One dreamy summer afternoon, after a lovely lunch, lounging on the patio of Jean’s house , about six of us were savouring a few glasses of plonk discussing bringing up our kids and the challenges that task presented. Jean, took courage from the wine and brought up the very naughty story of the oldest son of one of her neighbours, and how she and her friends helped to resolve the situation.
My story is from the 1950s. Janet, a friend, who lived not far from me on a local authority housing estate, asked me for help.
Our houses were similar, so you get the picture. Three bedrooms, bathroom, separate toilet, kitchen, small lounge and similar dining room. Adjoining the house and outside we had a utility shed, a coal shed, the houses were heated on solid fuel, and an outside toilet which was directly opposite the kitchen or “back” door. The “front” door was rarely used except for “best”.
We all had kids of similar ages, my daughter Christine, was eighteen, I also had a younger son. I was widowed a few years ago, and without friends, where would I have been?
Anyway, Janet came to me with her problem. Her oldest lad, Jack, a class mate of my Chris, she was shocked to find, had a substantial cock she said, and she felt without proper guidance could get himself into “trouble”.
I had also heard about this cock from Norma, another neighbour who had seen it when she looked into a garden shed and saw Jack with it in his hand, obviously enjoying himself.
Norma’s comment was she wished it had been in her, never mind her hand! I was curious particularly as I had seen him and my Chris behind the shed with his hand up her jumper, and I didn’t want Chris to get into “trouble”.
Heck, I was also keen to see what both his mother and Norma considered a “substantial cock”. Janet wanted to know what could be done and if I could help.
Between us we hatched a plot. It was the school summer holidays. I sent my kids to their grandmothers for a holiday.
Chris didn’t want to go but I persuaded her that the seaside town I grew up in would be good fun. Jack was to be sent round to my house to give me a hand, and I would give him a bit of “education”.
It was about ten on the Monday morning when he knocked on my back door, the door was open, it always was, but he was quite a polite lad and would not enter unbidden. Not getting an answer, he knocked again and yet again when still there was no answer.
At the fourth knock, I opened the outside toilet door behind him and as he turned I stood and wiped my self having just been having a pee.
He went the deep red of beetroot and turned to run.
“I thought you were supposed to be giving me a hand” I said as I pulled up my loose legged knickers.
“Mum will want me to do something” he was backing away towards my garden gate.
“No, she sent you to give me a hand.”
“She will be annoyed if she knows I saw you on the toilet.”
“Well don’t tell her then, provided you help me out, I won’t tell her.”
I stepped into the house and got him to follow me. I closed the door behind me, he looked panic stricken. Doors were always left open in our neighbourhood during the day.
“Don’t worry, I won’t bite. Well not just now anyway. You and I have to have a little chat.”
Again he went red. I lead him into the dining room, it was at the back of the house and not overlooked.
I sat in a small fireside chair and called him to sit on the arm. I put my left arm around his waist and pulled him closer. I knew my breast was pressing into him but pretended not to notice. He was wearing shorts, and I could see a tent in them.
“What’s this then” I asked placing my hand on his leg just above the knee. He didn’t answer.
I slipped my hand up the leg of his shorts and touched his cock. He tried to pull away but I had him firmly.
Now girls, as you know, it’s not polite to talk about size but we generally do and they say, well, we say, size isn’t everything. I’m going to tell you this now. I had several cocks before I had my Bob and one or two since, but by Christ, never in my life, and to this day did I have another one this size.
His mother had only seen it slack, and she said it was like a young donkey, well I had never seen a young donkey’s cock and Norma, she said he had it in his hand and she wished etc. Well, I HAD it in MY hand and I could have wet myself.
“Now then” I had hold of his cock, “I want to know what you were doing behind the shed with my Chris?”
His cock deflated, “I…I… We…”
“Don’t lie to me, I saw you with your hand up under her jumper.” I squeezed his cock gently and it slowly came back to life.
“We didn’t do anything, honest.”
“You were feeling her tits weren’t you?”
He hung his head.
“Yes.” He muttered.
“We have got to sort this business out. We can you know, But I must have your promise, you are not in any trouble, but I really must have your promise 100% you tell no one about this. No one at all. Do I make myself absolutely clear? If anyone is to know then I and I alone will tell them what they need to know.”
“What do you think your mother would say if she knew about your antics?”
He didn’t answer.
“Do I have that promise.”
“Come on, say it. Say ‘I promise I will never ever tell anyone about anything about today or any other day unless I am told I can by you.!”
“Say all of it.”
He did so.
