Ch.24 Fumbling toward ecstasy

“All the fear has left me now
I’m not frightened anymore.”

– Sarah Mclachlan

In the morning I got up early, kissing Jeremy while baying him to stay in bed to sleep some more. I fixed our breakfast and carefully cleaned myself in preparation of the morning’s activities. I secretly hadn’t eaten in the last 24 hours so I was ravenous by then and eating breakfast now wouldn’t affect my plan. I was as ready as I could ever be, so I donned my apron and went back to rouse Jeremy for his morning treat.


The next morning Alison woke early. I stirred but she kissed me and told me to sleep in while she got breakfast ready. I cocked an eye so that I could watch her slide out of bed. I never got tired of looking at her astounding beauty especially when she was moving about in the nude. There is something about a naked woman’s natural movement that I found more erotic than someone trying to behave provocatively. Strippers and pornography were something that had always made my blood run cold but watching Alison walk across the room naked to get a glass of water, that was a spiritual experience.

As Alison padded toward the door, sans clothes, I felt myself going hard and as it had been almost three weeks without her, I considered having a quiet tamper in her absence. As if she could read my mind she stopped and looked at me over her shoulder.

“And no wanking,” she said with a cheeky grin, “you’ll spoil breakfast.” As she was about to step out the door she paused and said, “Unless I can watch…again,” and disappeared.

That cheeky admonishment of course got me even more excited, but also intrigued. It didn’t make any obvious sense, as wanking and eating breakfast were mutually exclusive, so something was definitely on the cards for that morning. I tried not to think about it and quickly fell back to sleep.

Some time while later I was woken by a kiss from Alison. In the gloom I could see that she was crouched beside me and seemed to be wearing a strange white dress.

“Breakfast is ready sweetie. Put your shorts on and come into the kitchen.” As my eyes gradually adjusted to the light, she began to stand, and it was only then that I realised that she was wearing a white apron. However, from the cut of the cloth, I could see her breasts peeking out from the side. She wasn’t wearing a top!

“Come in when you are ready,” she told me, her eyes indicting the bathroom. She stood and turned and walked towards the door. It was only then that I noticed that she wasn’t wearing any pants either. “I’ll be waiting.” And she wiggled out the door seductively. Touché provocation, touché.

I know a sign when I’m given one, so I jumped out of bed and gave myself a quick top and tail concentrating on my morning-breath. Something was about to go down and I wasn’t going to do anything to repel Alison if I could at all help it.

When I got to the kitchen, Alison was walking toward the table, in just her apron, with two plates full of breakfast goodies including bacon, eggs and toast. She indicated the seat that I should take and placed her plate down opposite me.

“Would you like coffee?” she offered.

“That’d be lovely,” I replied.

“Just one minute.” She smiled at me then spun around to again reveal her bum as she walked back to the kitchen bench. The coffee pot was in direct line from me, so I got an extended view of her sporty ass all the way there and as she slowly poured the coffee.
Alison turned around with the cup and instantly spotted me checking her out. She smiled and brought the cup back and placed it before me, leaning in so I could get a glimpse of her cleavage.

“Milk?” she asked playfully.

“Yes.” She turned and walked back to the fridge affording me another opportunity to ogle her behind from behind. She looked back at me again and returned with a small jug of milk. She leaned over and poured it into my cup.

“Say when…” When it was full, she sat down and then said, “Sugar?”

“Yes please.” She got up and again walked away from me. I’d forgotten all about my breakfast by that stage.

“One or two lumps?” Alison offered as she once again lent into me. I was about to reach out to touch her when she said, “A-a-ah! You’ll have to go and wash your hands if you do that!”

Alison sat down at ate slowly making obvious small talk to try to tease me as I wolfed down my food in vain attempt to get to her faster. When she was finally finished, she asked me if I had enjoyed my meal and then said that she would now have to do the washing up. If I hadn’t already picked up on Alison’s tone and intent, then her standing with her bum on full display over an empty sink for thirty seconds did the trick.

“Would you like a hand?” I asked, taking my cue and stepping up behind her.

