The Toy Boy Call Boy Pt. 01

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"Are you talking about my flabby 40-year-old arse?"

"It's not flabby, I told you, it's a great arse."

She peeled back the bedclothes and sort of slid in under, seeking the sanctuary of their concealment. "I tried to imagine how this moment would be, whether it would be awkward."

"Was it like this in your imagination?"

"No, I didn't expect to be so shy about my body. It's just that when I saw your tight hard youthful body, I suddenly felt embarrassed at mine that has seen better days."

"Don't put yourself down, it looked pretty good from behind ... trim and terrific."

"You're too kind, Jamie. So do I get to see the rest of you? Are you going to take those off?"

I placed my fingers into the waistband of my boxers. She would by now be able to see that the material was well tented out in front. "I don't know if I should, I still haven't seen all of you. I might just climb in there with you without revealing."

"Don't you dare, Jamie. If you are intending to put that inside me..." she nodded at my bulge, "I want to know what it looks like."

My fingers pushed my boxers down, easing them out and over my three-quarter extended erection, exposing my large cock to her gaze for the first time.

"Oh my God!" she exclaimed, "it's enormous."

Worried that I might put her off so close to our anticipated coupling, I defended my size, "No it's not, it's only a bit bigger than average."

"I never thought about size, never expected you to be so much bigger than my husband. Oh shit, what do I do now? I don't think I can do this ... I can't afford to have you stretch my insides."

"That won't happen," I attempted to reassure her, "when I realised that I was a bit different, I checked. A woman's body is so flexible, your passage will just go back to the way it was when I pull out."

"Oh dear, are you sure? My husband will wonder what has happened if you stretch me permanently."

I pulled the sheet back from her body, revealing her breasts, they looked good. This time, she didn't try to hide them. I slid into the bed alongside her, the length of my body matched to hers, I on my side, she on her back. I leaned forward and kissed her. She accepted the kiss and my tongue eagerly, perhaps seeking the intimacy to overrule the hesitancy that my size had brought to the moment.

The kiss became more passionate and my hand roamed across her breasts, teasing her nipples to hardness, then a feather-light touch across her bare belly and down to the junction of her thighs. She whimpered when my fingers traced the line of her outer lips and I felt her hand reach out to me and touch my hard-on.

My mouth vacated her lips and moved to cover her breasts, first one, then the other while my fingers continued to trace the outer lips of her pubis that were opening up to my touch, the moisture emerging. She whimpered more as my lips devoured her nipples and my fingers explored from her budding clitoris to her opening cunt.

As I lifted my body up and straddled hers, pushing my legs between her thighs, she implored me, "Please don't hurt me with this," and her hand fondled it, leading it to her entrance in spite of her fears about size. I slid it once, twice, up along the parted lips of her labia and she moaned enthusiastically. Then I pushed forward and she uttered a loud, "Ungghhh!"

I lifted my head to look down into her eyes, "Are you okay?"

"Yes ... yes, it was just the surprise of it ... you feel different from my husband. Don't let me put you off..." She raised her legs and wrapped them over mine, her heels on the backs of my calves. "Go on, do it again, I'm ready."

I pushed as she requested and the wet velvet lining of her liquid cunt swallowed up my cock-head. "Oh yes!" she breathed huskily.

I dipped my head and my lips claimed hers again. Our tongues clashed and writhed together and her hands dragged across my back, urging me into her. I pushed forward once more and more of my hard cock plunged into her.

All through this evening, sitting alongside her at the table at the Conference Banquet, I had studied her. She was the consummate banking executive, so confident and self-assured. Over the hours downstairs, I had pondered what she would be like in bed. She appeared so demure and conservative. All along, my expectation was that I might have to work hard to give this woman what she wants.

But now, with my cock sliding deeper and deeper inside her tight passage, I was seeing a different side to this woman. She had enfolded her legs around mine like a hot sexual being, eager to be taken. With one final lunge, I drove my whole length into her and she seemed to soak it up, her fingers now clawing my back.

"Oh my God, that's big!"

"Are you okay with it?" I checked.

"Are you kidding me?" and her heels dug into my calves like a jockey urging a racehorse to the winning post. "I love this," she enthused.

