A life changing realization...

Oh wow! More please!

Great stuff!!!

Do tell us more..........
Cuck who loves a creampie.

As I had licked her pussy and she had showed me how to do it the way she liked it, I had made her cum with just my tongue, and that made me feel good. She was very wet and seemed to be gushing from her pussy lips as I ate her out, not something I was quite expecting. She liked me to nibble her long pussy lips and pull them with my teeth, then concentrate on her "clit" which was like a little hard cock to me. She said she was “proud of her long fleshy lips” which were that way because of “all the cock she had had in her life”. I had obviously heard of this and had seen it in some mags I had borrowed from school friends, and had even now seen it on TV via the videos, but I had never had a girl let me do that to her. After I had finished, Aunt Ivy leaned over and quickly cleaned every drop of cum that was again dribbling from my cock with her mouth, after which we sat and talked as the video on the TV continued.

She asked me if I was shocked by what I had seen my parents get up to on the videos, pointing at the video on the screen. I said at first I was very shocked, especially seeing my dad wearing those clothes and being so meek in front of men much younger than he was, and all the stuff he asked them to do to mom! Aunt Ivy then took the time to explain about cuckolding, and about "sub men", which she said my dad was, and that my mom had a very high sex drive, and as such, they had agreed to an open marriage, but that my dad still wanted to be involved when my mom had other men around. She also said that my dad was probably bi-sexual as he seemed to enjoy the cock play just as much as mom did.

I went on to explain that now I had gotten over the initial shock, I was quite turned on the watch the videos, and had been jacking off to a few of them, as I had got the time and opportunity to watch them. Aunt Ivy asked if “I had seen her in any of them?” and I said I had seen one with her in. I should explain that Aunt Ivy wasn’t really my Aunt, she was a close long time friend of the family that had been around for as long as I could remember, and well, we just called her “Aunt” Ivy, and her husband was “Uncle” Joe.

She told me there were quite a few videos that had her in them, and that she had more at her home, which was in the next street over. She said I should come over and watch them with her if I liked. After about 45 minutes of talking she said she was “still horny” and said she “wanted to fuck if I was up to it?” “Aunt Ivy” I said, “I must admit I have always liked the look of you, and wondered what it would be like to see you naked, and then I saw the video! Now I am sitting here with my cock out and you want to fuck!”

She just got up and stripped off her clothes, leaving on her white lace stockings and high heeled shoes. She then removed my shirt and started nibbling my nipples and moved slowly down to my balls which she said she was “please to see were shaved”. My cock was soon ready to burst again and she said to “just flip her over and fuck her as hard as I wanted”. I said “what about condoms?” and she said “forget about them” she had it covered, and for me to “just come in her cunt as hard as I wanted”, I liked her use of the word “cunt”; it seemed so much more dirty and erotic.

I flipped her over and she helped to guide my cock into her soaking wet “cunt” and I banged away at her as hard as I could, and even then she kept screaming “harder, harder”. This went on for about 8-10 minutes and she was screaming the house down. I then said “I am going to cum” and she said “fill my fucking cunt with your stud cum”…all very graphic, and in the heat of the moment it actually spurred me on, as I grunted and powerd my cock even deeper into her “cunt”, I spurted all my cum deep into her, spurt after spurt. We stayed locked together for about a minute or two, then she said to me to “pull out and lie on the sofa...do it quickly”. I did as I was told and she immediately climbed on top of my face and sat down on my mouth and said “clean me out, eat all your cum from my cunt”. I did as I was told and I found I enjoyed it, I had really got a taste for it from my jacking off into my hand then licking it up, and seeing dad eat it on the videos, so eating it from my Aunt Ivy’s pussy was just another way of enjoying it.

She said I had “done well for my first time”, but that she would “continue my training tomorrow. Come around to my house about 6pm, and just keep an open mind and be ready to do what is asked of you, and I’ll take care of everything else”. This was all very mysterious as well as exciting, as I did not know what she had in store for me, but I knew it would be wild and even a bit daunting, but I didn’t want to miss anything…not a darn thing!

