The Toy Boy Call Boy Pt. 01

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Aunt Jane trains Jamie to become an escort for older women.
11.2k words
4.65
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Part 1 of the 2 part series

Updated 09/22/2022
Created 07/10/2010
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Chapter One

I guess that I was slow to get into sex. Growing up as a teenager in the naughties, one would expect that I would be fucking away like a rabbit from the age of around 14. But it was on the eve of my 18th birthday before I found a fellow student willing to let me have access to her body. As first times go, it was nothing to write home about and our relationship faded away shortly after. But at least I got that male virgin thing out of the way.

Then followed many months more without actually fucking. Oh sure, I enjoyed some touchy-feely with several girls, but I just seemed to go out with females who were not about to put out without some sort of commitment.

It's kind of weird, but my first really meaningful sexual encounter was with an older woman ... she was my mum's best friend. In our family, to my siblings and I, she was always called Aunt Jane as we were growing up. She wasn't really my aunt, not a blood relative, thank goodness. But when we were kids, Jane and my mum thought Aunt Jane was a good moniker for a gregarious woman who was even closer to us than any real aunt would have been.

Aunt Jane is my mum's age, now just past forty, and they had been best friends since high school. Whenever we had a family function, Aunt Jane was the first there and the last to leave. When my brothers and sisters and I were pre-teens, she would lead the party games, getting down on the floor on her hands and knees, even unconsciously flashing an inner thigh, a triangle of panties without concern.

I was 20 when I came home from college for the holiday season. Mum and dad had a dinner party this Saturday night. I wasn't part of their dinner and I had gone out with friends, but it was a dull night. The guys that I grew up with were just goofing around, doing stupid stuff, so I was back home by 10.30.

I dropped by the living room to acknowledge the 8 people there. I knew most of them, all friends of my parents. They had finished dinner and were just sitting around chatting. I didn't linger, just said "Hi all" and disappeared up to my room.

I scanned a few porno sites on my laptop, then stripped off and clambered into bed, electing to beat off my by now solid core of meat, so I could relax enough to sleep. Now I don't claim to have one of those super sized cocks, but I have to admit to it being a very solid 8 inches erect ... and thick too.

It took me most of my teenage years before I realised that not all guys had that much length stored in their pants. Only a few months ago, I had been making out with one young woman and she had exclaimed shock when she felt it hard within my trousers and insisted on taking it out to check its size first hand. She set out to convince me that what I had was a gift that I should be proud of. From then on, I found myself sneaking a peek at the other jocks in the showers after sports training or at the gym.

After doing some surreptitious research, I decided that this observant young woman was quite right. Not many of the other guys in the sports teams measured up to my cock. It gave me the confidence to strut around naked a lot and to chat up a lot more girls. My sex life began to look up.

So here I was, at home for the holidays, in bed at 11 on a Saturday night, one hand holding the sheet up while my other worked up some pace, stroking my hard-on toward some much needed hand relief. Now, you would think that any person other than my mum or dad, would knock before entering a 20-year-old boy's room. Well, not so my Aunt Jane.

She flung the door open in her customary cavalier style, bursting through it, "So my lovely Jamie, how are you? Is it good to be home?" She got all of that out in the time it took for her to make it from the door to the side of my bed, with the sound of the door slamming shut behind her becoming a punctuation mark for her words.

I, of course, abandoned my strokes immediately, my hands straightening down by my sides, the sheet floating down to cover my body. But that result was worse than being sprung wanking off, because the sheet cascaded down and tented very pointedly over my stiff and vertical erection, a wet stain immediately showing from the pre-cum on my cock tip.

It appeared that Aunt Jane was suddenly confused, unsure where to look. Her smiling face was taking in mine, but I could see her attention drawn to the wet-tipped totem pole that drew the sheet up around its prominence. "Oh dear, my timing's out, isn't it Jamie?"

I am sure I was red-faced, I know I felt hot and flushed, but that may have been due to how close I got to cumming, "Yeah Aunt Jane, you could say that. I wasn't expecting anyone to come."

"Other than you," she retaliated in her amusement, reaching out a hand and stroking it affectionately across my forehead, pushing back some strands of my hair, "I am so sorry, Jamie, I should have knocked. You're a big boy now and I should respect your privacy." Then, trying to lighten a tense situation, she added, "I just wanted to see my favourite boy, hear how he's doing at college. Are you studying hard, meeting lots of girls?"