We were off and racing as I kicked into gear, driving my piston-like strokes in, slowly at first while we set up a rhythm, then gradually building up some pace. On the advice of Aunt Jane, I listened to Kay's breathing, checking for telltale signs that I was hitting the right notes on her keyboard.

I began my own mind games, attempting to seal off the arousal that this hot mature woman's body was igniting, firing up my juices, tightening my balls. I heard her body responding to me, she was quite a surprise packet. Don't judge a book by its cover, they say. They're right ... Kay loved every minute, her body absorbed my size without complaint ... well, after she had adjusted to its girth.

I was happily relieved when her breathing signalled that this was a woman in heat, a woman on the verge of completion. She was trying to push the pace, so I responded, giving her exactly what she wanted, thrusting my cock hard and firmly into her yielding cunt. Then her gasps, her moans, her shrieks of fulfilment as her body crashed over the top. I was still trying to hang on, but I doubted that I could stall long enough for me to get her to cum again. So I gave it four or five more hard driving thrusts and my cum burst from my tip embedded so far up inside her body. She would have felt every spurt of my life-giving juices.

My last recollection was of gazing down on a most contented woman, whose smiling face reflected the pleasure she felt while her tight cunt continued to pulse around the last of my spasms.

Somewhere in the pre dawn, I awoke to the wonderful sensations of a feminine hand stroking my cock back into strength. The room was in darkness, with just a thin strand of light from outside coming through a gap in the curtains. "Umm!" I murmured happily, reaching out a hand to lightly touch her hair, her face and then her breasts. "How long have you been awake?" I asked.

"Oh, I don't know, it could be half-an-hour."

"And how long have you been touching me like this?"

"From the moment I woke," she replied and I laughed. "Can you do it again to me?" she asked.

"Of course," I told her with my cock now hard and ready once more. "How would you like to do it this time?"

"Oh, I don't care, so as long as you can make me feel as good again."

"That's a big ask, I'll try."

She seemed like she was lifting her body up to perhaps sit on me. It was difficult to know in the dark, but then suddenly she was gone from the bed, "What happened, where are you?"

"I'm sorry," I heard her call from across the room, "but nature calls. Keep that erection for me."

I saw a bright shaft of light enter the bedroom as she disappeared into the bathroom. The light stayed, she had left the door ajar. I lay there in bed, contemplating how I might take her this time. Inspired by an idea, I too got out of bed and moved across the room to the open doorway of the bathroom. Kay had risen from the toilet seat and she looked up when she sensed my presence.

"I am coming back," she said.

"I thought of doing it in here."

"In here?" she queried, looking around her, "there's nothing comfortable to do it on in here."

I stepped into the small bathroom and bridged the gap between us. I took hold of her naked body, her embarrassment gone, and spun her around so that she stood facing the large mirror above the vanity. I placed both her hands on the vanity, and brought her lower body back so that she was bent forward from the waist, facing the mirror, her legs wide apart.

I stepped in behind her, wrapping the front of my body against her back, my belly against her naked arse. My hard cock slipped into the wet channel of her spread lower lips. Her head was down and she must have seen the smooth knob of my cock appear from between her legs. I know she felt it because she moaned audibly.

"Watch us in the mirror," I instructed as my hands folded around her B cup breasts, massaging and manipulating them into keen arousal. She looked up and would have seen my face alongside hers, my head behind one shoulder. I pushed my hard cock along her wet slit, the knob each time reaching to stroke her clit, each slide drawing an expressive sigh from her.

"I've never done anything like this before," she admitted.

"Neither have I, it just came to me in an inspired moment."

Her breathing was quickening already and I wasn't even inside her yet. "How does it end?" she managed to say, obviously overcome with the passion of feeling my hard-on at her most sensual spot while also being able to watch the intense feelings being done to her. "God, this is so erotic."

"Do you feel like a voyeur, watching your own seduction?"

"Yes, yes I do ... oh, can you put it in me now?"

"Does that mean you're ready?" I checked.

"God yes, don't talk, just do it," she implored, her face reflecting her intense need.

I used my hands on her breasts to hold her body steady while I adjusted my pelvis, feeling my rampant cock-head slot into her juicy opening. I stared into the mirror one more time under the harsh light, studying this mature woman's body. It was quite good for early forties. She looked up and saw me studying her, "Please," she begged, "just do it ... now!"

