These events took place just over twenty years ago, shortly after my eighteenth birthday, and describe my introduction to the delicious pleasures of cross-dressing. It was also when I learned that my parents and their extended family of siblings and cousins enjoyed a discreetly incestuous lifestyle into which we were initiated once we officially became adults.
These days I generally limit myself to wearing ladies sexy lingerie underneath my normal masculine attire, or in bed at night, although in special occasions my wife and I visit specialist clubs for swingers who enjoy the pleasures of gender role reversal and strap-on sex. Over the years I have built up a wardrobe of female apparel and a selection of wigs of different colours and styles, and fortunately, I have managed to maintain my slender figure so that with the right padding and well-applied makeup I can still turn a few heads. My wife is quite tall and slim with short dark hair, and she looks really hot in a sharp suit, especially as I know that she is packing one of her collection of strap-on cocks.
§§§§§
“Keithy is that you?
“Hi Aunt Emily, yes it’s me.
“Just go into my bedroom and put the package from your mum on the dressing table. I’ll be with you in a minute. You can lie down on the bed if you like, but please take your shoes off.”
“Okay, Aunty.”
A few minutes after this exchange my aunt came into the bedroom wearing a pale green silk wrap-around robe tied at the waist. It was obvious that she wasn’t wearing a bra and her full breasts and prominent nipples were barely contained by the diaphanous material, and my cock began to grow involuntarily at the sight and soon made an obvious bulge in my jeans.
“Mmmm Keithy, you do look pleased to see me, you naughty boy, which only goes to prove what your mother says must be true.”
“What is that Aunty?”
“Well, she tells me that you’ve been a very wicked young man and that you’ve been sneakily taking her knickers out of the dirty linen basket. I wonder — do you sniff them?”
I blushed to the roots of my hair.
“Aha, you don’t deny it then, which would be silly given that you’ve gone a rather delicious shade of pink.”
“No, I mean yes, Aunty.”
“And is that all, you kinky boy? Come on, tell the truth.”
“Er no, Aunty. I take my clothes off and put the knickers on — and mummy’s bra and stockings.”
“That’s not all though is it. Angie tells me you’ve been sneakily watching her undress when she has her morning shower. I wonder what you find most arousing — her boobs, or her bottom — or is it her pussy? I bet it makes you so horny that you go and wank in your bedroom thinking about touching her — or even fucking her.”
“Hmm yes, Aunty, but she’s very beautiful — just like you — and you are both so much sexier than the girls on the Internet. Watching her makes my cock so hard I have to wank.”
“Dear Keithy, that’s very normal, but you’re a young man and you cum so much that the mess in her knickers is hard to wash out. Angie and I have been talking about it and we thought you should have some sexy underwear of your own. That’s what’s in the package.”
“But why did Mum send me round to you?”
“Well, we both thought that to start off it would be better if I helped you. Later on, your mother will be very happy for you to sit in her bedroom wearing your lingerie while she undresses, and then she’ll let you play with her boobs and maybe even her pussy. But you won’t be allowed to fuck her just yet; that will come later.”
“Oo-er Aunty, won’t Dad be upset, and will I be allowed to wank while I’m watching her?”
“Keithy, my sweet boy, your Dad also likes to dress in women’s clothing — it’s called cross-dressing — and he and your mum often come round here for the evening along with our cousins and two or three of our special friends and we all spend the evening wearing just our sexy underwear — well, to start with anyway — we usually end up naked.”
“Er, Aunty, what happens then?
“Silly boy, we end up fucking each other; with several different partners usually, and not just the men with the women — the men need a rest after they cum, but we ladies don’t. Now that you have had your eighteenth birthday we think that the time is right for you and your cousin Lizzie to join us. However, you must be properly prepared so that you know exactly how to make sure that both you and the person you are fucking reach the highest level of sexual ecstasy every time. Until then, your mother and I will be teaching you everything you need to know, and your father and Uncle Peter will be doing the same for Lizzie.”
“That all sounds a bit awesome Aunty, so what exactly is going to happen?”
“Don’t worry, you will definitely enjoy it, but you won’t be allowed to fuck either of us until after your initiation, which I can assure you will be really memorable for both you and Lizzie. Beginning this morning, your mother and I will have regular sex sessions with you when you will be allowed to stroke your cock but not to cum. We will take care of your orgasms when we think you are ready, either using our hands or by giving you a blow job. You will also learn the absolutely essential skill of bringing a lady to orgasm after orgasm using your fingers, lips and tongue.”
