Babysitting my Toy Boy
If you want to catch up on my adventures to date, you’ll find the list of all 120 blogs here: https://medium.com/@TracyTrouble
If you want to catch up on my adventures to date, you’ll find the list of all 120 blogs here: https://medium.com/@TracyTrouble
From one end of the age spectrum to the other. Last Tuesday I spent an interesting evening in my car seducing an eighty-four-year-old. On Saturday I had the pleasure of entertaining John, my tame nineteen-year-old.
I couldn’t quite believe the phone call I received from his mother on Friday evening.
“Hi Tracy, I know this is a terrible imposition, but is there any chance you could keep an eye on John this weekend?”
“What do you mean, “keep an eye on him?”
“Well, you know mum had that fall on Thursday?”
“Yes.”
“Well, she can’t get around much and I suggested she came and stayed here for a while, but she won’t hear of it. She’s insisting she goes and stays in a care home where her sister is. That way she says she’s not a burden. She’s phoned them and organised the whole thing. The point is, it’s in Herefordshire and she needs us to take her which we’re doing tomorrow but we won’t get back until Sunday and you know how unworldly John is, I’ve left him instructions and a couple of frozen meals, but I just wondered if you could pop in to check he’s okay and hadn’t either poisoned himself or set fire to the house.”
What an opportunity!
“No problem at all, Lizzie. I’ll make sure he stays out of trouble.” Or hopefully in Trouble-Tracy Trouble.
“Oh, thanks so much. Just pop round late afternoon; make sure he’s coping.”
“Will do.”
I’m not being judgemental, and as far as I was concerned, it was a golden opportunity, but he’s nineteen! Isn’t that a bit old for a babysitter? Loads of kids are away at Uni by then, cooking and washing for themselves. Still.
I dressed for action. Nothing outlandish. A wide hemmed skirt, a blouse, and some sexy underwear.
I drove round to their house early in the afternoon. Earlier than Lizzie had suggested, but if I stayed overnight, I’d have John for eighteen hours. Life could be fun.
I rang the bell and waited. No reply. I rang again. Still nothing. I had Lizzie’s words ringing in my ears. ‘Make sure he hasn’t poisoned himself.’ He couldn’t have. Could he? I was wondering if I should call the police when I heard movement and the door opened a crack. “Oh. It’s you.”
What a welcome!
“Yes. You okay? Your mum presumably told you she asked me to look in on you?”
“Yeah, she did, but I didn’t think you’d be around till this evening.”
He was acting a little strangely, hiding his body behind the door and just poking his head around it.
“I thought you might fancy some fun, but if you don’t, then I’ll go and come back later.”
“Oh no, don’t do that! Er…” He looked down at himself. “I, er… oh, you know anyway. Come in.”
I didn’t understand what he meant by that. I went into the hallway and he closed the door. I turned to face him. He stood there in a bathrobe. A nineteen-year-old showering in the middle of the day? A question formed in my mind. Did he already have someone there? A girlfriend? A boyfriend! I’d not picked up any vibes he might be bi but I’m no expert. I asked. “Sorry, do you have a friend round?“
“No.” Back to his monosyllabic teenage self.
“So can I stay?”
“Please.” Almost a plead. Did he have urgent needs? As urgent as mine? I’ve told you he’s no hunk, but with him standing there in presumably nothing but a bathrobe, knowing he wanted to fuck me, started me leaking. I went to hug him. “You don’t mind?” he asked.
“Mind what?”
“That I’m wearing these?” He opened his bathrobe. He was naked. Apart from Lizzie’s knickers! I knew they were hers, they were the ones she had worn when we were out with Chris. Seeing this young man in a full pair of sexy white Lacy knickers was so horny.
“No. I don’t mind.” The words woke his snake up. There was movement in the knickers. They weren’t totally sheer, but the outline and shape of his cock was clear. I closed on him. Clamped my hand over his cock through the smooth material. I had eighteen hours. I wasn’t bothered if he came to my touch. With his recovery speed, he could still be getting it up another twenty times. (I know, I know!)
I closed in on his mouth. Locked lips with him. His cock had hardened and escaped from the knickers, sticking out of one leg. What a sight! They weren’t designed for containing a monster like his. Or any cock, I suppose. Having seen Geoff’s wapon so recently I could compare the two, and I had been right. My octogenarian’s was longer, but far slimmer.
My hand slid off his mother's knickers and grasped his member while our mouths continued to grind together. His tongue technique had improved dramatically over our few sessions, but wasn’t a match for Geoff’s. Perhaps I could get the old boy to give lessons.