I shoved forward with my pelvis, seating my thick cock-head inside her cunt from this awkward angle. She would have felt it splitting her, engulfing her tight cunt and her face reflected all of that. Her hand shot down between her spread legs and she seemed to adjust my angle of entry inside her, complicitly helping me to take her once again.

"Ungghh!" she grunted each time I slotted more inches inside of her needy body.

This fuck became the most exciting and inspired in my oh so brief sexual life. Kay had obviously never experienced a man this way before either. Was it coming into her doggie style that did it ... or us being able to watch the passion and emotions on each other's faces as I plunged hard and deep into her willing body. It was probably both as I delivered our bodies to another pulsing, satisfying finish, filling her once more with my hot cum.

We were left just hanging there in front of the mirror, sweat plastering our hair across our foreheads, tottering on shaky legs until we could no longer hold our bodies up. We somehow managed to get back to the bed and crashed, destined to sleep once more and beyond dawn.

I woke with a start to the sound of someone at our door and I felt the top sheet thrown over my head. Kay was saying, "Stay there, don't move." I tensed, unaware of what was going on. Then I heard her speaking to someone at the door, heard the clink of silverware as a tray was put down somewhere in the room. I guessed it was breakfast and she was careful not to have me seen in her room.

After the room door had closed, I felt the sheet pulled back and I opened my eyes. My client, Kay looked sexy in just her bra and panties, she looked like she may have showered already. "Wake up sleepy head," she said, "I've ordered breakfast for us."

"Wow, that's great. I am hungry."

"I expected you would be after the energy you burned up in my body last night." She stood alongside the bed, her eyes dreamy, one hand reaching down to stroke along my naked body. "Jamie, you exceeded my expectations, thank you."

"That's good, you were a hot woman last night," I complimented her.

"And I'm not now," she said with a disappointed look, doing a little pirouette, clad only in her bra and panties. For a woman twice my age, I had to admit she did look hot. Not like a playmate or a each babe, but a slender mature woman without too much cellulite.

"No, you still look good," I reassured her and she reached out and pinched my cock that was flopped flaccid across one upper thigh.

Kay became serious, "I just want to tell you that you were good for me last night. You made me feel the way I wanted to feel ... the way I had hoped I would, but was unsure if this tired old body could light up like that. But it did, because of you." Her gaze switched between my face and my dormant cock, "I had never thought about size, that you might be different, bigger. That never occurred to me, how naïve am I?"

"I am still getting used to that myself, that girls..." I checked myself, "...that women would find me different from other guys."

"Maybe you should advertise that fact on your website. There could be some women who might be put off by that. I have to say that I had a hesitation when I first saw it. But I was so hot for it, so determined to have you ... and yes, just a bit tipsy ... that I put any fear of being hurt out of my mind."

"I am glad that I could deliver for you," I said, "now let's eat."

We sat at the table and enjoyed our breakfast. We talked a lot about sex, and a few other things too. She was stunned when I took a chance and admitted that she was my first client. "You were right not to tell me that," she confessed, "there is no way that you would have got the job if I knew you had never done this for a woman before."

"It's not like I was a virgin," I defended.

"No, but it was a big chance to promote yourself as a young man able to deliver on the desires of an older woman without ever having had one before."

"I do have a mentor, my Aunt Jane."

"What? Are you having sex with a relative? Well, that's just great!"

"No," I laughed, "she's not really my aunt. She's a friend of my mum's who has known me all my life and she is guiding me in this new venture. She had my webpage designed and has made some calls, looking for clients for me. Maybe that's how you found me."

"I don't know your Aunt Jane, I think my PA found you through contacts at our advertising agency."

"There you go, my Aunt Jane words in an ad agency."

We finished breakfast and I went to take my first pee of the day. With needing to pee and the usual phenomenon for males of morning wood, Kay must have noticed my half arousal as I walked off to the bathroom. When I reappeared, she was back standing beside the bed, her panties were on the floor beside her, but she still wore her bra.

"Can you come over here, Jamie? I thought we were done, I've even had a shower, and I do have to get to the office. But seeing your penis again makes me think that just maybe we have some unfinished business. Can you get on the bed please?"

I wasn't sure how I would go for a third time, but being a young healthy man, I was willing to give it a go. I stepped around her and lay on my back on the bed. She followed me onto the bed and kneeled her way across to me, lifting one leg to straddle my body. She quickly edged upward until her pubis was hovering above my erection that was stiffening quickly in response to the thought of one more go with the lady banker.

