Ch.17 Roleplay

“Heaven help me
I know just what I am
won’t you lend a hand
to this twisted little man?”

– Michael J Sheehey

Each time I thought about what I got up to in the lolly shop and the bus trip I got excited all over again. I was lying in bed on night, replayed that afternoon over in my head, thinking about how it made me feel. And being able to share the experience with Jeremy – and not feel guilty – started me thinking about how it could have been even better.

The one sensation I kept coming back to was the feeling of the breeze all over my body and the sense of vulnerability and freedom. I wanted to relive and increase that sensation without actually walking down the street nude. Though I admit that also began to imagine doing that.

Of course, the whole thought process got me incredible hot, so I stripped off and started to touch myself for another “Saturday night special”. Clearly I couldn’t walk to work naked but there was one way I could secretly be more naked all the time. As the pleasure began to build, I decided to immediately book an appointment at the beautician. Maybe just after I came.


Following Alison’s revelations, it was clear to me that she was ready to be a bit more adventurous and after five disappointing years in my previous relationship, so was I. Between visits we would call each other but it was difficult to have any fun when Alison’s only phone was in the middle of the flat and her flatmates were often home.

One night I was reading Alison’s latest letter that spoke of her need for me and how she was suffering heartache when I wasn’t there. I had a moment of inspiration, so I called up Alison and we spoke about the letter and how much we needed each other. I said that I had an idea about how to make our heartache work to our advantage. Alison was intrigued and asked me to elaborate. I told her that it would be a surprise but that she should think about how her body felt when I was there and when I wasn’t and that I would do the rest.


I spoke to Jeremy a few days before his next trip to Sydney and he told me to think about our heartache because he had an idea of how to make that work for our mutual benefit. He said that he would use that to surprise me – in a good way. I’d been to the beautician that day, so I had a surprise of my own for him.


I arrived in Sydney Friday night picking Alison up from work and taking her home. She had a mischievous grin on her face all the way there which I questioned her about, but she told me that I would have to wait and see. I asked her if she remembered the symptoms of her heartache and she said that she did. I said that that was good, but that she would have to wait until we got home for her surprise.


By Friday, I was so excited to see Jeremy that the last hour at work just flew by. Not only was he here again, but I couldn’t wait to see the look on his face when he saw the “new me”. I had forgotten that he promised me a surprise too so when it finally came it was beyond my wildest dreams.


When we finally got into Alison’s room and we were ready to go I told her that if she liked we would now play a little game. She agreed and I told her to just remember her heartache symptoms, as we’d discussed, and that I would do the rest. I said that I would step out the door and once she opened it that the game would begin.


I had made one more trip that week to buy something else for Jeremy. It cost me a full day’s wages but wanted to go the extra mile for him and it made me feel extra sexy. I told Jeremy to wait a minute before knocking.


I left the room waited a minute then knocked. Alison opened the door, curious as to what would happen next. She was wearing a sheer white nightie and the lamp light silhouetted her frame so that transparent material left nothing to my imagination. Momentarily thrown by her appearance, I spluttered that I was Doctor Holland and that I was responding to her emergency with a house call. She smiled as she began to catch on and let me into her room.

I said that I had been told that she had called my practice complaining of chest pains. She concurred, fully into the game now, and we went back and forth as I got her to list her symptoms and patient history. Sensing that she was ready for the next step I asked her if she was feeling any tenderness or swelling of her breasts.

Alison smiled and said, “Yes.”

Then I asked her if her nipples were sensitive, and her lips parted slightly.

“Oh yes.”

Finally I asked her if she was also feeling wet and tender between her legs.

Alison shuddered, “Oh god yes!”

Knowing that now it was time to proceed to the end game I said that I needed to examine her. At my word, she slipped her minuscule dress over her head and stood naked before me in the lamp light, shivering in anticipation. Her surprise for me was now there in all its smooth glory. Her fully waxed muff drew my eye and hardened my erection. Fit to burst, I pretended to disinterestedly, visually examine her, but I was actually soaking up every tiny detail of that spectacular specimen of bald, naked womanhood. Holy mother!

I reached out and gently cupped each of her breasts in turn with my fingertips, playing at feeling for swelling but pushing the game ever closer to its enviable climax.

“Does this ache?” I asked.

Alison sighed sharply at my touch as if her orgasm was a time bomb just about to go off. “Not painful, just sensitive and tender,” she replied.

I chanced a little more pressure, “And that, how does that feel?”

“It feels so fucking good!”

Withdrawing my hands, I asked her to turn around and lean forward. Alison closed her eyes and turned, reaching for the bedpost and bent over. She knew that she was now at her most vulnerable. She knew that her dripping, swollen pussy was inches from me. She was willing to play this game to its climax, so willing.


