like "It's okay to be nervous, that's a completely natural feeling," and "I only do this because I know how the Sybian changed my life" I realized it was just Anne trying to put my fiancée at ease. "Wow," I thought "this woman really is a professional."

I kind of gave the girls their distance as they continued their conversation.

Then Anne spoke "Come on over Lance, Caitlin seems ready and *excited * to get started."

Anne pulled me over to the side of the machine and gave me a quick demonstration of how to control the Sybian; "This first knob controls the strength of the rotation" she pointed out, "and this second one the speed of the rotation." "Be careful," she cautioned "if you turn it up too high it can be painful, and remember TAKE YOUR TIME." I promised to do my best.

"Alright, go for it guys, have fun!" Anne said, "And if you need anything, I'll be right back here."

Caitlin's eyes shot at me with a look of death. I could read the words "she is going to watch?!?!" all across her face. But before she had the chance to speak, I put my hands behind her neck and pulled her towards me for a kiss.

Our kissing continued, but Caitlin still seemed a little uptight. As my tongue made my way into her mouth, I could feel the nervousness starting to give way to the passion. Caitlin freely admitted to me that kissing was one thing that excited her and I was determined to make her forget her frightfulness. I slowed things down, taking my time, slowly exploring her mouth. Occasionally I would suck or bite at her lip.

After about five minutes, I began to pick the pace back up. I knew I was in good shape when I thrust my tongue against hers and I could hear her give off the slightest moan and noticed her eyes tightly closed. Placing my hands beneath her butt, I slowly picked her up and sat her on my lap.

As we continue kissing, I allowed my hands to move across her. At first I rubbed at her neck and back as I way to relax her, but progressed to gently pulling her hair and grabbing at her tight butt.

From there I took a finger and gently lifted her neck, where I gently sucked and bit at it. I would just barely get the area moist, and then back off and gently blow on the area. As I continued I could feel my own excitement starting to build, and cautioned myself against going to fast. As a result, I moved back up to her mouth and resumed kissing her. In the meantime, my hands slowly undid the buttons on her blouse, and once undone, I pulled it off and tossed it aside.

Caitlin always wore padded bras, and always made fun of me as I tried to feel her up through them. "I can't feel a thing," she always joked with me. So in combination with my anxiousness, this logic led to me removing her bra shortly thereafter.

I took Caitlin and gently laid her against the ground where I could get at her more easily. Still kissing, I allowed my hands to cup underneath her breasts, and trace circles along their outlines. Meanwhile, I continued kissing down her neck, until my chin rested on her chest.

Stimulating her right breast with my hand, I moved my mouth towards her left nipple. Just when it looked as if I was about to take it in my mouth, I stopped and let my warm breath covered it. And so I continued my game for several minutes; licking and massaging every part of her boobs, but purposely avoiding her nipples.

As Caitlin's nipples began to become more and more erect, she took he hands and began to run them through my hair. After a few more minutes, the scalp message became more suggestive as she pulled downwards, begging me to give her nipples some attention.

After just a little teasing, I finally gave in. I twisted my tongue around her hard nipple, gently biting and sucking at it, with my hand, I roller her other hard nipple through my fingers. My actions were met with approval as she pushed my head harder into her chest, and she let out a few unconscious sounds of pleasure.

After a few moments, I switched sides of her body, allowing her other breast to be serviced by my tongue. In crossing her body, I took in the full beauty of her chest. Caitlin wore a 34B or 34C, depending on what part of the month you measured, her boobs were pear-shaped, and topped by short pink nipples. While average in size, her breasts were ripe, firm, and proportional to her body.

My repositioning allowed me to regain some coordination, and with my free right hand I began to trace my way past her belly button and against the waist band of her skirt. Almost immediately as I reached it, I felt Caitlin reach behind herself, undo the zipper, and pull the skirt away. Since she was showing no signs of hesitation, I decided to do the same.

Reaching inside her panties, I could feel her smooth pubic area. Caitlin always shaved her nether region, but I could tell she had just shaved that day by the lack of stubble. Continuing my way down, I could feel her lips. Tracing my way past them, I probed inside her folds for her wetness.

Finding her entrance, I gently teased around it. Feeling her moistness gather on my fingers, I made my way back up her lips, and applied some of her own juices around her clit. Just as she had taught me so many years ago, I placed my finger just to the side of her clitoris and began to make a slow and deliberate circular motion.

After just a few seconds, Caitlin stopped and said "C'mon, enough foreplay, let's get to the fun part already." I was in no position to complain.

As she peeled off her panties, she looked at me in all my clothes and gave a disapproving look. "Fair is fair," she said. So wasting no time, I stripped off my shirt and pants, and stood only in my black boxer briefs.