She was wet when the outer folds of her labia captured my cock tip within them ... too wet to be natural, surely. "I thought I might need a little help for a quickie," she said, discarding a tube of KY to one side. "Ooh!" she exclaimed and her face screwed up as she winced with pain. "This might be harder than I thought. My God, I'm sore down there, must be the size of you."

"Might be the fact that I'll bet you haven't done three times in a night before."

She laughed, "You're so right, this is so not me."

I felt her hands on my cock, adjusting my angle, testing my rigidity. Then with a "Oh God, here goes," and an exclamation of pain, she shoved down hard over my cock, presumably scraping her tender grazed insides around my erection.

Kay tried to slide up and down on my pole, but I could see the difficulty she was having. She seemed determined to have me one more time, but the excesses of last night made constant friction difficult for her. I solved her problem by bringing my thumb to her clitoris that was soaked in the KY she had spread around. While she held steady sitting on my hard-on, I thumbed her clit to one final pounding finish for her and she collapsed upon my body.

As soon as the pulsing diminished, she lifted herself up off me and got off the bed. She bent over to pick up her panties, her back folding forward, her arse spreading, the eye pointing back at me from just a metre away. Was that intentional, did she realise what that does to most guys? In that splendid quick moment, I could see it all laid out before me. There was redness all around her cunt opening, obviously from the over-use she had already acknowledged. But as her arse cheeks spread, that tiny winking anus was as unblemished and pure as it could be on a just showered woman.

Then the moment was gone and she turned to face me, hauling up her panties. "What?" she said when she saw the look on my face, "What's wrong?"

"Nothing, there's nothing wrong. I told you last night that you had a great arse. I was just admiring it again."

"Oh dear, did I...?" She looked genuinely embarrassed at having exposed herself in this way and I began to wonder if it was accidental. Whatever, I had enjoyed the moment. "I will never understand what men see in looking at a woman's arse," she continued.

Kay hurried away to find a day dress to wear from the closet, then I lay back and watched her pack her things. "I have to go," she at last said, "I was due for a meeting at the office 15 minutes ago. I should never have attempted that final try, but thanks anyway, I feel good now. Listen, stay here in the room until the 10am limit. Most of the bankers should have checked out by then."

She leaned over to kiss me, again quite passionately. "Thank you Jamie, you were wonderful. This was only intended to be an adventurous one time only. But if I ever feel tempted again, you will be the first one I will call. I wish that I could help you by recommending you to others, but you must realise that in the circles I mix in, I would be reluctant to admit that I had done this."

She turned and wheeled her suitcase to the door, "Oh Jamie, I left a little something extra for you. Thanks!" Then she was gone. I was curious, I got out of bed and walked across to the table where we had had breakfast. There was $250 in cash, she had left me a tip ... my first client and my first tip.

To be continued...

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  • COMMENTS
11 Comments
amoroneamoroneover 1 year ago

I also enjoyed this story. Very well written with pace and eloquence.

CroonyCroonyover 2 years ago
Well written

I really enjoyed the story.

mrotismrotisalmost 3 years ago

A very well-written and compelling story. Five stars!

tkh3nkey2110tkh3nkey2110about 3 years ago

This is a really great story. A fun look into the world of male escorts. However, I wonder if one training session would have been enough to prepare an inexperienced young man for his first client? He was lucky to have drawn a client that had never gone down this road before. She didn't know what to expect. Again, a great story and a fun read.

AnonymousAnonymousover 5 years ago
5 STARS

This well-written Pt. 01 combined two of my interests -- sex education (only lightly here) and sex for pay. Also had respect with desire to bring pleasure (rather than pain, awkwardness or humiliation). I do not care for BDSM -- not understanding even the attraction of spanking. Anal I can tolerate, but often skip stories where it is advertised beforehand.

This story is great sex-for-pay, although I somewhat prefer it less formal, eg. offering a needy friend money or offering car repair to destitute co-ed, etc.

A great sex education story, that unfortunately not many have discovered is Educating Dustin Rhodes a beautiful 3 part series by Mindventure.

I noticed that The Big Bopper has more stories on his Submissions page that appear to meet these same two interests of mine. I intend to investigate.

With appreciation,

Paul in Oklahoma

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