Wow, very exciting indeed. Thanks and please continue.

The care, feeding and training of a young man. I love it and can't wait for more.

Linda

popeye:

Your story just gets better and better.

Looking forward to your next posting and adventure.
Cuck who loves a creampie.

I think this is one of the best threads on CP. Keep up the great posting, it's the one I go to first to see if there's any new material.
Natural Born Cuckold
Pussy-Free For Life starting 02-26-2017, 2633 days as of 05-13-2024

A great story. Just wondering if you hooked with mom down the road. If its going to spoil your story please ignore and don't answer.

Thanks for all the comments, I'd rather not jump ahead on the story it will only spoil it for most of you. Here's the next installment...enjoy


The following day when I got up, I took particular care to shave my cock and balls, and even tried to shave around my asshole as much as I could. I wanted to turn up looking the best I could. I wore just some shorts and a T shirt, and made my way over the Aunt Ivy’s house in the next street, arriving dead on 6pm as I was told.

I just went in through the back door as was usual, and walked into the front room. In there was my Aunt and two other ladies who I did not know. They about my mom’s age, not quite as slim but not overweight at all. One had huge tits and the other was quite small. They were both dressed nicely in short skirts, and high heels, with tight blouses on, which revealed just a hint of nipple poking through the thin material. They were introduced by my Aunt as Sally and Ann, and I was introduced as her nephew, although I really am not.

Aunt Ivy told me to sit between the two older ladies and she explained that she was just “training me in the art of sex” and that although she had just started on that I had done well so far and she fully expected me to do well again today. Sally started by just gently stroking my leg and slowly going higher each time as she asked “what it was I liked to do”. I told her I liked football and tennis and that I liked swimming too. She was patient and said that was nice, but then asked “what did I like to do to girls?” I said that so far I had just kissed them, until yesterday, as I looked over to my Aunt Ivy with a sly grin on my face, and that all of this was new to me, but I was ready to learn. By this time my cock was straining in my shorts and Ann said “look at that Sally you’ve got him standing to attention!”

Both women were now focused on my tight tented shorts and Sally asked if I “liked my cock being sucked”, to which I said “yes”. At that she eased her hand inside my shorts and pulled my cock out through the leg of my shorts. Sally said I had a fine cock and spread her legs wider as she took my hand and guided up her leg to her pussy. I felt something hard, and pulled her skirt up to see that she had a big black dildo stuck inside her. She was shaved and the thing looked huge with her pussy lips spread so wide it looked impossible for it to be in there, but it was. She told me to take hold of it and fuck her with it. Telling me to pull it all the way out then push it back just as hard as I wanted. As I started doing this she was taking my cock deep into her throat and gagging on my cock. She then came up and repositioned herself on the sofa, lying back on a cushion as she told me to climb up and “fuck her mouth”.

As I got into position, Sally told Ann to take over on the dildo and “keep fucking her cunt with it”. As we were getting into position, Ann was removing her skirt, blouse and bra to reveal a pair of big tits with huge erect nipples. When she was undressed she got between Sally’s legs and started fucking her with the black dildo, and to my surprise, licking Sally’s cunt for all she was worth as the dildo pistoned in and out of her gaping cunt. While all of this was happening my Aunt Sally went out of the room and came back a little later, much to my surprise with Uncle Joe. He was naked except for a black dog collar and leash and a tight black leather harness around his cock and balls, which when I eventually got a better look at it looked so painful!

I was fucking Sally’s mouth, while she was getting dildo fucked and licked by Ann, as Aunt Ivy told Uncle Joe to sit down and watch how “even a young guy half his age could fuck better than he could”. She yanked the chain and powerd him to the floor to watch up close. Aunt Ivy had on a patent leather skirt and tight matching top, with a studded collar on, and fingerless matching gloves. She had bright red lipstick on and wore very high spiked shoes, looking like a character out of a science fiction comic book, but oh so hot. Once she had Uncle Joe where she wanted him, she came over and started rubbing my balls with her gloved hand and saying “well he’s everything I said he was isn’t he girls!”