By now my cock was so hard that I was beginning to feel very uncomfortable, so what my aunt said next was almost a relief, although it was still rather a shock.
“Now Keithy, take off all your clothes so that I can see your equipment. Your cock looks rather gorgeous if that bulge in your jeans is anything to go by.”
“Erm Aunty, are you sure, I mean you are…”
“Nonsense Keithy, I’ve been looking forward to this day for a long time.”
It didn’t take long for me to strip off my tee-shirt and jeans. I hesitated when it came to removing my briefs, but a sharp look and an impatient gesture by my aunt made it clear that by all my clothes she meant everything.
“Oh Keithy you look lovely naked, and your cock really is magnificent, even before it’s fully erect, and I love the way your balls hang down. I reckon you’re even bigger than your father and that upward curve of your cock is guaranteed to stimulate a lady’s g-spot. But we must get rid of all that hair, the sensations when you have sex will be so much more intense without it.”
Aunt Emily then led me out of the bedroom into the bathroom where she made me stand in the bath whilst she liberally soaped up my cock and balls and the region around my anus. About fifteen minutes later we were back in the bedroom where she made me stand with my legs apart in front of her so that she could spread lotion on my freshly shaved genitals.
The effect of her expert massage was to make my cock stand up more proudly than I could ever remember, and as she slowly stroked it from my balls all the way to the swollen and throbbing glans I could feel that exquisite churning in my loins that meant that my orgasm was very close.
“Oh Aunty, that feels so wonderful. Please don’t stop, I’m nearly cumming.”
“Oh, the impatience of youth. You will soon find out that keeping you on the edge of your climax until you literally beg to be allowed to cum leads to an orgasm of an intensity you couldn’t have imagined. You might even pass out for a few moments. Now undo that package and put on what you find there — there should be bra and panties, a suspender belt and stockings.”
I immediately did as I was told and for the first time in my life, I felt that melting feeling of erotic excitement that I later came to know so well whenever I was wearing ladies lingerie, and especially when I was being caressed by a beautiful woman.
“Oh you look so delicious I could eat you — which I will probably do later. Don’t you feel sexy? We must buy you some sexy dresses and high heeled shoes next week, and a nice long blonde wig. I didn’t tell you before, but we occasionally go to an adult sex club where everyone is dressed as the opposite sex. All the ladies will want to fuck you. Some ladies wear a strap-on cock so they can fuck those men who enjoy anal sex — it’s called pegging. Your father really loves it; he often cums two or three times in an evening. But you need to experiment in a safe environment first, with me or perhaps Lizzie.”
“Oh Aunty, you are so naughty, but in a nice way and it feels so right. I think I will enjoy you fucking me, I could cum just thinking about it.”
“You are so like your father! I have never felt him harder than when I’m penetrating him from behind, but it’s a special privilege when he’s been a really good boy and licked me to several orgasms. That’s a skill that I will enjoy teaching you, but not today. This afternoon I will let you see me naked and allow you to kiss my boobs and finger my pussy, I just have to undo this and open my robe.”
“Wow, oh gosh Aunty, your boobs are amazing and your nipples are so long, please can I suck them.”
“Of course my lover boy, just lie back on the bed so I can straddle your tummy and I will lean forwards and… oh! Oh yes, just like that. Oh, Keithy you are a natural and the way you nibble my nipples send shocks down into my pussy. Give me your hand and I will guide you just where I want you to put your fingers.”
“Oh Aunty, you are so wet and hot, and your cunt is soft like velvet. I want so much to put my cock in there, are you sure we can’t fuck this afternoon?”
“I want to feel your cock throbbing and pulsing as you fill my cunt with your hot cum just as much as you do but we must wait until after your initiation. Then you can fuck me as often as you want. Now let me slide back a little so I can feel the end of your cock in the crack of my arse. Now just curl your fingers up a little and stroke the walls of my cunt while I rub my clit, and keep in sucking my boob. I’m so hot it won’t be… long… oh, oh, oh, aaaaargh, I’m cumming. Oh my God, fuck, that is so strong… “
“Are you alright, Aunty? You went limp. I thought that you had fainted.”
“Oh my Keithy, that was wonderful, truly amazing. You are going to be a wonderful lover. Our evenings are going to be even more exciting, and with your stamina, I expect you will cum in all the ladies. I’m so jealous that Lizzie is going to be your first — oh dear, that has let the cat out of the bag. I will have to tell you all, but not until I have made you cum — I think in my mouth would be best. A little premature but I’m so horny I really must taste your cum.”
End of episode 1.