I saw her eyes wander back along my sheet-covered body to stare once more at the shape of my hard-on, "Oh dear, I bet the girls at college really go for that." Then obviously realising what she had just said, she added, "Oh Jamie, pardon me, that's not a decent thing for your Aunt Jane to say. But it looks like you're a big boy now in more ways than one."

She giggled at her inappropriate double entendre. I didn't know what to do. There was no way that I could will it to go down in anything under 5 minutes, such was the effort that I had put in to raising it to its maximum length and girth. I considered rolling onto my side, but that seemed to be a stupid thing to do now that she had already noted its size.

To my shock, Aunt Jane reached a hand out and folded it around the sheet at the head of my cock, squeezing it firmly. "Oh my God, I'm your mother's best friend, I shouldn't be commenting about this, but you are very well endowed, Jamie."

"You're a woman, Aunt Jane ... tell me, is this a good thing? Do women like it to grow this big?" I don't know why I asked her that, other than my still naïve curiosity, since my experience with the opposite sex was still limited.

Her eyes seemed to widen and her hand wouldn't let go. She just stood there squeezing the head of my cock. "Oh yes, we certainly do." Her voice seemed to rise enthusiastically, "You are exceptionally big, Jamie, this would make a woman feel completely filled. That's a good thing, Jamie."

I wondered for how long she was going to hold it. Involuntarily, I thrust my hips upward, pushing it toward her within her grip. She emitted a strange sound, quite guttural, like a painful moan. "Would you ... oh dear ... Jamie, I know I shouldn't ask ... but would you ... would you mind if I had a look at it?"

Wow, I hadn't expected this. Was the situation getting out of hand? My Aunt Jane, whom I had known as a family friend, as my mum's best friend, since I was old enough to remember anything ... Aunt Jane was asking to see my erect cock.

"Err ... yeah, I guess so!" I told her, a slight tremble in my voice at the prospect of having this mature woman, that I had known all my life, stand there and examine the most intimate part of my body.

I felt the sheet tugging away from my naked chest, down over my belly and then the top hem of the sheet trailing over my cock-head and then exposing it, the solid core standing proudly upright ... long and thick. Aunt Jane threw the sheet away in her eagerness to see what had been exposed and it bunched over my shins and ankles.

"Beautiful, it is truly beautiful, a work of art. Jamie, you are truly blessed. That is big and thick, but the wonderful thing is that it's not disproportionately so." She tore her gaze away and looked in my eyes from where she stood beside the bed. "Do you get to use it much? Oh dear, listen to me, you don't have to answer that. I shouldn't ask, it's such a personal question. I'm sorry!"

"No, that's okay," I told her, "not a lot yet, but I'm hoping to. I only discovered a few months ago that I am bigger than the average guy."

"Oh, indeed you are, Jamie, indeed you are. I have seen one bigger ... in a strip club that your mum and I went to once, but it wasn't accessible to us. This is the first time I have ever been able to touch one so big."

Her hand reached out and touched the head again. But this time, it was skin on skin, her fingers fondling my hard knob, no longer obscured by the sheet. She would have seen my eyes close from the electric sensation of the way her fingers were arousing the sensitive underside of my cock, right below the head.

"Do you mind my doing this?" she politely asked.

"No!" I gasped, looking at her through slitted eyes. I saw her turn her head around to stare at the door. She must have been checking that it was closed. Then she let go of my cock-head and I was disappointed that the moment was over. But instead, she dropped her hands to her sides and each hand grasped clumps of the material of her dress and tugged up until almost all of her thighs had come into view. Just another inch and I figured I would see her panties at her crotch.

But while her hands climbed higher to her hips, the material caught on her wrists and the front of the dress hung down just far enough to keep her crotch covered. I was amazed, what was she doing? I saw her thumbs hook into the waistband of her panties and she hauled them down, her dress falling as her hands lowered, covering her pubes that would now be naked beneath.