She then told me to get up from fucking Sally’s mouth and come and eat her out. She went over to an arm chair and sat down, placing one leg over each of the arms, which revealed her great looking smooth cunt in a pair of open crotch patent leather panties, and told me to “get down on my knees and eat her out.” This I did, noting that Uncle Joe had spun around and was directly behind me as I ate out his wife’s sweet tasting cunt. It tasted a little like coconut, so I figured she was have used some lotion or something, but it was great.

The two ladies kept themselves busy with each other on the sofa, as I was getting my head pulled into Aunt Ivy’s cunt as she ground herself into my face. Then she shouted “you bitch boy, clean his ass for me” and as she held my head tight to her cunt, I felt Uncle Joe start to lick my ass. Not soft gentle licks on my cheeks, but he had his tongue right up my ass hole and was licking it like his life depended on it! He also kept moving down to my balls and keeping them well licked too. This had me just about ready to burst, and it was so new and a little scary, but at the same time my hormones were raging, and it felt just great.

Aunt Ivy then said “quick get your cock in me, I need to be fucked now”. I came up and positioned myself between her legs and she guided my cock right between her open crotch panties and said “fuck me hard just like yesterday”. I went at it just as hard as I could, fucking her like I knew she liked. I didn’t want to disappoint her in front of these other ladies. Uncle Joe continued licking my ass and balls, while Sally and Ann continued on the sofa. Then Sally came around to Uncle Joe and she had a whip in her hand from somewhere, and started whipping Joe on his ass saying “eat him you bitch, make him flood your wife’s cunt with his bull cum”. I must admit that with all of this going on, I was pretty close to cumming, and after a few more minutes I said to Aunt Ivy “I’m going to cum”. “Fuck me harder fill me up” she said as she panted and moaned under me. I grabbed her head and thrust as hard as I could and at the same time Uncle Joe seemed to go into overdrive, as I felt his tongue go all the way into my ass as I squirted jet after jet of hot cum into my Aunts cunt. There was so much cum, that as I looked down it was flooding out of her cunt and running down her asshole.

After a minute or so I eased my cock out, and sat down on the sofa, as Uncle Joe was ordered to clean my cum from Aunt Ivy’s cunt. He lapped it up for what seemed like 10 minutes, with Aunt Ivy pushing more out and telling him he wasn’t finished yet. As soon as my ass hit the sofa, Ann and Sally came over and started cleaning my cock with their tongues, getting every drop, as more leaked out, they fought to get it for themselves. This kept me hard and ready for the next round, but I was shocked at how quickly my education was progressing, but I had also gained a new level of confidence that I never thought was in me. I certainly was surprised with myself and with what kinds of friends and family I had, but I was looking forward to learning more and having lots of time to fuck and suck.

Awsome!
More please

Love this story!

WOW!! What a wild family you have.

Any chance of seeing a pic or two from any of these events?
Cuck who loves a creampie.

Popeye, I wish I was a member of your family hehe

Sorry no pics from back then. You must remember this was VHS tape days, and I never ever thought to take a camera...too focused on the fucking and sex - sorry.

Thanks for all the other comments, it really has made me who I am today.

Please continue with your story Popeye.

That first night at my Aunts was really the start of what my changed life. It became apparent to me that both my dad and uncle were cuckolds, although that word was not in general use back then, as far as I knew, they were “sissies” or “bi” is what I called them then. I needed to see my Aunt again and talk about what had happened, and what was going on, just so I knew more, as back then I still had questions I needed to be answered.

We arranged to meet for coffee one day and she explained that since her and my mom were teenagers, and before either of them married, they had been into threesomes, and “moresomes” with both men and women. They had had some pretty wild times in their younger days, and things, if anything, had only got wilder as they had got older.

My Aunt was pretty sure that if my mom found out I knew about all of this, she would be very unhappy and upset, so we both agreed that she should not be told of what was happening with my Aunt and me, which was just fine by me.

