tagMatureJenny Wren Ch. 01

Jenny Wren Ch. 01


This story contains descriptions of an explicitly sexual nature. Any participants have at least achieved their 18th birthday and all sex described herein is with mutual consent.

The story line and characters are entirely fictional: any similarities are purely coincidental.

It contains elements of the following: inter-generational incest; transvestitism; vaginal, anal and oral sex with references to spanking, BDSM, group sex and male and female bisexuality.

If such material is illegal in your current location, please click away from this page without reading further.

If the nature of this story is offensive in any way to you, you may feel more comfortable with other stories available on this site.

OK, that's the warnings out of the way. I hope you enjoy reading this story as much I enjoyed the writing.


Chapter 1: Caught in the act.

I woke gently from a dreamless sleep and opened my eyes to the glare of an August sun trying to burn its way through the curtains. Pushing the light covers to one side, I groaned a little as I rolled my body to the edge of the bed and sat there for a moment rubbing my right knee. "It'll be raining before the day's out," I muttered to myself. My arthritic knee was as good as those weather people on the radio when it came to predicting the rain.

But my old body was full of aches this morning. It didn't help that it was the anniversary of my Petey's death. I decided to treat myself to a mustard bath to ease my joints. Pulling off my nightie I turned to reach for my bathrobe, catching a glimpse of myself in the dressing table mirror and for a fleeting moment it seemed that the years had stripped away and I had my young body back. I smiled at my overactive imagination and it was my old, wrinkled body which smiled back at me.

I sighed and tried to conjure back that vision of the nubile girl I used to be. Gone now was that young beauty, the face I saw was wrinkled and careworn. I smoothed my bony hands over my hips and thighs as I had done so many times over the years and even attempted a sexy wiggle of my hips but the old bones didn't wiggle; the shrivelled skin just wobbled a bit. The breasts which used to threaten to burst out of any blouse or sweater or DD bra I wore now hung down from my bony chest with the nipples, once so proud and erect, looking at the floor.

I smiled as I noticed the small gold rings through them, remembering the day my Petey held my hand as a strange man had pierced them with a fierce-looking needle and then inserted the bars. I was so proud of myself when I barely flinched. This was years before piercings became commonplace and my various nipple ornaments often brought gasps of surprise when revealed for the first time. As I stood there I twiddled the rings reminiscing about the things Petey, and others, had done to them over the years. It was those memories which kept the rings in place when only I ever saw them. I brushed a tear from my rheumy eye, pulled my bathrobe over my shoulders, wincing at the ache then grabbed my stick and hobbled towards the bathroom.

I wondered why the master bedroom door was open so I looked in and saw Clive, still in his pyjamas, going through his mother's dressing table drawers. He had a lacy red brassiere in one hand and was retrieving a matching pair of panties with the other.

"And what do you think you're doing, young man?" I said in my most imperious voice. As he turned towards me his face went white then suffused to a bright red.

"G-G-Gaygan," he stuttered, "I was ... er ... I er ..." He hung his head and looked so pathetic with those incriminating articles dangling from his hands and a tent very quickly deflating between his legs. I stood with my back to the door and stepped backwards until it clicked home. On hearing the door close he looked up in panic like an animal in a trap, the flimsy garments dropping from lifeless hands..

"Well, what are you doing – or what were you about to do?" He remained mute, almost defiant. "Were you going to wear them and then play with yourself?" The blush renewed itself but he remained silent. "Were you?" I snapped harshly.

"Gaygan, I ..."

"Answer me." I demanded. Still not speaking he hung his head again and barely nodded. "Well?"

A tortured voice half whispered, "Yes, Gaygan."

I moved over and sat on the bed. "Then do it, Clive. Here and now, put them on."

"What? No way," he blurted out then stared me in the eyes with mutiny in his. But I had stared down bigger men than him in my life. I had role-played the dominatrix so often it came naturally to me. We remained like that for several minutes, glaring at each other and, as I felt his nerve begin to sway, I allowed a smile to cross my lips. It felt good to be in control again. His eyes slid away from mine and with a defeated sigh started to unbutton his jacket

Clive was my great grandson, 19 and in the prime of his life. Gaygan was what he used to call me when he was just a toddler. He couldn't get his mouth around 'great grandmother' so I became Gaygan and so have been called by all the family ever since.

My heart skipped a beat when I saw him standing before me stripped. I hadn't really noticed it until now: he was a mirror image of my Petey when we were on our honeymoon. Standing at about 5'9", Clive displayed a finely honed body and the cutest bum. His light brown hair fell neatly about his ears and his eyes were deep liquid brown pools framed by sensually long dark lashes. His quiescent manhood twitched as my gaze settled on it. The soft cylinder came to a point where the prepuce closed over the glans penis. It looked unnervingly familiar; half-hiding behind the luxuriant bush of pubic hair, it masked one testicle but revealed the other hanging heavily in the loose, wrinkled sac. Everything so achingly reminiscent of Petey; I was certain that body held no secrets.