I saw the panties fall, saw her step daintily out of them. She kicked off her shoes, then put one knee on the bed. I couldn't believe this was happening, my Aunt Jane had lust in her eyes. She crawled on her knees across to where I lay, lifted one knee over my prone body and shuffled up higher until I imagined that her pubis was hovering above my vertical hard-on.

Aunt Jane had let the dress fall down around my naked body, it totally obscured that intimate part of her that was about to come into contact with my body. I looked up into her eyes expectantly. "Oh God, please forgive me for what I am about to do," she pleaded, her eyes drifting toward the ceiling, apparently in prayer.

I felt her body, sizzling hot, some part of it touched my cock tip and it felt really good. She dropped a hand and it foraged in under her dress. I felt the palm of that hand wrap around my cock shaft and she began to guide my tip into the channel formed by her outer lips. To my surprise, there was already moisture. Was it mine - or hers - or from both?

I lay back and enjoyed her pushing my cock tip up and down between her swollen lips. Each time, she pushed it up to her emerging clitoris, I watched her face reflect the pleasure it gave her. Aunt Jane had not uttered another word after her brief prayer, seeking forgiveness, but now expressive moans were coming from her mouth, her slightly parted lips so appealing. I wished she would bend down and kiss me, not that my arousal needed any more help.

She might be enjoying manipulating my cock, but now my greatest fear was cumming before I even got inside her panting body. I tried to think of anything but what my body was feeling, trying to dismiss the arousal that was taking over my body as my pulsing cock twitched as it was dragged within her folds.

Thankfully, I at last felt her hand slotting my thick cock-head at her entrance. Then there was pressure from above, she was forcing her body downward upon me, making those intimate labia lips spread around my smooth knob. I felt the heat of her cunt as her downward pressure met my unwavering solid core, splitting her lips and my cock-head was swallowed up within the heat of her liquid passage. Was I in heaven? It sure felt like it.

The downward pressure eased once my whole cock-head was seated inside her hot body. I watched her face, saw the emotion, the passion, the lust, watched her body shifting around, adjusting to my size. Then when she thought she could cope, she was pushing down once more, swallowing up another inch or two of my shaft, the heat and velvet lining of her cunt walls burning my shaft.

This was unbelievable. Ten minutes ago, I was alone in my bed, beating my meat, striving for a feeble no-emotion, hand-made climax. Now my cock was slowly being enveloped within the heat of a desirable mature woman's body ... a woman that I had admired from a distance since I was an infant.

Inch by inch, her hot cunt took more and more of my cock shaft. The changing expressions on her face reflected how challenging she found my size at times. But at long last, Aunt Jane made that final push downward and I was fully seated within her clutching cunt.

What should I do now, my lack of experience showing? Should I take charge and roll her over onto her back and fuck her aggressively until we both cum? Regrettably, I thought, that is the stuff that dreams are made of. Aroused by the heat of her pulsing velvet cunt glove, I pondered how long I could hold off the inevitable. My balls were already tightening.

While I debated taking charge, the window of opportunity was closed as Aunt Jane began to slide her body up off my shaft until only the head remained enclosed, then surprisingly easily letting her body weight drive her cunt fully back over my erection. She picked up the pace quickly. I wondered if I should be thrusting upward to meet her down-strokes, but I knew that could lead to the premature finish I feared.

I contented myself with lying back and letting my teacher call the shots. She was getting into it now, forcing her body down and up on me with an ever-increasing pace. The sounds that she emitted promised that my early fears might be groundless. This was definitely a woman nearing an orgasmic peak.

"Cum with me, Jamie," she screamed aloud, causing me to nervously look at the door, checking to see that it was indeed closed. Her sounds and her grasping cunt were having the required effect on my own libido. I was getting close ... but she was getting closer. Her breathing was now in loud panting gasps, almost shrieks of carnal delight.

And then she came, powerfully, forcing her body down for one final complete swallow up of my throbbing cock. I felt her orgasm pulse around my shaft and I thrust upward within her, although knowing I could get no more of me inside her. But that final thrust pushed my own finish over the top and I blasted my hot cum deep inside her body.

It seemed surreal that my potent life-giving sperm was being injected with powerful thrusts into the warm body of my lovely Aunt Jane. She collapsed onto my body and I wrapped my arms around her back, holding her to me while she moaned and then sobbed. What could I say to her at this time? The woman was wracked with emotion, and I guessed she was wrestling with feelings of betrayal.

