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I was staying with Aunt Jen for three days while my parents went to Scotland for the funeral of Uncle Jack. "Aunt Jen" as I had always known her was not actually my aunt but Mum's friend Jennifer, but she had always been known as Aunt Jen for as long as I could remember.
Aunt Jen was in her mid forties and worked as a nurse, quite ordinarily but nice, although I think she had struggled financially since her husband died she was always very smartly dressed and always seemed to be wearing stockings I remember. Her and her husband had never had children and she now lived alone about five miles from us in a small terraced cottage in a village.
It was at the end of a period of about 3 weeks that I had been off school with measles so there was much discussion about what to do about me. In the end it was decided I would stay with Aunt Jen for the three days while my parents were away. This was no problem at all for me, I had always liked Aunt Jen and often confided in her about things that I wouldn't have even told my parents that was the sort of person she was, you just felt you could tell her or ask her anything.
I guess if the word had been in existence then I would have been called a "nerd", I wasn't particularly interested in sport and usually had my head in a book and the few friends I did have were similar. As regards sex my knowledge was sketchy to say the least, most of the friends I did have hadn't really discovered it yet and the couple that had seemed pretty confused about who did what to whom and with what!. At the time I hadn't even started to masturbate or "wank" as my friends called it, although for about the last month I had been getting erections, sometimes at quite embarrassing and inconvenient times.
Being an old cottage with no central heating Aunt Jens house was not the warmest place in the world in winter, there was a really nice big coal fire in the sitting room but the only other heating was a portable electric heater which she moved around the house as needed. The bedrooms were as cold as ice, Aunt Jen had put the heater in my room for an hour then in hers but by the time I went to bed to me it was still freezing cold in my room.
Aunt Jen then suggested that maybe she should leave the heater on in her room over night and that I sleep in her bed with her. You can probably tell my lack of knowledge about sex when I say didn't even give this suggestion a second thought, it just seemed a practical and very sensible way of both of us keeping warm on what was a very cold winter night.
I was sent to bed about 9 and I was still awake when Aunt Jen came to bed around 10.30. She had already changes into her pyjamas, thick dark pink pyjamas and not in the least bit sexy buy I still remember thinking how nice she looked. I am not sure what caused it but not long she had climbed in bed beside me I found I had an erection that just would not go away, because of this I was restless and kept fidgeting. This kept Aunt Jen awake and she kept asking me what was the matter and telling me to lie still and get to sleep, but it just wasn't working and the end she got really annoyed and suddenly turned over and grabbed me to shake me or prod me or something but unfortunately it was dark and her had landed right on my erection.
"Oh my god!, what is that" she said in horror
I think if the light had had been on she would have seen me turn the colour of a very ripe tomato!
"You'd better go to the bathroom and take care of that I think don't you, so we can both get some sleep" she finally said.
I didn't have a clue what she meant and this very soon dawned on her.
"Don't you ever ermmmm . . . play with yourself" she said struggling to find the right words.
By now she had put the bedside lamp on and could see my embarrassed but totally blank look, after a few more pertinent questions she began to realise that my parents nor anybody else had never told me the "facts of life" as it was called then.
"I think there's a few things you need to know and I guess its going to have to be me to tell you. . ." she started.
She then proceeded for the next twenty minutes or so to give me a mini sex lesson, she then decided it was getting late and maybe we should continue this in the morning. . . glancing down she then noticed from the tenting effect in my pyjamas I still had my "little problem" as she referred to it.
"Jesus!, - what does it take to make that thing go down" she exclaimed.
I then noticed she herself looked rather flushed also and had a rather funny look in her eyes. . . she then learned over and with her hand on my penis through my pyjamas and gave it a little squeeze, it was as if I had been given a electric shock, nobody had ever touched me there before.
"Sorry did that hurt" she asked seeing the look of shock on my face.
"No, it was OK really" I said struggling to find words but not wanting to actually admit I liked her touching me.
"You're certainly a big lad aren't you". . . she said smiling with her hand still resting on the bulge in my pyjamas.
"Did you understand what I was telling you earlier, about men and women and how babies are made" she continued.
"Well. . . some of it" I replied.
"So do you know how to make that hardness go away now"
There was a whole load of stuff to take in from what she had been telling me and I had a whole lot of questions to ask, which I was planning to ask when we continued the conversation in the morning so I answered quite truthfully saying "Not really".
If. . . you give me your solemn promise never ever to tell anybody would you like me to help you make that go down and actually show you just what I've been talking about"
I really didn't have too much idea just what she meant by that but rather sheepishly I said accepted the offer.
She then made me promise never to tell a living sole or we would both be in a huge amount of trouble and also if at any point I wanted to stop what was going to happen I should just say so immediately and it would never be mentioned again. I promised and agreed to these conditions even though I didn't really know what was going to happen.
"Just take your pyjama trousers off. . ."
I did as I was asked, then saw she also was removing her pyjama trousers also and then tossed them on the floor by the side of the bed.
She then learned over and gave me a little kiss on my forehead and then rolled over and lay on her back. I didn't know what was going on here but I did know my penis was as hard as an iron bar and I could feel my heart pounding in my chest. Once again she asked me if I was OK and did I still wanted to continue, I answered yes.