My beloved late husband had a massive heart attack 20 years ago – so young, oh so young. It was a few months after he died that my granddaughter Mary, pregnant with Clive, and her husband Jack moved in to my house. They had lost theirs in a business deal which had gone sour through factors totally out of their control and I had a big rambling house which echoed around me. They were currently away on a business stroke holiday trip in Cornwall for the week.

At first I had only intended having a harmless tease with Clive but seeing him like that ignited a once familiar tingle in my clitoris and I found myself with my hand inside my bathrobe fingering my nipple ring.

Now I knew I had him under my control I could relax my psychological grip so I started to reassure him. "Clive, lots of men like ladies' underwear. Your great grandfather often used to wear a pair of my knickers under his trousers. It doesn't mean you're any less the man. Come, give your old Gaygan a kiss then dress up prettily for her."

I pulled my breast into the open as he stepped over and made to kiss my cheek but I turned my head and caught him full on the lips. It was a chaste, closed mouth kiss at first but he held it for a few seconds before finally responded to my probing tongue. Then Clive put one hand at the back of my head, the other over my hand on my tit, twisted the ring and gave me a real toe-curling kiss. Whoosh, it was like a heavy drink. As he stepped back I noticed he was semi-erect, and it had all the signs of being a lovely erection. Again, so much like Petey it was untrue. I kissed the tip of my finger, touched it to the top of his growing penis and said, "Hello, big boy. Are you pleased to see me?" It twitched.

He became more playful as he strapped on the bra. He was very dainty as he stepped into the panties and pulled them up over his now full erection, leaving the tip sticking out above the top.

"Get some of your mother's stockings out and bring them to me," I ordered. I stuffed the B cups with the nylons, squeezed his new tit then turned him round and let him see himself in the mirror. "See, I knew you'd make a pretty girl. But we need to do something with this." I reached round and flicked the top of his penis.

"Come here," I ordered, pulling him round to face me again. I held my breast to him and said, "You play with this while Gaygan gets rid of that silly interruption. He took my flabby old tit but was fascinated by the ring, lifting, tugging and twisting it deliciously.

I pulled his panties down and slid a hot prick in my mouth for the first time in too long. It felt and tasted lovely but now wasn't the time to make love to his penis; I just wanted to get rid of the urgency. He was obviously enjoying himself tripping the light fantastic with my nipple ring so, without any hesitation, I took the erection all the way into my throat although I had to suppress the gagging reflex – it had been so long. Squeezing my throat muscles I milked him and it was only a few seconds until I felt the first pulse travel up his prick and his grip on my tit tightened to the point of delicious pain. I pulled back a little until it was shooting in my mouth: I hungered for the taste again. I cleaned him off then offered up my face for him to kiss me. I think he was a little startled to taste himself in my mouth but he barely hesitated before kissing me right back.

I tucked his softening penis back into the panties and pulled them up again. "Now get one of your mother's pretty dresses and put it on." He turned and opened her wardrobe and took his time picking a red print floral slim-fitting summer dress, held it next to his body and turned with one eyebrow cocked in query. I smiled and nodded so he closed the wardrobe and slipped the dress over his head then turned and showed me.

I clapped my hands in approval and smiled. "Now get yourself some shoes to wear." He found some red slingbacks with a 3" heel and I thought, "He's a bit ambitious." I had to help him loosen the back buckle as his mother's feet were smaller than his but he managed to squeeze into them.

"Oh, you are a pretty girl." I said as he stepped back again. I motioned with my finger, "Twirl round." He obliged then tried to drop a little curtsy, tripped himself up and fell giggling to the floor. "You'll learn!" I told him.

Chapter 2: The Bet

When he recovered himself I told him, "Go and run a nice hot bath for Gaygan, then come back here while the water's running." He tried his best but he just wasn't used to walking in heels and stumbled a little but made it to the bathroom and back safely.

"Come here; sit by me while it's filling." He did as I asked. "I like having my tits played with. My cunt and arse like attention too." I deliberately used the crude words so he would know I wouldn't be shocked. He lowered me until my back was on the bed, opened my gown wide and started playing his hands over my old flesh reviving delicious memories. I closed my eyes and it was incredible.