“If I ever hear a word about what we talk about today from anyone, and I mean anyone, your life will be changed for ever!”
I pulled his hand onto my tits, over my summer dress.
“If you like tits, have a feel of these.”
As soon as I released my grip his hand shot away so fast it almost broke the sound barrier.
“What’s wrong with my tits then? Why don’t you feel them like you do Chris’s?”
“You’re a lady.”
“Yes. So what’s wrong?”
“You shouldn’t touch lady’s tits because it’s rude. With girls it’s different. They like it.”
I pulled his hand back to my tits, “So do ladies!”
“Am I getting a bollocking for feeling Chris’s tits?”
“No, it’s quite natural for boys to want to feel girl’s tits, and if she doesn’t mind I don’t mind you feeling Chris’s.”
Personally I think Bob would have been more bothered about me letting him feel mine than if he caught Jack feeling Chris’s tits. But Bob was gone and I was feeling horny and Janet wanted a hand with her problem.
As Jack relaxed a bit he started to feel my tits, squeezing them.
“Why don’t you undo a button and feel them inside my dress, like you do with Chris?”
I knew what today was to bring and I had dressed accordingly. A button through dress, high collar, no cleavage showing. I wanted to be in control.
“Do you mean I can?”
“Oh well, I suppose if you really want to I had better let you.”
(Ooh the hardship of it).
Jack started to fumble with the buttons of my dress, and tentatively put his hand inside, naively and very very gently he stroked and squeezed me through my bra.
“See, ladies are only big girls, they like just the same things. Do my tits feel like Chris’s?”
“Well, sort of, but sort of softer.”
“Have you felt inside her bra?”
“No, she said we mustn’t.”
“Hermmm… That means you tried!”
“But I didn’t… She said we mustn’t.”
“Why did she say you mustn’t go inside her bra?”
“She said it was rude and we might get into trouble if she let me.”
“Why did you want to?”
“I don’t know…Other chaps say they do it to their girls friends, but she got cross when I wanted to… so I didn’t.”
“Did you do it another time?”
“I tried but she said if I tried again we would have to stop playing with each other. So I didn’t.”
“Do you want to now?”
“If you don’t say its rude, and I can’t be here any more.”
“Well alright then. But you must remember the promise not to tell anyone, even Chris…ok?”
Jack nodded then put his hand into my bra.
(Plain white, the old fashioned cotton type, not very elastic, I expect you girls remember the ones I mean.)
The cups were over full, with both my tits and Jacks hand in them. The seams were straining, I could hear and feel them. He was clearly enjoying the feel he was getting and to be honest, so was I.
My hand was still gripping his cock up the leg of his shorts, he seemed to be getting harder as he played with my tits, he put what I remember of my Bob in the shade, which wasn’t bad for a late teen.
Anyway, as I say, he was enjoying the feel he was getting of my tits, sort of as a reward, each time he touched my nipple I gave his cock a little squeeze. It kept him at a good size and worth holding.
Things had to progress of course. The way I was thinking was that if I played my cards right, I could resolve Janet’s problem, make sure my Chris was ok, and maybe do myself a favour too.
“Are you enjoying that?” I smiled at Jack.
“Is it like you expected when you tried to do it with Chris?”
“So what is different?”
“Well its skin isn’t it, and they are bigger and softer.”
“Get your hand out.” Jack’s cock went slack in my hand. Sharply whipping his hand from my breast.
“Don’t worry, we just need to go into the other room.”
I led him though to the lounge, by the cock which was sticking out of the leg of his shorts, by the time we got through the door I had coaxed it back to its former rigidity.
“Has Chris ever held this?” I gave his cock a little stroke.
“N..N..No.” he mumbled.
“I can tell you are lying. Just don’t tell me lies”
“Has Chris ever held your cock?.”
“And, what did she do with it?”
“She rubbed it?
“Why did she do that?”
“Because I asked her to. She was holding me and I asked her to because it felt good.”
“She had her hand inside your trousers?”
“She had my cock out of my trousers.”
“And what happened?”
“Nothing, honest, she just rubbed it a bit and it felt good. Guys I know says it is wanking and you can get stuff out if your girlfriend rubs it.”
“Take your trousers off.”
I sat in a big comfy easy chair with my back to the bay window, we couldn’t be seen through the nets, and instead of resting back into it, I sat to the front with my legs spread, the wide skirt of my dress fell between them,
(I am sure you remember those dresses, you could conceal so much beneath them.)
I positioned Jack in front of me, then pulled the skirt up to rest above my knees. His cock was like a flag pole, tall and straight.