"Come over here and lay on top of me"
I did as was asked, the smell of her perfume and the touch of her skin making my penis throb against her inner thigh.
"So. . . do you remember what I told you, and how the man puts his penis inside the women to make them both feel nice" she asked.
"Well. . . that's what we are going to do" she continued.
My penis felt like it was now rubbing up against a soft brush between Aunt Jens legs, I could see nothing because everything was hidden by the bed clothes but that's just how it felt.
She must have realised nothing was going happen if she didn't take charge so she took my penis in her hand, rubbed it up and down that soft brush for a few moments, then still holding me pressed the head of my penis into what felt like a very warm and wet groove. Once again she asked if I was OK before proceeding, I nodded.
"Now just very slowly and gently push it in" she instructed.
I willingly did as I was told and pushed the head in a little further, I remembered gasping at the wonderful feeling and seeing Aunt Jen looking very flushed but smiling.
It felt wonderful and I remember thinking so this must be it, the head of my penis was meant to fit in this little wet groove I guess and that's what sex is all about.
"Just relax a little for a minute then push it in more, but slowly, and don't worry whatever you feel in your penis is what you are supposed to feel" she continued.
Although that didn't make much sense at the time it was kind of comforting. The only light was from a lamp on the side of the bed but I could see Aunt Jen seemed to still have that far away look in her eyes and in between giving instructions seemed to be quietly making ohhs and ahhs under her breath.
I pushed a little more and Aunt Jen winced slightly, but nothing seemed to happen it didn't seem to want to go any further in.
"Sorry, but it won't go in anymore" I said disappointed.
"I think you are just at the wrong angle, move down a little"
I lifted myself up a little and did as she suggested carefully making sure I did not become dislodged, then eased forward once again. . . it was suddenly as though the gates of heaven had opened up as the whole length of my penis slid all the way inside. If had ever masturbated I might have just been a little more prepared, but I hadn't even done that at that time so nothing prepared me for the beautiful and intense feelings in my penis. I think I must have moaned or groaned with sensory overload because once again she asked if I was OK.
The best I could offer under the circumstances was a rather pathetic "Yes, it's wonderful, it feels wonderful. . ."
"Well it's going to get even better very soon but lie still now, lie still just for a minute or so and try to relax" Aunt Jen instructed in between small gasps of breath.
Although I was doing as she asked and not moving my penis just seemed to have a life of its own and gently throb within the tight confines of her vagina. I am not sure whether Aunt Jen had good muscle control or whether she was just very tight because she had never had children but her vagina seemed to fit my penis perfectly, and I was not large by any means. It felt like a warm, wet, well fitting tight glove, at that time I had no other point of reference or comparison but it felt like pure bliss, it was just heaven.
I just laid there between her legs embedded inside her but not moving exactly as she had told me, to be honest as stupid as it sounds I don't think I even knew I had to move. If I had listened to Aunt Jen's little talk earlier a bit more attentively maybe I would have had a better idea but there was just so much info to take in especially when such a lot of contradicted the stories that school friends had been telling me about "how you do it".
"Are you OK, Do you still want to carry on" she asked.
I was certainly OK but didn't know really what "carrying on" meant, wasn't this it. . . I nodded again but then when I didn't do anything else I think she sensed more instructions were going to be needed.
"In a minute I want you to start slowly moving . . . slowly moving in and out, but not quite all the way out. . . it will feel really nice, the more you do it the stronger the feelings will get and the nicer it will feel" she explained.
This was certainly sex education at its most basic, but at that moment this was all the information I needed.
"The feelings will get stronger and stronger and then finally you will climax, then maybe some white fluid will come out of your penis, but its normal, its OK, if you take it slowly it makes it last longer and then its nicer for both of use" she continued.
I think at that point we both knew the instructions now had to stop and we needed to really do this.
I tentatively started to slowly push in and out; the feelings were both incredible and beautiful. This was the best feeling ever, it was heavenly. . . It's strange how things go through your mind but I remember thinking it felt so tight maybe this is hurting Aunt Jen but at that moment any fears I had were allayed. . .
"ohhhhhhh that's so nice, we are just a perfect fit . . . that's it keep doing what you are doing, push it in and out make it feel good. . . yes, yes, that's it you are doing good"
Clearly Aunt Jen was feeling similar feelings to me.
The exquisite feelings seemed to intensify with every in and out movement. The tightness, the heat and slipperiness of her vagina increasing the wonderful sensations in my penis with every thrust.
I was now relaxing a little and letting my feelings and nature take over, but it was fast getting to stage where I really don't think I could have stopped even if I had wanted to. The pleasure from the sensations in my penis was building and building and becoming overwhelming, I think I had began to moan and even whimper a little now with ever thrust . . . I remembered what Aunt Jen said about it feeling better and better but thought surely it can't get any more intense. . .