I asked her about my dad and uncle Joe being so, well, sissy, and she explained that they had not always been that way, but that they had grown into those roles by being unable to attend to the sex needs of her and my mom. She said they had “tiny cocks” and that both her and my mom needed much bigger cocks that would fulfill their needs. That then had taken them into the swinger scene, and then the rest was history.

I said I wanted to get to see some more of her lady friends if there were more, and she said “there were quite a few more still to meet”. So we left it at that, and I went back to watching more of the videos. About two days later, I got a call from my Aunt to say she was setting up a “bitch night” for her husband Joe. I asked what that was and she said “just come along and find out, I think you’ll like it”. So the next day I went along to this house that my Aunt had told me to come to, which was about a ½ mile walk from where I lived. My parents were still on vacation, but would be returning at the weekend. My Aunt told me to make sure I was smooth as the ladies like me that way.

The next night at 7pm I arrived at this house, just an ordinary looking house with a car in the drive-way. I knocked at the door and as the door opened, I was greeted by the sight of a very tall and slim woman, she must have been 6’-4” in her high heels, and she was dressed in a long see thru black night gown, high black stiletto heels, sheer black stockings and black garter belt. She had no bra on and everything was on show. She had small tits with very dark nipples which looked very hard and erect.” You must be Jack” she said, “come in”.
As I entered, my Aunt came through the adjoining door, with a leather corset on and thigh high boots and stockings. Swaying in front of her was a huge black rubber cock, and she was applying some kind of oil to it as she said, “oh hi there, come on in and sit down and make yourself comfortable”.

As I entered the room there were lamps all around the room, a camera set up on a tripod, and two other ladies dressed in outfits that were just made for sex. In the middle of the room was a type of padded table/chair, and over it was stretched my Uncle Joe. His hands and feet were tied to each corner so as he could not move. He was dressed in stockings and garter belt, and his ass was elevated so as it was on show or offer. I noticed on a table to one side was a selection of strap on dildos and hand held dildos and they all looked very aggressive and painful. My Aunt introduced me and said that I was "the resident stud for the night" and that I would be providing most of the "cum and the orgasms" for the women tonight.

She said “the bitch on the fuck table was going to provide entertainment for everyone”, but that his ass was just for the “rubber” cocks tonight. She went over and teased Joe by slapping her oiled cock on his face and saying “you want this don’t you?”. “Yes” he said “I am your slave tonight”.

My Aunt then instructed Carol, the tall lady who opened the door for me, to “gear up and take his bitch ass”. Carol then went over and took a large flesh pink, rubber strap-on dildo from the table, it must have been 10” long and as thick as my wrist, and she clipped it to her special belt around her waist. Aunt Ivy ordered me to remove my pants and “show the girls what I had brought for them”. My cock was already rock hard, it had been hard all day! But now it was dribbling some pre-cum as I pulled it out from my pants, much to the delight of the two ladies.

Aunt Ivy went up to Joe and smeared some oil on his ass and said to “Carol fuck him hard, fuck him deep, this bitch is ours tonight”. Carol positioned herself behind Joe and just slammed her cock right up his ass, he screamed the house down, but that never slowed her down one little bit, she just pounded him like a woman possessed. As this was happening one of the women was videoing the event, and the other, Debbie, came over and said “do you mind”, as she knelt down and took my entire length into her mouth, and licked my balls with her tongue, when my cock was all the way in - I didn’t know a woman could do that until then.
Over the next hour each of the women took turns in fucking Joe with a selection of large to huge rubber strap-ons, which seemed to cause him no end of pain, and I guess pleasure. Eventually they finished with him, and turned him over on the table so his face was pointing at the ceiling. I could then see he was wearing lip stick, although it had now become a little smudged. Aunt Ivy went over to him and re-applied some more lip stick – bright red – and asked him if he was ready for his next duty?

While Joe had been getting ass fucked, each of the ladies had taken turns, in between fucking Joe, to suck my balls and cock, and keep me right on the edge of coming. Eventually Aunt Ivy told Carol to “get into position” and Carol went over, and leaned over Joe so as her cunt was just above Joe’s mouth. “Now” she said “young man, get in there and show Carol what you have for her”. Carol was tall and she was stunning in her stockings and heels etc. She was, as were all the ladies, completely smooth, and she had even bigger cunt lips that my Aunt Ivy. They hung right down between her legs and were very puffy and fleshy. Ivy told Joe to “get her wet for the bull”, and he licked her heavy folds all over.