“That might be nice, but I’d really prefer your dick.” Alison turned to face me. She put her hands around my neck and kissed me. I could feel the blood surging now that I was sure that it was finally game time. She let her hands slide down my sides and hooked her thumbs into my shorts then began to ease them down till they passed my quads and gravity took over. She moved down slowly with them, taking me in her mouth and sucking my whole length.

“Oh yes,” I said, expecting more attention from her expert lips.

“Don’t you want your treat first?” Alison said slyly.

“Isn’t this it?”

With that, Alison stood and reached for a bottle of olive oil that was close at hand from the cooking. She positioned it over my cock and let it drip out slowly, splattering me with the thick viscous substance. When I was covered, she placed the bottle down and began to slowly tug her hand back and forth along my length. From the base to the head and back down she worked the oil into me while my pleasure grew. Her hand dripped with oil which trickled down and onto the floor. For an insane moment all I thought about staining her mother’s wooden floorboards before the next wave of pleasure engulfed me and brought me back to reality.

Alison watched me with curious satisfaction, looking for clues that I was on my way. She didn’t have to wait long and by this point I didn’t care if she missed out on having any fun of her own. If this was her plan, then she must have known what she would do to me and how long I could last. I felt the moment approaching and by now she knew all of my cues too well. She let me go after sliding her hand up my length one last time and taking as much oil as she could onto her hand.

“Be gentle,” she whispered, “this is my first time.”

I was confused for a moment till Alison turned, bent over the sink and, reaching up from between her legs, slathered the oil onto her anus. My eyes must have grown the size of dinner plates. Then she rimmed herself with a fingertip and tentatively pushed her finger all the way in.


This was the last moment to pull out – so to speak. I had psyched myself up for this over several weeks and now was my last chance to draw back from the breach – so to speak. I could have easily redirected this energy and had Jeremy just take me from behind and he would have been none the wiser. From back there he would have still gotten a show and he could have imagined whatever he wanted. So, when I put my hand between my legs I had to do was give him the nod or guide him in as usual and it still would have been another perfect moment. But I was too worked up, I’d come so far in my journey, and I might never get the nerve to try this again. My decision was made when my finger touched my rim, all of my nerve endings on fire, and it felt so fucking good. I couldn’t unfeel that and from where Jeremy stood over me there was no chance of him unseeing it either.

With a little nervousness and a bit more pressure I found my hole and closed my eyes. The oil eased the way, but the sensation was akin to burning. I almost jumped forward, my left arm took my weight against the sink, but my boobs definitely jiggled. I worked my finger in and out for a moment and, the die cast, turned my head so I could look him the eye.

Trying to maintain my cool, I said, “Well, what are you waiting for?”


I untied Alison’s apron and let it fall way from her inclined body, her breasts now free of their feeble restraint. I paused to remember this moment and I slowly dragged my fingers, one hand at a time, from her neck to the small of her back, allowing each to settle on her hips. As I moved closer toward her, a visible shiver went up her spine.


Jeremy took my hips in his hands and positioned himself directly behind me. He inched closer until he was just millimetres away. I shivered, my body automatically defending itself against my will. As he made contact, I arched involuntarily, trying to curl away from him but his hands held me fast. My body would have normally craved him but now it was trying to recoil. How curious this situation. I could feel his slight pressure on me, just touching, almost reluctant. Ever the gentleman, he was only ever thinking of me first.

“It’s ok,” I heard myself say, “I want this.”

He paused a moment longer then began to ease himself in. I was on red alert, my body trying desperately to override my resolve. Even now I still could have called this off but a moment later it was too late, and he was in.

I had never felt anything like it, a sharp pain that was so specific and intense. The sensation was 10 times more concentrated than what my finger had just produced. A burning feeling coupled with a sense of tearing. I jumped and cried out but with the sink just inches away from my head I had nowhere to go. My body had one exit and that was to back away from the solid metal object and into the danger. I knew that I’d made a bad choice. But a moment later a sense of calmness overtook me. The pain didn’t get worse and quickly began to ebb away even though I was still visibly shaking and grunting when Jeremy began his gentle thrusts.