"Better?" she asked as she cupped my balls through the fabric. I gave an approving nod.

I applied more lube to the attachment as she began to straddle overtop it, and then spreading her lips, settled right atop the device. The attachment wasn't large at all, so I was confident she quickly acclimated to it.

"Everything alright in there?" I asked. She nodded in approval. I scooted over to the little control module, where I took each of the knobs and turned them between an eighth and a quarter of the way to full power, and then anxiously looked on.

Almost immediately I noticed her get this glazed over 'deer in the headlights' looked about her. I thought to myself "wow, these things must be amazing; we're getting one of these!" Then I realized she wasn't fixated on her pleasure, but had snapped back to the realization there was someone else in the room.

I quickly moved over to her, and sat to obstruct the view between Anne and herself. I resumed kissing and gently caressing her, as the machine quietly hummed beneath us. After about five minutes she had relaxed, closed her eyes, and was starting to get into the rhythm of the machine.

Moving back to the controls, I turned them up another eighth of a notch and began to intensely watch Caitlin and her reactions. She first leaned over and supported most of her weight on her hands placed on either side of the front of the machine. This effect was two-fold. Leaning over caused her clitoral region to come more into contact with the vibrating pad and with her weight supported she was able to gently thrust against the machine.

Secondly, her hips moved in a rhythm with the attachment moving inside her, her butt moving back and forth ever so slightly just over top the saddle of the device. It was quite an erotic side to see her not just sitting there, but interacting with the Sybian.

Then, her legs slowly began shaking as she let out a quite moan. This peaceful look came across her face and the trembling in her thighs subsided. Now Caitlin's legs shaking were almost always a sure sign she had an orgasm, but this one seemed so silent and tranquil. I didn't bother myself too much with the details, as I was confident of bigger things to come.

After what was about of minute of downtime, Caitlin was again closing her eyes and bucking against the machine. Sexily throwing her hair back, she looked me right in the eyes and moved her lips to the motions of the word "faster."

I was obedient and gave the rotation "g-spot" knob another quarter turn. This time, there was an almost immediate effect. She stopped her gyrating motion and sat firmly atop the machine, almost as if she was trying to force it to penetrate her deeper. Placing her hands at her hips, she felt her whole body up, stopping to give her tits a firm squeeze.

"Mmmm" she let out what sounded like her first intentional and clearly audible moan. "Oh fuck, Anne, this feels good."

To this point, I had been pretty oblivious as to that third person in the room. I was so intensely focused on Caitlin, I had almost forgotten about Anne. Shooting my glance towards the back of the room at her I found her with her skirt hiked up a bit and her panties visible.

"There you go, honey," she responded "just don't stop, come like a little freight train for me." I hardly noticed I had been sitting there rubbing my foreskin with the presence of someone else in the room.

As Caitlin appeared to be building towards another crescendo, she looked at me again and said "hold me." Pushing the controls aside I sat face to face with her and tried to maximize the body contact. I wrapped my arms around her waist and held onto her lovingly.

"NO! Hold me like this," she said as she reached around behind me took my hands into hers and placed them right overtop her breasts. "Just squeeze and pinch," she remarked, "none of that cute stuff."

And after that statement she appeared to drift off into another state of climatic bliss. Her body became tense and rigid; she thrust her self into my hands. Rather than just a light tremble, her legs began to spasm and she gripped onto the machine and then against my back.

Her speech was limited to a "ugh... yes... yes... YES YES YES", this time around as her orgasm seemed to last a lot longer as she slowly removed her nails from my back.

She again seemed to enter a bit of a refractory period again as she let out a deep breath and a smile. As the machine continued to work at the same pace, she used her finger to signal me to stand up in front of her. Once, I did I found my boxer-briefs at my knees and my penis in one hand, and my testicles in the other.

While normally deliberate and meticulous in her actions. She moved with an almost animalistic fury about her work. Using her left hands to alternatively cup my balls and rub up underneath of them, her other hand steadied the base of my penis as she brought her mouth over the head and shaft.

"Oh god, that's hot," I heard from the back of the room. Clearly it was Anne. Looking over my shoulder I could see her as she proudly had her fingers beneath her panties and was rapidly moving them back and forth.

"You can come closer and watch, if you want," my fiancée offered. This was something not even I expected. As Anna obliged and sat down just a few feet away, my mind began to drift off to fantasies of a threesome with Anna and Caitlin. I was quickly brought back to reality by the incredible things Caitlin was doing for me.

For about two minutes, I received the best blowjob I ever had in my life. That is, until the waves of pleasure started to possess Caitlin's body again. As her back arched, and what were once light moans turned to grunt's, her attention to me certainly faded.