I stood behind Carol and eased my cock forward until I felt Uncle Joes tongue on my cock head. I then guided it into Carol’s cunt and sank it right down to the balls pulling her hips towards me. Once I was in, Joe was licking my balls for all he was worth, as I built up a rhythm and fucked Carol hard. As I was fucking Carol someone knocked at the door, and my Aunt brought in two more men that I did not know. But they sat down as I fucked Carol, and it did not take long for me to cum buckets into her wet warm cunt. As I pulled out, Aunt Ivy told Joe to “eat up all my cum and clean her for the next bull”.

The other two ladies were already sucking the cocks of the two men, and Ivy asked “who’s next?” One of the men jumped up and immediately went in and started fucking Carol again, who had not moved since I pulled out. This went on all night; each of us men fucked the ladies, over Joe’s mouth, each about two or three times, until we were all drained. Uncle Joe took all the cum in his mouth and looked a complete mess by the end of the night, with cum in his hair, face, and even his nose. It turned out that “Ron” and “Bill” the two other young men who arrived late, were a couple of brothers and misters that my Aunt knew from one of her other lady friends.
It was a crazy night for sure, but one I’ll never forget. Joe took everything thrown at him that night, and he obviously liked being humiliated and used as a cum bucket. Aunt Ivy said she would get me my own copy of the video and I could “start my own collection”. After we had all finished the fucking etc. we all got to talk and share a beer and learn a little bit more about this scene and who else was involved.

Just one of many nights that I had with many more that lay ahead of me then….

Oh my god! I wish I was your uncle!

I
I am sure we would have put you to good use Kristans Slave, if you like that kind of servitude.

popeye

Yes, I'd love to be a cum eating sissy fag for you, your aunt, lady and friends hehe

Very HOT encounters you have had!

I too would have loved to have been the cleanup boy for your aunt and her friends.
Cuck who loves a creampie.

Please don't let this amazing story end

Wow, amazing stories! I only just discovered this thread today, and it's wonderful. You can be sure I'll be visiting again!

love the idea of a "sissy party"

Again thanks for the comments and following, hope you enjoy this next installment...

One day my Aunt said she was going to “expand my experiences again” and told me to come round to her house and meet her there; we would both be going into the city.

I arrived at the allotted time and she was dressed very sexy in a black thin pencil skirt, stiletto ankle boots and a sheer see thru top with a sheer see thru black and pink bra on which showed plenty of nipple. She wore a short black jacket which was open, so you were constantly getting glimpses of hard dark nipple poking thru.
She said she was going to give me an art class at the local museum, which was the last thing I expected but went along with the “game”.

When we arrived, it was your typical art museum, large paintings hanging on the walls with not many folks around with old guards watching you as you walked into the rooms to see the art. I complained that this was not my idea of an afternoon out, but she said to “be patient and to appreciate all that I could see”.

Then we entered a room where the guard was a young looking guy, who at first was sitting in a chair at the side of the gallery. As we walked in he watched us, and after a short while stood up and moved slowly towards us. He, I felt, was just checking out my Aunt, who removed her jacket as she noticed this young man watching her. He made his way slowly around so that he could see my Aunt closer and from the front; he was obviously checking out her tits. She whispered to me to “watch and listen”. She then walked straight up to the guard and asked him if he “knew anything about that painting on the wall”, pointing at a large oil painting.

He explained that he was sorry, but he did not, as he was only doing this job to make some cash during the summer and “wasn’t really an art expert at all”. All the time he was talking he was staring at my Aunts tits. She made some small talk about a fit you man doing a boring job, but he explained it did have its perks. She then quite bluntly asked him “if her tits were one of those perks? as he seemed to be enjoying them”. He was quite flustered but said “yes” he did like them and in fact he “couldn’t take his eyes off them”. My Aunt then started to stroke his cock through his pants and said “this seems to like them too doesn’t he?” The young man then started to feel my Aunts tits and asking who I was. She said I was just her nephew and she was “teaching me the art of sex”. She then, right in the middle of the gallery, sank to her knees and unzipped the guy’s pants fishing out a large purple tipped cock which she proceeded to suck.