“I think young Jack that you should undo my bra, don’t you? Just lean against me, reach round behind and undo the clip.”
He did poor lamb, well he tried, he slipped his arms around me inside the open top of my dress, his cock resting on my tits and fumbled at the back. I ended up giving him a hand, getting him to feel the clip, then helping him undo it.
(You know as well as I do girls, just how sexy it can be, helping inexperienced hands to undo your bra!)
As my bra came away he sat back on the floor, of course, he was then looking straight up my skirt.
“What are you looking at.”
“Believe me Jack, what you are looking at is not ‘nothing’!”
“I didn’t mean to look.”
I pulled my skirt over his head as he struggled to get out. I let him escape. He sat red faced in front of me.
“Have you put your hand up Chris’s skirt?” I knew he had, I had watched from behind the curtains in the bedroom.
“Is that true?”
“I think that’s a lie! And I don’t want to tell your mum that you tell lies.”
“Have you put your hand up Chris’s skirt?”
“See, it wasn’t that difficult to tell the truth was it? Why did you do it?”
“What did you find up there?”
“What were they like?”
“Sort of soft and warm.”
I recognised, as I know all of you will, the description of the old type of school knickers, warm and fluffy inside and smooth and soft outside, Chris’s were regulation school navy blue.
“Put your hand up my skirt.”
Jack appeared frozen, like a rabbit caught in headlights, the expression of panic in his face was a picture.
“Well come on, put your hand up my skirt, you can already see what’s up there, there’s nothing to be afraid of, feel what my knickers are like.”
His hand shook so much as it started to reach for my knickers, it looked as if he was waving to someone.
“Well? What are they like? What do you feel?”
“They are silky smooth, and there is no elastic in the leg.”
“Have you put your hands inside Chris’s knickers.”
Suddenly he was bolder.
“Yes, it was warm and sticky and a few hairs.”
“Well now do the same with me.”
He did as I bid, and touched me.
“It feels wet, and there is quite a lot more hair. ”
I was breathing quite heavy and it wasn’t easy to talk normally.
“Well you have a bit of a feel around and see what it feels like properly.”
“It’s ever so smooth isn’t it, and so soft…apart from this little bit here.”
He touched my clit. I nearly knocked him over I jumped so. Poor lad.
“Have I hurt you?” Jack was most concerned.
“No, no dear, I just like that bit specially.”
He touched it a bit more, until I came off and clamped my legs together.
“There you are, see, that happened because I really liked what you did.”
I spread my legs and encouraged him to continue.
“You only need one hand down there.”
I took the other hand and pulled it back to my tits. He squeezed me hard.
“Gently!” I reminded him.
“There’s a hole down here, is it your bottom.” He was probing deliciously into it.
“No dear, if you take your fingers out of there, and go just a bit further back you will find my bottom, it might be a bit crinkly,” I still had that stiff young cock in my hand.
“Oh yes. I have found it. Should I put my fingers in there?”
“Well not just now dear, maybe another time.”
I had a ‘thing’ about my arse being touched. I just didn’t like it.
“I think before we do any more that maybe we should lie on the floor.”
We lay together on the rug. On our sides, face to face.
“Now, when you lie with a lady, you touch her to make her feel special, you know about touching tits, and if you lean over you can lick them and suck them.”
“Urgh.” Was the unexpected response. “That’s what babies do and get milk. Yuk!”
“Well you don’t get milk when you lick and suck a lady’s tits when you are doing this sort of thing.”
Jack looked very sceptical. But fair do, he tentatively snaked out his tongue, gently tickling the tip of first one then the other rigid nipple. Not tasting anything he didn’t like, proceeded to suckle on them.
I expect you girls can imagine how difficult it is to breathe and instruct with a pair of young inexperienced lips and a tongue servicing your tits, and mine had not been serviced like that in years.
“Very good.” I encouraged, “See, nothing unpleasant about that is there?”
I took his hand to the hem of my dress.
“Now, instead of going straight up to my knickers, you already know what you will find there, you must do it the right way, the way most ladies like, you must slowly stroke your way up to my knickers stroking my legs as you go.”
He started his way and I was wetting myself with desire, trembling with lust, trying not to proceed too fast and that was such a job. He did as he was asked and at last, probably in a couple of minutes he was at my knickers again then at the soft skin above my stockings.
I took his hand back down to the hem of the dress again.
“Now this time, as you move up along my legs, not forgetting the stroking, I want you to unbutton my dress. Do you think you can manage that?”
This time when he got to the naked bit above the stockings I urged him to continue as he had the first time he put his hands up under my skirt.