I didn’t wank John, just held it firmly. Enjoyed the feel. After Geoff's pencil like cock, John’s girth felt extreme. I knew a wank would likely cause his eruption and now it was free, I didn’t want his cum all over Lizzie’s hall carpet. Unadulterated sex for the next eighteen hours was required, not housework cleaning up his semen. I dropped to my knees, pulled his cock towards me, and enveloped it in my mouth. The eruption was instantaneous. He must have been on the brink when I rang the doorbell. I bet he swore, but I’d make it up to him. His cum tasted good after the disappointment of my pensioner and I savoured every drop. Oh, the taste and feel of that young, vibrant penis!
Once he’d stopped pumping, I took it out of my mouth and licked it clean. Overkill perhaps. most of his semen had gone straight down my throat but he didn’t mind my continuous licks along its length, underneath, over his balls, licking his helmet like an ice cream cone. I kept going until all hardness had gone out of it. Which was some considerable time. My ministrations kept making the blood return.
When I was satisfied, I stood up. “Your turn. But let’s go somewhere more comfortable.” It had been a horny experience doing that in Lizzie’s hallway, but I had a feeling there would be a lot of bodily fluids in evidence shortly and thought just damp sheets would be easier to deal with. He led me up to his bedroom. A single bed. A desk with a computer and posters of aeroplanes over his walls. This lad needed to move on.
I turned to face him. “On your knees.” His obedience hadn’t deserted him. He looked up at me like a puppy desperate for love.
“Put your head up my skirt. Push your face against my knickers.”
The sheer lewdness. Watching him grab the hem of my skirt. The feel of his face brushing against my legs as it went up to my pussy. For no apparent reason, my mind went to my office. The thought of someone doing this under my desk. While I worked. While I had colleagues in the outer office. Perhaps…
“Rub your cheek over them. Tell me if you like the feel.”
“Yes.”
“Does it make you feel sexy?”
“Yes.”
“Come out. Stand up. Take off your mother's knickers.” He did as asked. “Give them to me.” He handed them over. There were splashes of his cum in them. If he was in a kinky enough mood to wear his mother’s underwear I decided I could push his boundaries, broaden his education. I put the lacy garment to my mouth licked and sniffed it. There was a hint of perfume so my guess was these had come out of the laundry basket. Kinkier and kinkier said Alice! “Put your hands up my skirt, pull my knickers off.” He knelt down and his hands followed where his head had gone earlier. His hands fumbled. I doubted it was nerves, more likely the sexual anticipation of what might be coming. He pushed them down to my ankles and I stepped out of them. “Now put them on.” I’d worn a black set of lingerie, lacy, with bikini-style pants. He didn’t hesitate. I could see in his face the sexual thrill it was giving him. Confirmed by his twitching cock.
Seeing my knickers worn by this teenager was doing things for me too, but I wanted to go a step further before I got him using his mouth on me. “Okay, now put these on me.” I handed him his mother's knickers. His cock was going ballistic. Such recovery speed seemed matched to the speed with which he came when touched. A law of physics, positives and negatives balance!
The action wasn’t helping me stay sane, either. This was so deviant. He drew them up my legs and pulled them into place. “Now rub me through them.” I knew I was going to cum as fast as he had. Stupid really, but the thought of wearing my friend's knickers, which her son had been wanking into not thirty minutes earlier, was such a turn on. As it was, as soon as his palm touched my pussy I felt the orgasm building. I hissed at him. “Fingers in me! NOW ! Get your head there too! Drink!” I was so wet, so ready, that even three fingers weren’t difficult to take. One thrust. Two. Three. He knelt and got his head between my parted legs. I held my skirt up to my waist. And I came. He pushed his lips against mine and did his best to lap it all up. What he missed started its run down his chest. When my torrent stopped, I pushed him onto his back on the floor, knelt over him and licked up what juice I could.
Hardly what I’d planned, but at least if there was going to be a damp patch on the carpet, it was in his bedroom rather than the hallway.
I needed more comfort. Something softer under me, so climbed off him, pulled the duvet off his bed and told him to lie down. I resumed my position sitting on his thighs. I thought he might enjoy the view. My spread legs. Skirt hiked up high. Suspenders struggling to stay attached to my stockings. His mother's knickers soaked with my juices, doing little to hide my cunt. My hand gently stroking his now recovering cock.
In case that introductory play hadn’t been kinky enough for him, I upped the ante.