I stood before Jeremy, naked again but perhaps more vulnerable than I had ever been. I could guess his game’s conclusion but the path there was entirely in his hands. I knew I was safe with him, but it still felt dangerous to let another totally dominate me. He instructed me to turn around and bend over. I knew what he was doing, and I wanted him to do it. He could do anything to me, I wanted him to. I wanted this to be dangerous. I wanted this to be wrong.


Could I pull this off? It was now or never. I murmured some more doctor-like comments and then put my dirty little scheme completely on the line. Alison was definitely suffering from acute heartache, I announced, in fact quite the most severe case I had ever seen. Luckily for her though there were two things she could do to relieve the worst symptoms. The first were several exercises. I told her that in her current posture that she should use her free hand to gently massage her breasts, perhaps for a minute at a time each. I asked her to demonstrate for me and, smiling, she closed her eyes and grasped her right breast in her hand and began to stroke and squeeze it, sighing softly.


Bending before Jeremy, my legs apart, he instructed me to caress and squeeze my breasts. I willingly complied, as slowly as I dared, shaking inside at my willingness to degrade myself before him.


When Alison had massaged both her breasts, I told her that she should next take her master hand and slip it between her thighs and slowly stroke herself where she was feeling the most sensitive. She complied, touching herself expertly in a way I could never imitate. I was so hard now that I could barely keep my hands away from her as I watched in amazement at my good fortune to have met her.


Next, he made me reach between my legs and touch myself. The word ‘pussy’ had always seemed so odd to me before, but it now seemed so appropriate.

Jeremy was so bold to have pushed his game so far. Just a few months ago I would have slapped anyone who had even hinted at half the things we had already done. I used to think that I was not that kind of girl. “How had he done this to me?” I thought as I reached in between my legs. I used to be so nice. Everything was now on display for him, not just my body but also my most private of acts and more worryingly, the lengths that we both now knew that I would willingly go just to please him.


“There was one other solution,” I said, trying to maintain my air of calm. Alison stopped touching herself and began to turn around, but I told her not to stop. Realising the twist to my game she willingly slid her hand back and, after first making sure to make eye contact with me, slid a finger inside herself and began slide it in and out.

“The solution is a new product: JC26. It is a gel that could be taken orally, vaginally, or smothered on the skin. It is very rare, and I only have enough for one patient. Would you like to try?”

Alison slid her finger out slowly, stood up and turned around to face me, naked and smooth, just inches away and deliberately placed her moist finger in her mouth and, in a long-drawn-out motion, sucked it dry. She stalked over to the bed and lay down, and while caressing herself she spread her legs wide.

“Of course, Doctor,” she said with a sly grin and a beckoning finger, “fill me up.”

“I must warn you,” I said stripping and preparing to join her, “JC26 is highly addictive.”

“Ahhhh, dick me!”

I thrust into her deeply with a passion of the truly obsessed. Alison met each stroke with an equal one of her own. As we approached climax she breathlessly said, “Doctor, I have just one question.”

“Yes, what is it, Miss Benaud?” I grunted, almost done.

“Can the medicine also be taken anally?”

With that I was spent. Utterly stunned and turned on by what I had just heard, I finished in one heaving movement, Alison following me into release. I collapsed on top of her, neither of us speaking for an eternity.

“Never mind” she finally said, “maybe next time.”


Jeremy’s little game was so much fun. I wasn’t expecting to still be playing “Doctor” at 20 years of age and I couldn’t have imagined that it could be so X rated. I also had no idea that I would love it. I would like to pretend that I don’t know what possessed me to hint at bum sex, but in reality I did. My desire to push the envelope of what was considered acceptable must have been suppressed somewhere in the back of my mind, but all of a sudden it had suddenly been unleashed.

If I could but my finger on it – phrasing – I would have to say it was the moment Jeremy made me keep masturbating in front of him. That was such a turn on, to have someone witness my most private pleasures, which unlocked my hidden desire. Everything I had read about and secretly craved was now on. I was going to do it. I was going to do it all.


Alison loved my game and congratulated me on my imagination and prowess. I returned the compliment saying that her improvisation was testament to her own abilities and imagination. She was keen to know more about my sexual history saying that I’d already far exceeded all of her previous experiences. I put it down my ideas to reading my sisters’ Cosmo magazines when I was a teenager and getting ideas from there more than any actual hands-on experience. Alison told me that she had had only had basic intercourse before me so anything like blindfolds, role playing, and candles were entirely new experiences. She asked again if I’d thought more about threesomes. I told her what Sandy had said about setting the scene and she then became lost in thought while I used the silence to caress her and marvel at her beauty. We curled up naked again and gradually fell asleep.

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