Her breathing became quick and swallow, I was beginning to sense the wave of orgasms that was about to overtake her. She fumbled awkwardly with my dick in her hand. She had a start stop motion; almost as if she would pause to reflect in her own pleasure, forget about the task at hand and resume it, and then repeat the whole process just a second later.

Because of her earlier performance, I was already close to the edge when her difficulty began, pushing me to a point of frustration. At her pleasure built, she continued having more and more difficulties bringing me to the edge.

Eventually she just uttered "Cum on my tits, just do it yourself... I'm so close, cum on my tits." Somewhere in the back of my mind I interpreted this boldness as being a means to cover up her difficulties, and the fact she was so focused on her self. Meanwhile, the front of mind didn't care a bit. This was an opportunity I had never had, and to hear Caitlin talk like that sent tingles up my spine.

As she cupped her breasts I took my cock in my own hand. After no more than ten full strokes I could feel the familiar tightness build as I shot stream after stream of warm cum onto her chest. More importantly, as the final drops leaked from my dick, I sense that Caitlin was about to get off in an even bigger way.

Still basking in the warm afterglow of my own orgasm, I positioned myself behind Caitlin and took her breasts into my hand gently kneading and tugging at them, my hands massaging my still warm cum into her skin. I was able to reach over to the control module and shift both the knobs to about 3/4 strength, a considerable increase in the strength of the vibration.

Reaching across her smooth pubic area I felt for the top of her vagina, taking a lip on each of my fingers I spread her vagina as wide as my fingers would allow. This exposed her clit and wetness. Taking my free hand, I pushed her body forward, somewhere in-between her straddling the machine and a doggy style position. This had the effect of placing her clit directly on the vibrating pad.

Upon contact, she squealed and a shudder went through her body. With the slightest hip adjustment she seemed adjusted to the faster vibrations. With her bent over in such a vulnerable position, I could see her pink little ass. For a second, I considered stimulating it, but figured it wasn't worth the chance of ruining this situation.

Growing anxious, Caitlin started to become a little more agitated in her speech and actions.

"Oh shit, Oh shit.... mmmm..... God it's so good... "

During the lulls in Caitlin's vocal parade I could here the wet sounds of Anne going at herself. Glancing over I could see her neat pubic hair trimmed into a triangle with her panties pulled to the side and her clutching at her breasts through her top. Anne wasn't the focus of my attention, however...

Caitlin was pressing so firmly against the machine, driving the attachment deeper inside her, that the little rubber feet could be heard squeaking against the floor.

"Come on baby, I want you to cum hard for me," I encouraged her.

Then a look washed across her face that looked like a cross between an "O"-face and a laugh. I felt her back arch and become rigid. I playfully gave her ass a firm smack

"Fuuuckk... I am cummin - Ahhhhhhhhhh," she belted. And it wasn't your average scream she let out. She would have woken up the neighbors if there were any. It was a high-pitched shrill that told me she was enjoying herself and wasn't afraid to express it. Taking a breast in each hand, she squeezed and pinched as hard as she could and leaned over giving her clit the full vibration.

For what seemed like the next minute, I experienced the most erotic site of my entire life. Caitlin's eyes nearly bulged from their sockets as she tried to comprehend the feelings sweeping over. Her face was a flushed pale as her mouth shifted between a wide open face of pleasure and gritting her teeth as she pushed against the machine. Her hair was disheveled as it was tossed back and forth.

Her breasts and nipples were red from their stretching, as she tried to stimulate every last nerve end. The vinyl of the machine was covered in a combination of her sweat and wetness as she rode it into oblivion. From my vantage point I could see as her the lips of her vagina and pink ass clenched down as the throes of passion went through her. Her legs trembled as she held them tightly to the side of the Sybian, trying to anchor herself in place.

Meanwhile, she emitted noises that sounded like stuttering moans and little yelps as she lost control of her own buddy. Random cuss words and sexual innuendo flew from her mouth. And so for two minutes, wave after wave shook her body, each one seeming to hit harder and somewhere deeper within.

Then, almost as quick as the chain of events began, her body slowly began limp. The intense vibrations were too much for her overly sensitive clit and she quickly removed herself from the machine. Still almost too exhausted to move, she sat there and straddled behind the still moving attachment.

I came over and took her in my arms, picking her up and gently and laid her down on the mats beneath us. I gave her a kiss on the cheek. I laid beside as her chest heaved up and down in still heavy breathing. From the corner of my eye I could notice Anne adjusting her clothes back into place.

"So guys, same time next week?" she said with a chuckle.

Still exhausted on the floor, Caitlin nodded and her head and cracked a little smile. "Sounds good, she said, but I was thinking more like tomorrow."