The whole of my being seemed to be centred on my penis and the constant in and out movement, nothing else seemed to matter, all nervousness and uncertainly now gone, I was totally lost in pure physical pleasure. Aunt Jen was now moaning and pushing her hips up to meet my every thrust and like me finding it difficult to speak, I was fast losing control and finding despite every effort to slow down was in fact pushing in and out faster and faster.
"That's it, yes , yes keep going, cum inside me" she gasped.
I had no idea what she meant but I knew something was building up and up and I couldn't stop it even if I wanted to, I was groaning and moaning and my hips seemed to have a life of their own. . . Aunt Jen then wrapped her legs around me and held me tight, my movements were now considerably restricted, in fact I could hardly move she had such a tight grip on me. At the same time I could feel her internal muscles working hard gripping and massaging my penis. I finally let out a loud groan and then a yell and thought I was going to pass out from the sheer intensity of the feelings as my first orgasm hit and spurt after spurt of sperm shot from my penis. Aunt Jen held me tight as my orgasm slowly subsided and we both basked in the afterglow. I don't think Aunt Jen actually came but it was not something I knew about or was in any state to think about at the time. It had taken less than five minutes for me to orgasm so I sure that was not really long enough to satisfy her or bring here to orgasm.
Aunt Jen asked me if I was OK again, I was OK but I was finding it a little difficult to coherently put together much of a reply, I was still reeling from the totally wonderful and incredible experience I had just had.
I was awake early, by head still full of what had happened the night before and also supporting a with very healthy erection that once again would not go down and allow me to go back to sleep. Neither of us had put our pyjama bottoms back on so as I cuddled up to Aunt Jens back my penis was rubbing against her bottom and just making matters even worse. I tried not to rub up against here, not wanting to wake her but the lovely feelings as I brushed up again here with my penis were just too nice to resist. It was wasn't long before I began to notice she was pushing back against me slowly but rhythmically, she didn't speak and I couldn't see her face but obviously she was now awake.
This went on for some time before she very quietly said "Would you like to do it again"
That question hardy needed an answer, I couldn't wait.
To my surprise she then got out of bed saying she would be back in minute, she came back into the bedroom holding what looked like a packet of bubble gum and saying something about it being old but should be OK. I was puzzled.
"I'm guessing you haven't used or even seen one of these before so shall I put it on for you"
Since I did not know what it was she was talking about I thought it best to agree.
Aunt Jen, tore open the little packet, instead of bubble gum it contained what looked some sort of rubber ring. As she pulled back the bed clothes to get access to my erection she explained what it was.
"This will keep the sperm from going inside me and also perhaps reduce the strength of the feelings a little for you and make it last longer"
She then proceeded to role the condom over my the head of my penis and all the way down its length until it was finally fully encased in the tight clinging rubber. I remember thinking how strange it looked with the little bubble of rubber on the top ,it did not dawn on me what this was for. It felt strange but somehow erotic, but by now all I could think about was how much I wanted to be inside her and experience the wonderful feelings like last night all over again. Aunt Jen climbed back into bed but instead of laying on her back laid on her side with her back to me as she had done when she was asleep earlier.
Before I could say anything else she pushed back so my penis was nudging between the cheeks of her bottom, clearly she thought I was not going to be able to find my own way, so she took me in her hand and guided me to where I should be. . .
"That's it just there, now push it in. . ." she explained.
This time I didn't need any more instructions, with very little effort I gently sank my whole length all the way up inside her, even through the condom I could feel the heat, combined with the slippery tightness once again it felt like pure heaven.
"Mmmmmmmm that's lovely, now come on push it in and out but take slow, make it last" she continued.
I slowly started the now familiar in and out movements, those lovely feelings started to increase again as I began to get into a rhythm - in out, in out, in out . . .
To start with I thought maybe she was right, with the condom on it did reduce the feelings, but as I continued to push in and out the waves of pleasure began to wash over me and increase in intensity with every thrust. I was now unconsciously moaning and groaning. . .
"Hmmmmmm feels good eh"
I was now beyond being able to formulate any reply to this.
I wasn't long before Aunt Jen began to start moaning too. . . as the feelings of intense pleasure started to build and build for both of us. I started to pump in and out faster and faster, holding on to her hips until she suddenly cried out. . .
"Oh god!, oh my god, please don't stop . . . I'm cumming!!!!!!!!!!!!!"
Her frantic bucking and movements made me lose any control I had and felt my orgasm start, I too yelled as I felt her vagina contracting around my penis as though it was milking me making me pump steam after stream of sperm into the condom.
Over the next few days we repeated these events five or more times in some different positions, all of which were totally mind-blowing, I had never known or guessed anything could feel so good. I will never forget those three days with Aunt Jen when she took me to sexual heaven; I have never had a experiences of such intensity and probably never will again.
When I finally went back to school, friends were constantly talking about what it would be like to actually "do it" with a girl or women and how it would feel. They had no idea; and there was so much I could have told them but I knew I could never say anything and I always kept that promise I made to Aunt Jen.
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- Story Details and Information
- A few days with Aunt Jen
- Published: Jul 3, 2009
- Author: Reggie
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- Category: First time sex story
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About: "then still holding me pressed the head of my penis into what felt like a very warm and wet groove"
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