He did so, finding all the wet parts of me, finding the little hard bit that had made me jump so the first time he touched it, and finding again the soft part he had previously found.
“Now my dear, I want you to take my knickers off me.”
” What right off?”
“Yes dear, right off.”
He knelt up beside me and pulled the waist of my knickers down, I lifted so he could get them over my bum, then encouraged him to tease them from my wet slit. He lay back down with them in his hand.
“You know how you found that spot that you thought was a hole?”
” We need to find out how deep it is.” I had a good hold on his cock. “this is what we will use.”
I eased him over to lie between my legs. Every touch was making me cream, and his position there was no exception.
“You take hold of your cock and see if you can find the spot again. If it is a hole we need to find how deep it is.”
The knob on the end of this cock girls, was, as they say these days, ‘to die for’.(like big firm plum!)
“Is it nice and slippery there? Good, good, now rub the end of your cock from the front bit back towards my bottom, and see if you can find that hole.”
He found it! The knob slipped in. It had been a while since I had one so it was quite snug. It popped back out.
“Yes, I’ve found it. isn’t it soft and smooth? “
“Right, very good. Now to find how deep it is. Slip your cock back in.”
He did so.
“Now as far in as you can go.”
“Is that far enough?”
“Come right back to the start and try again.”
“That feels very nice.”
“Yes doesn’t it.”
“Can I do that again?”
“Sure, As often as you like.”
He took to it like a duck to water, gradually nature took over, and he was riding like an experienced jockey. Suddenly he stopped. I had been coming for a while, I was saturated.
“What did you stop for?”
“It felt like something came out of my cock.”
“Yes it certainly did. That’s what is supposed to happen.”
“Should I take it out?”
“No, don’t bother, I expect it will come out on its own soon.”
Together we just lay there in the after glow, a warm feeling of contentment swept over me, the like of which I hadn’t felt since I lost my Bob. I hugged that lad to me. Waiting for, not wanting him to drop out of me.
“You do know, young Jack, don’t you, and pay attention. Its important, this is not something you should do with young girls like my Chris. You should only do it with older ladies.”
“But it is so nice, it feels so… nice when stuff comes out.”
“Stuff coming out isn’t the problem, it’s what that stuff can do that is the problem.”
“What does it do besides feeling nice?”
” It makes babies, that’s what.”
I was still waiting for that cock to slip out of me.
“So are you going to have a baby now.”
“No, I’m not, and I don’t want my Chris to either. That’s why I say, it’s not something you should do with young girls.”
“If you want to do it, come and see me, or use your hand, and I know you have done that.”
“Can I do it again now?”
“Yes if you want to.”
“Can I push it in and out or do I have to do it with my hand.”
“Which would you rather?”
“Push it in and out.”
“Well there are other things you need to learn too, so for now pull it out.”
The darned thing was still rock solid, and I needed a breather! I got a clean pair of knickers, this time bloomers, and slipped them on and straightened my nylons.
“Thing is, when we started today, you squeezed my tits and licked them, then you put your hand up my skirt and felt my knickers, then you found how it was wet up there, and you found the soft hole, and then you checked the depth.”
“Now you have to put it all together, and just like with Chris, you have to start with kissing.”
“Kissing?” he looked horrified.
“Yes kissing, just like you do with Chris, but you might find it better. So come here and kiss me.”
He did so, reluctantly to start with I must say, hard tight lips clamped hard together. However after a few… not too sloppy… he did accept kissing as an essential part of the pleasure he had been having. I moved his hand to my tits, and after short while, urged him to return to my nether regions.
He felt the satiny fabric of my knickers, then the elastic round the leg just above my knee. Stroking, he did not bother to try to intrude beneath the elastic, but caressed, with my encouragement to the gusset where he stimulated me outside the knickers, the satiny fabric assisting his endeavours. Eventually I could stand it no longer, I was desperate to have his young hands on me not just on my knickers.
I took his hand and lead it back to my knee.
“Very good, but now go under the elastic.”
He did so, spending much time just caressing my stockinged thighs.
“Like this?” He asked.
He reached the top of my stockings, the texture changed and I could feel it. We were kissing again, but Jack kept breaking off to see what he was doing. His hand of course hidden inside the leg of my knickers. His fingers touched flesh, oh the tingle. Do you know girls, I can feel that touch right now as we talk..
“I think its time to get those knickers out of the way, don’t you?”
“They are a bit like Chris’s but a lot bigger.”
He withdrew his hand and proceeded to separate me from my modesty, not that modesty was my principle concern. I raised my backside to assist him, and soon they were discarded beside us. He had learned well and was soon back in contact with my juicy, and very hungry hole.
