Pretty Please


"I can, can't I." she said under her breath. She moved herself a little, seeming to change the position of me inside her. It must have been effective, because she started rocking herself, making little incoherent noises.

"It's for you love. Enjoy it."

"It's mine, Its's mine, Oh, shit, Oh God, Oh Fuck!"

I will not guarantee that these were the exact words she used, as her movements and obvious excitement was rapidly driving me to ejaculation. I tried to think of other things to prolong my performance, passive though it was. I tried to think of anything else. Anything. Think of food. Sausages and chips. No not sausages. Sponge pudding with custard pouring over it. No not pouring, gushing. It was too late. I had come. I tensed myself and pressed myself up against her, trying to maintain her pleasure as my penis started to go past its best.

"Have you come, my love. Thank god. Thank you" she squealed, and she went rigid upon me, just twitching slightly externally and less slightly inside.

She collapsed on me. Kissing, hugging, murmuring. Slowly she got her breath back. Then her hand snaked between us, and she carefully held the condom on my penis while she rolled off me.

"Oh, Bob, Bob, you can't know how special that was."

I think that I did, although I did not say so. Exhausted as I was, I realised that it would be best not to discuss sex with my ex. at that moment. There had been more enthusiasm in Sally's single act that in the total of my previous experience.

She removed the condom. Then bent down and gently kissed my penis, before one-handedly tying a knot in it (the condom, that is) and dropping it over the bedside.

More hugs, kisses, and sleep.

We awoke again to the sounds of traffic outside.

When we had both realised that the other was awake, we just hugged and kissed again.

"Any chance of some coffee?" she eventually asked.

Wearing dressing-gown and shirt again we were soon sipping.

We caught each other's eyes, and after a moment, we both just said "Thank you." with the result that we both giggled.

"But this is not getting my bottom buggered, is it?" she smirked.

"You still...? Are you sure...?"

She looked sadder now. "I must. I have to."

I looked into her eyes, asking for confirmation. She nodded.

I thought about it. So did she.

"The guide suggested we start with fingers or butt plugs, using some lubrication.".

"Damn. Did we get any lube? I don't think we did."

"You're right. Too much booze. Not enough thought."

"What time is it?"


"It'll be open again soon. If we can get a bus. Hurry up, get dressed."

This time we were lucky.

"Sally," I quietly asked as we snuggled on the back seat again. "I really don't want to hurt you again. Do you think, if we sort of shared it."

"What do you mean?"

"Well I'm not gay, or anything, but," and I moved in the seat at the memory of her touch on my anus, " I was thinking that if we sort of practiced on each other. I play with your bum. You play with mine. You know, we would have a better idea of what the other one is feeling."

"Darling man," she kissed the end of my nose.

I was glad that there was a different assistant in the shop. The guides had been insistent about not sharing toys, so we bought another set of plugs -- these were dark blue -- and the assistant helped us to a large bottle of the appropriate lubricant that was not going to rot the plugs we had chosen.

We were soon home again, lucky with the buses indeed, and were back in the bedroom with the various items out of their wrappers and lined up on the bed.

"Bob, before we start.?"

"Yes love, what?"

"Should we have some breakfast?" Was she delaying now?

We agreed. But we undressed and wore gown and shirt again. While she scrambled eggs and made toast and coffee, I allowed my hand to wander over her body, hindering her. She didn't complain, and seemed to encourage my hands to be more and more adventurous.

But we were hungry. We were not distracted too much. We ate and drank.

This, of course, started our digestive systems working, and as we took our second cups of coffee upstairs, I realised that I had to poo.

I had to wait, uncomfortably, because Sally got there first. Then we decided that having a shower might make proceedings a bit more, you know, hygienic.

This was just right. Naked and soapy in the shower we explored and gently poked. Her finger not only rubbed my anus, it slipped inside. I felt it pressing against a block. It was not unpleasant, just unusual. I felt and probed her and felt the tip of my finger similarly blocked. I gently moved my finger in small circles within her, and I felt the block relax slightly. Press, push, slide, circle. It happened so gradually. I could feel her finger just inside me, but she was so distracted by my finger in her that she had stopped moving it.

I stilled my finger, and hinted that she take her turn. She slowly penetrated me. It was weird but nice. Then I remembered a hint from the guide. I pressed down, as if I was trying to have a shit, and I felt myself relax, and her finger moved inward by a knuckle.