Her cunt gripped my hard cock like a vice as it milked every last drop of cum from me. Then we were still, her, still clothed, lying atop my naked body. Her sobbing eased and she lifted her tear-stained face to look into mine.

"That was beautiful, truly beautiful, but we both know I shouldn't have done that. I have crossed a line that should never have been crossed. I don't know how I can face your mother again. Every time I will look at her, I will be thinking of you and that gorgeous cock of yours pumping into me ... so hard and so vibrant. And then when I see you both in the same room, my God, I don't know how I will be able to do that."

"Don't beat yourself up, Aunt Jane, I have to take an equal share of the blame. I didn't push you away, did I?"

"Oh Jamie, are you kidding? You are 20 years old, with raging hormones. Can you imagine that you could actually push a woman of any age away when she had just disgracefully removed her panties and climbed onto your body. No, it's my fault."

A light knocking on the door abruptly interrupted our blame game. We both stiffened, our bodies still rapturously joined. Instinctively, I reached out for the bedside light switch and plunged the room into darkness, then rolled Aunt Jane over onto our sides. She was still facing me ... and the door, but my body was broad enough to obscure her from whoever might come in. So long as they didn't walk across to the side of the bed, then they would see her.

My back was to the door, but I turned my head and called out feebly, "Yes!"

It opened just a little and my father was standing there, framed in the doorway with the light of the hall behind him. "Sorry to disturb you, Jamie, I thought you were still up?" My cock twitched at that comment, conveying to Aunt Jane that I indeed was still up. She stifled a giggle. My father continued, "Have you seen Aunt Jane, we can't find her?"

"No ... no, I haven't dad," I lied, turning my head away from him and looking intently into the eyes of my new lover. She smiled back at me, amused by our deception.

We both held our collective breaths, fearing that if my dad stepped inside my room, he would see her and all hell would break loose. I heard, rather than saw, the door close because I still had my back to the door, my eyes staring intently into Aunt Jane's. At the sound of the door closing and with the disappearance of the shaft of light from the hall, the room was plunged into darkness and I celebrated our joint relief by thrusting what was left of my erection firmly back into her cunt.

"Unngghh!" she grunted at the re-slotting of my cock inside her, but she hugged my body to her and gave an infectious giggle that caused me to laugh with her. "I better go," she said, "I'll tell them I stepped outside the house for some fresh air." She planted a sweet kiss on my lips. It became passionate and I wished that we could stretch this intimate moment a bit longer.

The kiss broke and she forced herself off the end of me and slipped from the bed. She had got out of bed on the other side, so she came around looking for her panties. She must have felt my cum leaking from her as soon as she stood up because her need became more urgent. She slipped a hand up under her dress to attempt to hold in what gravity was releasing from her. I realised that she was getting away and I still hadn't seen the pussy that I had just been inside.

She bent down to scoop up her panties, "These were on the floor between the door and the bed, I wonder if your dad noticed them when he came to the door," she said.

She had to take her hand from her crotch to hold her panties open to step into them. I rolled closer and reached for her dress, holding it up, lifting it above her thighs. "What are you doing?" she asked as she placed one foot through one leg opening in her panties.

"You saw mine, I never saw yours," I told her, switching on the bedside light to see her bare pubis. She had a neatly trimmed line of pubic hair. Her outer lips were still swollen and open. I could see streaks of my cum around those lips and some on her upper thighs too.

"Not looking the best at the moment," she said as she lifted and placed her other leg through the pantie leg and sort of shimmied her body the way women do when they are pulling up their panties. "May I?" she asked and took the hem of the dress that I was holding, letting it fall back into place, trying to restore the demure Aunt Jane who had entered my room not twenty minutes ago. She blew me a kiss and was gone and I lay there, surveying my now flaccid, but still very wet cock, reflecting on all that had just happened.

I slept well, dreaming of Aunt Jane. I went down for breakfast late, fearful of what might be said, wondering if Aunt Jane had pulled off her re-entry to the dinner party without suspicion. Nothing was said, other than my mum's strange, "You got home early last night, darling." Dad and I ignored the comment. If he suspected anything, he wasn't saying.