The initial shock now gave over to a feeling of mild pleasure. The pain was still there but it was bearable and was more akin to a slight sense of discomfort. It must have helped that Jeremy was being as slow and gentle as he could. I began to forget about initial shock and concentrate on the subtle pleasurable sensations that I could feel: the gentle rocking, the air on my body, my breasts swaying back and forth and the curious sensation of being full despite my day long fast.

In my position, I was able to hold myself up with just the one hand so that I could alternately squeeze my breasts and work my clitoris. Jeremy was taking longer than I expected and as my body was now used to him being in my bum I decided to try and get a little something for myself. My hand was still covered in the oil which made the feeling slippery and warm. I held my lips apart with my first and third fingers and began circling with my index, something that I’d been doing since I was 15 but had become more regular in the last two months. Despite, or more probably because of, all the amazing sex I’d been having since I’d met Jeremy, I constantly found myself feeling horny. I felt that I was in need of a release every day, and certainly at night if I had picked up and read one of his letters. In fact, anytime I thought about him at all I just needed to cum.

With this on my mind I kept working toward my own release and had almost forgotten about what was going on behind in my behind. It had now actually started to feel pretty good back there. Not the same as having his cock in my vagina but a brief intervention there by one of my fingers was a pleasantly stimulating shock that helped push me closer and closer to the edge.

We hadn’t been at it too long when I felt that Jeremy had started to quicken his stroke. He had excellent stamina, so he was more likely ending than tiring. I would have normally slowed him by altering my position or thrusts but as an experiment I was happy that this one had been a success. I had already thought about what would happen at the end and how best to avoid any potential mess on the floor. As Jeremy’s breathing began to shallow, I turned my head as far as I could and saw that he was ready.

“Cum in my bum,” I said.

A crooked half smile came across Jeremy’s face, and he began to thrust more forcefully. That hurt a little, but he still wasn’t really pounding it into me. I couldn’t complain, this is what had to happen if I wanted it to be over soon. A few more thrusts and his breathing stopped; his orgasm now inevitable. I slipped a second finger in as a reward for my sacrifice, working them both harder to squeeze a little more pleasure out of these final moments. Jeremy came soon after and collapsed over me onto the sink, his extra height allowing his arms reach forward and support his weight. I gave him a little while to recover before I told him to stay in me till he was soft. If anything, bad was to happen it probably would if he suddenly withdrew. We stayed like that for a few minutes until I felt it was safe and then we headed to the shower. 

For the remainder of that day, we lounged around the house, doing small chores but generally just relaxing and taking our time. There were lots of kisses and cuddles and even a little afternoon nap but nothing more. I was still feeling a little battered and bruised from the morning and Jeremy was sensitive enough not to ask for anything more that day. It was then that I found I had another reason to love him, his gentleness. We had been having reunion and farewell sex almost every week since early July. His passion for me was incredible and flattering but now that we had a little more time and I was in some discomfort – nothing bad, just still feeling it – I really appreciated his consideration and that I hadn’t had to ask him to back off. As I’ve said before, he must have worked out long ago that if he thought of himself last, he would eventually get his reward.

That night, I dropped Jeremy at the Battalion depot. I had the next two nights to myself to catch up on some study and relax in my childhood home. But after only a little while I began to miss him, in spite of his proximity which was now 100 times closer than usual. My thoughts then turned to what we hadn’t discussed on Friday night. My parents had been divorced since I was young, and I knew that mum had kept her ring for me to have one day. I went to her room and found the jewellery box. I took it out and put it on. It fit; I felt my heart skip a beat. It felt right. I was so happy I began to cry.

1 thought on “Ch.24 Fumbling toward ecstasy”

  1. […] She remembered that she had carefully planned out the whole event with military precision including the before, during and after. The only part she hadn’t been able to anticipate was the feeling of him being in her bum. It had hurt a little to begin with, she remembered, but after a little while the whole thing had been a fun experience. […]


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