"Oh Bob?"

"Yes love. It feels good."

"You love. Try to shit?"

"What? I've just been." Then she remembered the guide as well. My finger tip could feel the unpuckering. The ring of muscle relaxed and I too felt myself inside her.

I pressed again, but she flinched.

"Not too fast. Let me get used to it. Your fingers are bigger that mine."

We stood there in the shower, water sluicing off us. We would each push slightly backwards as we felt we were ready. Gradually fingers delved deeper. Then we could go no further. We had been relying on the soap being slippery, and it had washed off.

"Shall we?"


We separated. We dried each other. We went through to the bedroom.

Sally broke the seal on the bottle of thick clear liquid, and squeezed a bit onto my finger. It felt cold and wet. Slippery but not oily. I sniffed it but smelt nothing.

Then she picked up the two smallest plugs. She held them behind her back and shuffled them.

"Which hand?"

I went to touch her right shoulder, but then changed my mind. I leaned over and kissed her right breast.

He right hand emerged showing the blue plug.

"You first then!"

"But I might have wanted the pink one." I protested playfully.

"No. Blue for boys. And from what I am looking at I would say that you were a boy."


"No, you first. Get comfy. How do you want to do it?"

I knelt on the bed, then leaned forwards to give her the best access.

The bottle made a sclurping noise, and I felt the wet coldness dribbling between my buttocks. In a moment her finger was there to halt its progress. I felt her smear it around. There was another sclurp, and I tensed expecting the coldness, but it didn't come.

"Ready love?"

Then I felt the coldness as the tip of the plug touched me. I think I tensed up.

"Relax again."

She held the tip there for quite a few seconds. She applied a bit of pressure. For a moment I resisted, but then I felt it slide inwards. Again I felt that pressure against the blockage, but now I knew what to do. I pushed, and it slid further in.

"Ooh you greedy man."

"How far has it gone?"

"A bit more than half. OK?"

"Yes, I think so. Try a bit more."

She pushed again.

"OK? Doesn't it hurt?"

"No. love. Not pain. Just sort of stretched. It's good though."

She pressed again, but that was wrong and I flinched. She pulled at it, and it slid put. She was saying "Sorry, sorry." but at the same time I was asking her to put it back. It slid back in until it felt as before.

"Go on, love, out and in again. Fuck me with it. Fuck me gently."

She pulled it out. I heard her put more lube on it, and it was back where I wanted it. She did it again. It felt the same, but I heard a gasp from Sally.

"It's nearly all in."

Out, in, out in, hold it, then a moments push and slight discomfort and I felt my bumhole contract around the stalk of the plug. I stretched my arm round to feel. The base of the plug was there between my cheeks. The hole felt full but not stretched, but there was a glorious full feeling inside.

I realised that I had been holding by breath, and was now panting. Sally thought that this might indicate distress, but no, I felt strangely great.

I tried to sit up, but felt the plug try to move. I put my hand to it and held the base in place. Then I straightened. The different angle moved the pressure within me. I squirmed my knees round until I was able to lie on my side and to carefully put my feet to the floor and stand. The sensations of changing pressures soon had me panting again, but the big silly grin on my face told Sally that all was well.

She came to hug me. I was still applying gentle pressure to the base to keep it in place, so her arms and mine crossed awkwardly.

"Let me."

One of her hands pressed on the plug. Both my arms, now free, embraced her. I hugged her. The movement shifted the plug, and it stretched its way out, and would have slid to the floor if Sally had not grasped its base.

I glanced at it. I could see it had brownish streaks on it. Sally saw them too.

"Come on." She took my hand and led me to the bathroom. "Get cleaned up, and its my turn."

I sat on the loo and wiped myself clean of lube and a bit of poo. Sally washed the plug in the basin. There was something really touching and special about seeing her do that. If she had not done it voluntarily then it would have been degrading. As it was, it was amazingly intimate.

I stepped into the shower to make sure I was properly clean. Sally dried the plug and took it back to the bedroom.

When I went back through it was to see her lying on her back on the bed. The pink plug was already half poking her. One hand was holding it. The other was gently rubbing her clitoris.

"Sorry Darling, my coffee was cold, and I couldn't think of anything else to do."