She told me to “watch out for anyone coming into the gallery” and proceeded to suck him off! He seemed to be fucking her mouth in rhythmic jerks and It did not take long for the young guy to announce he was “coming” as he held her head and he filled her mouth with his cum, my Aunt gagging as he spurted. My Aunt asked me if “I had a handkerchief”, but all I had was a couple of tissues in my pocket which she took and wiped some dribbles of cum from her chin, then returned the wet tissues to me, and thanked the guy for his time. She asked him “what time he got off” and he said “5pm”. She said she would be “waiting outside at that time in a silver ford if he wanted to have some more”.

When we got back to the car she kissed me deep and asked what I thought of the day? I could taste the guys cum on her mouth, but it didn’t taste bad or anything, and I said it was hot and asked if she knew that guy? “No” she said…”never met him until today, I just wanted to show you how easy it is to get a guy hot and in the mood when I feel like it”…”well he certainly seems interested in some more” I said.

We went home and had some lunch, and then my Aunt had me fuck her in the back yard over a lawn chair as she told me how the day would proceed. At 4:15pm I drove her car, with her in the back seat, back to the city and we pulled up right outside the museum at 5pm; after a few minutes the young guy appeared and climbed into the back seat with my Aunt as I drove the car. My Aunt had changed into a mini skirt and stockings and proceeded to give me instructions to “drive her home”. I kept trying to drive and check out what was happening in the back seat, and I nearly drove off the road a few times I can tell you. She soon had his cock out again, and had him deep in her mouth as she teased him and fed his hands up her skirt.

Soon we arrived home, and she took him inside as I parked the car in her garage. When I got in the house, she and the guy were on the settee and Uncle Joe was there, as he had come home from work and was being told to “get upstairs and get dressed for our new guest”. She told the young guy to ignore Uncle Joe as he was her slave and would do whatever she told him to do. The young guy ended up with his cock deep in Aunt Ivy and was fucking her for all he was worth when Uncle Joe re-appeared dressed in pink dress, white ankle socks and high heels. He was then told by Aunt Ivy to “lick her shoes and make his way up to her cunt”. The fact that there was a young guy’s cock in that cunt just made it better I guess. The young guy was not at all sure about this, but my Aunt assured him it would be all Ok and asked me to confirm it, which I did. I was hard as a rock again watching all of this, and my Aunt asked me to come nearer so she could “feel me”. She soon had my cock out and fed it into her mouth as she was fucked on her back by the guard, and Uncle Joe licked her cunt and the guards’ balls in the process.

Soon the guard said he was coming and my Aunt told him to “fill her pussy up” which with several loud grunts he did. Once he pulled out my Uncle proceeded to clean her out, and I said I was about to come too having been fucking her mouth for while. She pulled my cock out and told me to cum over her face, which I did in huge spurts, and covered her face in white ropes of cum. “Get up here and clean me up” she said to Uncle Joe, which of course he did. Afterwards we all had a beer, except Uncle Joe, who was told to sit facing the wall in the corner.

My Aunt was a very special woman and she had great control over her husband, and any other male for that matter. She was bold, slutty, and unashamed of her power over men…she was great and still is much the same today even though she is older. I am so lucky to have her and her friends in my life.

Absolutely great, thank you for sharing !

Are you still in touch with your aunts and everyone?

Popeye:

I loved hearing about your upbringing! I hope you'll continue to shed more light on this unique lifestyle that runs in your family. Wish I would have know your aunt and been one of her boy-toys.

Once again..... Thank You for sharing your adventure!!
Cuck who loves a creampie.

Kristens slave...see the very last line of my last post, so yes I am still in touch.



Thanks

Great story. Thanks for sharing.