His cock, while not solid, had a life of its own, unwilling to lie still. It kept twitching under my gentle strokes.
I gently wrapped my hand around its base and held it, pointing skyward. I waggled it around.
“Have you ever had it slapped?” I asked. A stupid question. I certainly hadn’t slapped it, so who else was there?
“No,” came the reply. A sort of questioning ‘No and I’m not sure I want to’ sort of response.
“Would you like to try it?”
“Alright.” Another one-word reply worthy of an entire sentence. ‘I’m not sure but everything you do turns me on, so I’ll try it, but please don’t be too harsh.’
I must admit some of my fantasies early on after my divorce, when I could again have sexual fantasies without breaking into a cold sweat or hitting the gin bottle, involved slapping cocks. With my hand. With a steel rule. With a riding crop. Clearly a fantasy punishment for the male of the species. But wince not, dear reader, I have passed that stage in my rehabilitation! Not that I wouldn’t use a crop or anything else, but only with permission!
Returning to John, I said, “Don’t worry, if you don’t enjoy it, tell me to stop.”
I started gently enough, gossamer taps with the palm of my hand. The first few were sufficient for John to send reserves of blood to his penis. It soon became solid and able to stand by itself. Which meant I could use two hands. Slap it back and forth between the two. I kept watching his face. Wondering if he’d be worried about telling me to stop. Concerned I’d be annoyed. But his expression gave no hint of that possibility. Quite the reverse. His eyes were on me. On my breasts. My tits were still encased in my bra, which in turn was still under my buttoned shirt. The way my feelings were going, a shirt I hoped wouldn’t survive the afternoon.
My punishment of his cock was now having an effect on me. I wouldn’t be able to resist using it for its designed purpose for much longer. A few more hard slaps darkened the skin several degrees and I couldn’t postpone another minute. I raised my body, shuffled forward, held his member upright and with care impaled myself on it. Sinking slowly, taking it and enjoying it millimetre by millimetre until it was home. A nail hammered into wood, or perhaps more aptly, a bolt screwed fully home. I sat quietly for a few seconds. No exploding penis. No screwed-up eyes desperate to hold on. I bent forward, putting my tits in range. He took the hint. A first for him, not needing instructions. A grope too that had improved. Not the jaws of a crocodile, nor the imitation of a feather. A firm grip. But a grip with feeling.
I risked moving. Lifting my body up. Starting to fuck him. He showed no inclination to fuck me. Too intent on feeling my tits, it seemed. Massaging them through the layers of material. He could make his own decision as to what he wanted to do there. If it kept his mind from his erection, I might get a worthwhile fuck. Selfish of me perhaps, but I needed it. My ache for a proper, long, luxurious, relaxed fuck was overpowering.
I was still fully dressed. Still wearing his mother’s knickers. It didn’t bother John. In fact, I’d swear it was an added turn-on. Seeing all my underwear and fucking me. Must have been a dream come true. Nigh on perfect. Other than me not being his mother.
My body was now parallel to his, but I didn’t lay on him. He was still kneading my tits. I was so tempted to tell him to rip my blouse off, but was certain he’d lose control down below. My fucking was now medium paced. Rhythmic. Over his full length. That he wasn’t moving was a plus. I could gauge my upward movement precisely. Bring his cock to the cave entrance but not have it flopping out. Back in the days when I enjoyed fucking it was something I hated happening. It spoiled the rhythm. Now with his inert body, I had ultimate control and used it.
The time had come. I was ready. I increased my pace. Thudding down on his body. Rising fast but shortening my rise so as to not let him escape. It was coming. I felt it. My orgasm. Building. Flexing its muscle. Desperate to escape, but teasing me. Miraculously John still held on. I didn’t. Couldn’t. A final descent. Opening the flood gates. A groan from the depths. My head went back. Almost theatrically I let out a cry, “Fuck! yes!” There was nothing false about it though. Then he was there too. For the first time, his hips thrust his cock into me. He joined in my vocals but less dramatically. He’d come. I lifted off him. Shuffled further up his body. My cunt over his mouth. “Open wide, lover boy,” I said, a smile of satisfaction on my face. His success at giving me a decent fuck hadn’t gone to his head. He still obeyed. I put my hands down, pulled my lips apart let what semen there was dribble out. Some went in his mouth. Some on his face. Not that there was much. I’d already consumed a day’s production. When the flow ceased I bent and licked his face clean then kissed him. The taste. The smell. Heaven.
Part 2 to follow