I sat on the bed beside her. I replaced her plug hand with mine.

"Is there enough lube?"

"Probably not."

I withdrew the plug and squeezed the bottle over it. I quickly smeared it all over, and then with my generously lubed hand started to rub round her bumhole.

Her free hand was now squeezing a nipple. I pressed a finger into her bum. I felt the blockage, the tight ring, then she took a deep breath in, and I felt the ring loosen. My slippery finger was right inside her.



I slowly withdrew my finger, then pressed it in again. I could see she liked it, so I did it again.

I withdrew, and pressed two fingers a little way into her.


I froze.

"A bit more."

I pressed. Both finger tips were almost through the ring.


She breathed in and out deeply a couple of times. I don't think I pressed any harder, the muscle just yielded and both fingers were there past the ring.

"More.. More. Give me the plug."

I withdrew. I could see that her anus was not closing tightly again. I pressed the pink tip against the shiny darker skin. Almost without resistance it entered, almost as if sucked in.

"Push. Push. Push."

I tried to keep time with her demands.

It was almost there. Another half inch to go. She was panting now.

She was so much smaller than me. The plug was the same size. I was worried about doing real damage to her.

"Are you all right? Does it hurt? What do you want?"

"Yes. Yes. I mean no. Just push it you bastard. Don't fuck about with it"

However I decided that that is exactly what I would do. I pulled it out a bit, she swore at me again. I pushed. She told me to do it again. I did. And again.

"Oh thank you, thank you, thank you." she panted each time I pushed.

A quarter of an inch.


"Thank you you glorious bastard." It was there, in place.

She lifted her head. Her eyes were wide open. She had a look of amazement on her face.

"Sally, tell me if I don't do this right"

I leaned over and moved her hand away from her clitoris, and gently replaced it with my lips. I kissed the little bud, and then gently licked it. Sally's back arched. She writhed. She squealed. For my first ever attempt at oral sex the results were gratifying, to both of us. I think I must have done it right.

"Do you want me to take your plug out now?" I asked.

"Don't you fucking dare..." changed into "Not yet love, I'm still coming." while being punctuated by grunts and twitches. However, about two minutes later she waddled desperately off to the loo, one hand holding the plug in place. She felt that if it came out she was in danger of dramatically following through, but it had just been her body's reaction to the fullness. In the bathroom she was surprised to see the pink intruder emerge almost spotless. I took it from her and washed it, while she wiped herself and showered. Then we went back to bed.

You know the script by now. Kiss kiss, hug hug, sleep, sleep.


"Yes Bob?"

"How do you feel?"



"No. You?"


"But not again just yet."


We both went quiet.

"But I'm hungry."

"So am I."

The pub near bus stop did some food. The sort that you knew came from factory to freezer to plate, with chips on the side, but we enjoyed steak pies and pints.

As we left there was the unspoken question of if she was coming back to my house. I put my arm round her and led her there. I found a half empty bottle of scotch, and we chatted as it disappeared.

We chatted, went to bed, and chatted more. The alarm woke us. We were in each other's arms, and I realised that my arm had gone dead. I flexed my fingers, and awkwardly withdraw my arm and rolled out of bed.

"I have to go to work. Do you want to stay here? Do you want me to bring you tea? Coffee?"

"No love. I am working this afternoon, and have to do the washing before then."


"Yes, towels and sheets. Clean ones for each punter."

I could not remember seeing a washing machine in her kitchen.

"How do you... Have you a machine?"

"No, a laundrette."

"It must cost you a fortune. Use my machine, downstairs."

"Can I. But I need a dryer."

"There is one. I don't use it much, but I think it still works."

I left her. I gave her a spare key and left for work.

I got home at about sixish. My kitchen was tidier than it had been for years. It had that warm moist clean laundry smell. On my table was a note.

Dear Bob,

Thank you for a lovely sexy caring weekend.

Being here, on my own, I have been thinking that what I did was wrong, and that you might now be having second thoughts. I will understand if you do not want to see me again. Do not worry. I will be discrete.

I will ring you tonight when I finish work and will accept whatever you tell me.

I hope you do not mind. I know that you paid for them. I have taken the pink toys with me. I will pay you what I owe you when I can.