I assisted him to get himself between my willingly parted thighs, he homed in on my hole and was in it to his balls in a moment. That triggered a vigorous cum… I didn’t know they were called orgasms until years later… I had to hold back a bit or I would have thrown him off and that was the last thing I wanted.
“When you think something’s going to come out of you, tell me.”
He rode me as if his life depended on it. It seemed a long time before …
“I thinks its going to go off in a minute.”
“Then you had best play with my tits and kiss me then hadn’t you.”
He did both and it hit us, I knew he had cum because his groan was smothered by my mouth. He must have known it had done something for me as I clasped my legs around him.
“Now are you going to have a baby? I don’t want you to have a baby.”
“No Jack, young ones have babies, that’s why I said to you to come and see me if you really need to do this, or to use your hand.”
He continued pumping in and out, and once again I found myself waiting for him to slacken and come out. After about half an hour, having had several more cums as he still lay inside me, rocking back and fore and with no indication of him slackening I decided to call it a day and got him to pull out.
“Oooooh, do I have to? It’s nice in there and I want another go.”
“How quickly will it go if I say yes?”
“I can try to make it go quickly.” His eyes pleaded.
“Oh alright, go on then, have another go, but be quick, I can’t lie here all afternoon.”
To be honest girls, I do love my nooky, but this young chap was becoming more than I could cope with, I was bloody knackered. What had I let myself in for? The vigour of it. You know how it is, much as you’re enjoying it there comes a time when you start to feel raw, sort of chaffed, and it’s nothing to do with being wet enough.
He slipped it in again, and I started to lose it. What I mean, I started to come as soon as he entered. I have to admit to being relieved when he said it was just going to go off. As he spewed deep into me I just knew I was going to need help to cope with him. Don’t get me wrong, I enjoyed every one of those fucks, every come I had was appreciated but it had been a while. Right then I felt well used. I had forgotten how much come was stored up in a pair of young balls.
“That’s it now, get yourself dressed, and tell your mam I want to see her.”
“Am I in trouble?”
“No, but cut along home, and come back to me tomorrow about half nine.”
“Does that mean I can have another go?”
God, it was like a game now that he knew how to play.
“Well, I’ll think about it. I might give you a test to see what you have learned.”
I was still pulling myself together when Janet arrived at my door. I was getting a pair of knickers on and my tits were still out of my bra.
“How did it go? Is he big? Are we going to have a problem?”
“Oh it went ok, we managed. Big? Hell no, he’s not that big… he’s fuckin’ enormous. If it’s left to me, we may have a problem, I don’t know if I can cope, he fucked me about five or six times, I lost count, that was after I showed him what to do…and I have just had to chuck him out… he wanted another go!”
“So what next.”
“Thing is, I think we can keep him out of trouble, but I will need some help. I have told him to come round tomorrow so I can give him a test.”
“I am going to talk to my mother- in- law this evening, if she agrees, when you see her coming up the road, it will be about nine, come round yourself after you remind him to come round to see me at half past. You can see his cock for yourself, and mother- in- law can test him.”
My mother in law had been telling me for sometime how she missed the sex life she and Bob’s dad had. How she wished she could get a risk free share without the chance of being leaned on by friends and possibly getting a ‘reputation.’
I visited her, she lived only one street away. Took a small bottle of Port and a lemonade with me and sat and chatted. I broached the sex issue,
“Jean, I’m so bloody desperate at times, I bloody diddle myself… Its just not the same though, my old pussy needs a stiff cock, but that old candle and my fingers are a poor substitute for a bit of meat.”
“If I told you I might have a safe way of helping you out, would you be interested?”
She sat up in the chair.
I told her the story of the day, Janet’s approach, what we had decided, and how it had gone and how I couldn’t cope on my own, and the promise.
“Are you sure he wouldn’t tell? He is a bit young.”
“I’ve threatened to tell his mother, he doesn’t know she is behind all this.”
“I’ll tell you this, it might put you off though, he’s got a hell of a cock on him. I reckon it would split Chris in two if it was her first and that’s what we are trying to avoid. Well, and her or anyone else getting pregnant.”
“Bloody enormous. Bigger than my Bob, and bigger than any of the other fellows I have had before Bob or since.”
“That sounds promising.”
“I’ve told him to come to me in the morning and I am going to give him a test to see if he has learned anything today. What I think is that I will tell him to come into the room, and sit with you and you can just say to him that you heard he had a lesson yesterday, and what did he learn and he should do all the things he was taught with you because that would be his test.”