Lots of love and thanks


p.s. I have been playing again this morning and managed the middle toy. X X X

What was she telling me? Was she being straight with me? Had she just been using me? Had I been stupid. But on the face of it the letter meant just the opposite. Was she making an excuse for herself, or was she really showing me huge respect. I was confused.

I wanted a drink. I had my hand on the door-handle to go to the pub, but I realised that I did not want to risk missing her phone call.

I opened a tin of soup and ate it without really tasting it. I went upstairs to the loo. My bedroom door was closed. I never bothered closing it normally, so it looked odd. I opened it and went in.

The room was neat and tidy. The duvet had a clean cover on. The sheet under the clean pillows was fresh. On the bedside table, next to the telephone were the three blue plugs and the lube bottle. From somewhere she had found a scrap of ribbon which she had used to wrap the middle sized plug with another sheet of paper. I pulled the ribbon and paper off, and read another note.

If you do play with this. Think of me. Enjoy.

I sat on the bed. I unlaced my work-boots and took them off.. I dragged off my socks and threw them towards the laundry basket. When I saw them untidily there on the floor I stood up, picked them up, and put them in it the basket. I felt dirty in my work clothes. I stripped and went through to have a shower.

I picked my dressing gown off its hook. Underneath was the shirt she had worn. I wasn't sure if it was a whiff of her natural smell that came off it, or if it was just the way that my gown had been surrounding, almost protecting it, but I felt somehow very close to her. I found myself back, sitting on my bed, and I was caressing the plug that had been unwrapped. It was dry, and felt not quite right. It should be nice and slippery. I squeezed some of the lube onto its tip, and watched it dribble along its length. I rotated it to keep it flowing. Then I rubbed it with a finger to spread it evenly. Now it felt better.

I closed my eyes while rubbing the plug. I imagined Sally, lying on this same bed with the tip of the pink plug just entering her. What position had she used? Would she have been on her back or front? Kneeling? I knelt on the bed to find which was best. At I pressed the blue plug to my arse I felt a warm glow grow within me.

"Oh Sally, that's good."

I pressed it in quite hard. Too hard. It hurt me. This is what it must have been like for her in the shower. I felt guilty again for having caused her pain.

I pressed it in again, but more gently.

"That's better Sally. Slowly now."

I was imagining her hand on the plug, not mine.

"Push Sally. Push."

"Wait, wait, wait, hold it there."

"I love you Sally."

"Fuck me with it."

"In... Again... Push push push PUSH. STOP."

"Oh Sally, I feel so full. Is it nearly in? Fuck it a bit."

I fucked myself with the plug, but it was not sliding easily. I needed more lube. I withdrew the plug and grabbed the bottle and squeezed. I missed, the glob landed on my buttock. With my finger I sort of squeegeed the liquid towards my entrance. I felt it dribbling into me. I pushed my finger into it, again and again. I was so open. Inside it was so warm and soft, and now slippery.

"Now Sally. Try again."

I pushed it inwards. I fucked myself with it. Now it slid easily.

"Push. Push. Hold it."

I took a couple of deep breaths. I readied myself for the big push. I felt as if I was pushing out a huge great turd. I pushed. I felt myself giving way. With my hand I gently increased the pressure.

"Now Sally, Now."

It was in me. My ring of muscle had passed the widest part of the plug, and was now relaxed around its stem. It had felt almost too much, but only almost.

"Sally. Sally. I love you Sally."

I rolled onto my side, and straightened my legs. This made my buttocks press against the plug's base, changing the feelings.

I rolled onto my back.

"Oh, Sally, that's so nice."

I imagined that the hand caressing my penis was hers.

What time would she ring? Could I wait with it inside me until she did? I could talk to her and tell her I love her.

I was a little out of breath. I forced myself to relax. I found that my anus gave involuntarry twitches, and that when this happened I got a twinge of pleasure deep within my groin. I tried to encourage and emulate the twitch. I had been sweating, now I felt a little chilled. I slid under the duvet.

The telephone woke me. I tried to sit up quickly, but the plug made it presence felt a bit uncomfortably. I should not have fallen asleep with it in place. My bum was telling me that it wanted it out, as soon as possible. I carefully manoeuvred myself so that I was sitting on the edge of the bed, and picked the phone up.


"Oh thank you, Bob. I thought that you had decided not to answer it."

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