I was transported back 45 years to a caravan and hiking holiday in Devon. Petey and I had found a tiny remote cove which couldn't be overlooked except from the top of the cliff on the other side of the cove. He spread me out naked on a towel in the sun and ran his hands all over me in smooth stroking rhythms. It felt so loving and erotic especially when he told me there were two men watching from the path and both had binoculars directed towards us. I had an orgasm there and then. Another mind blaster hit me when he ostentatiously played with my body jewellery. And a third as he entered and fucked me after twenty minutes of that heavenly manipulation. I remember blowing a kiss at the two guys on the cliff after the performance ended. They both gave us a standing ovation, clapping their hands above their heads. One of them pointed to his groin and mimed masturbating. I signalled back the 'thumbs up'.

Clive's hands felt just like Petey's as they stroked over me. He stopped briefly when he discovered the tiny bar through my clitoris then started to explore the new-found jewellery. I was now so grateful I had never let my piercings heal over. He started one hand playing with my nipples, going from one side to the other. His other hand was twisting and pulling on my clitoris bar alternating with a thumb stabbing into my pussy. "Oh Petey ..." I screamed in orgasm.

"Are you OK Gaygan?" Clive sounded worried. My panting breathing wasn't reassuring him either.

"Phew," I gasped. "That was a good one. Thank you so much Clive. My husband used to do that to me and you did it so well. You're lovely." I pulled him down to me and kissed him thoroughly.

"That was really impressive, Gaygan. You had me scared for a minute. My girlfriend has never gone off like that."

"Thank you, kind sir or is it ..." I squeezed his tit and chuckled, "... kind miss? Help Gaygan to her bath now: would you like to scrub her back?"

He was surprised when he saw me adding some mustard to the water but this was a trick I learned from my grandmother. "It stimulates the blood circulation," I explained. "Warms aching joints." I lowered myself slowly into the hot water then sank right under for a couple of seconds before coming back up. Heavenly! I sat there soaking in the heat – physical and chemical – as Clive busied himself with my tit. I noticed he squirmed a little in discomfort in the tight clothing and shoes. "Why don't you get in with me? You can dress up again afterwards if you want. We'll fix you some makeup; would you like that?" He quickly stripped off his new clothes and sank himself gingerly into the other end of the big tub.

I massaged his tool with my foot as he became accustomed to the temperature and smiled as I felt it rise at my bidding. "Tell me, Clive, what do you see in this old body that causes this?" I dug my toes into his erection which was trying to peep out the water. "Look, it's like a periscope coming up to look at me." I joked.

He knelt up and started washing me. "I don't know what it is, Gaygan. My girlfriend has a gorgeous body and we have great sex together but I have never met anyone who is as sexy as you. Somehow you ooze sex. Your eyes see into me," he leaned over and ran a thumb across my lips. "Your lips ooze sex; your kisses just blow my mind. Your tits ..." his fingers biting into the flesh, "... ooze sex; yes even these flabby things. Your rings ooze sex. Your pussy, your cunt, your bejewelled clitoris oozes sex." His fingers invaded me. I certainly was oozing sex down there. "That's what causes this." He placed .my hand on his prick which I squeezed.

"Listen Clive," I said to break the silence as I sat there enjoying him enjoying my body. "We're on our own for a week. Would you like to spend that week making love to an old hag? I promise you this sexy old hag will be exciting. You can dress up as much as you like. I'll help you. I might dress you as my maid and you can wait on me hand and foot. We can do whatever WE want. Clive, my darling, how would you like me to spank you? Or you can spank me? Hush, lover," I put a finger to his lips as I saw the protest rising. "You've never tried it. We'll never do anything you don't want. I'll never ask you to do more than I reckon you can. You can call quits at any time.

"Listen, I've had a lovely sex life and had so many men, and women, with my husband's blessing: he would often be one of several giving me a good old fashioned gangbang fucking. With an open mind, I've learned so many erotic and sexy things. My husband and I had a motto. We'd try anything once: twice if we liked it. Ruling nothing out!

"If you are happy to service an old hag for a week, this old hag will take you on a trip to the moon, stopping at all points on the way."

Without saying a word he stood up, stepped out of the bath and helped me out. He got a towel from the airing cupboard and ever so gently he patted me dry, dusting me down with talc when I indicated. He quickly towelled himself dry, grabbed my stick, picked me up and bodily carried me to my bed. He placed my stick by the side table then mounted the bed and, spreading my thighs, knelt between them, leant forward and kissed me.

"Gaygan," he said, looking into my eyes, "Can you manage this? I'm 19 and you're ... just how old are you Gaygan?"

"I'm 77 years old and I'll make a bet with you." I kissed him back. "My body is yours for the day. No holds barred, whatever, whenever and wherever you want. If I cry quits before midnight tonight for any reason, you can fuck me twice a day for the rest of the week. If I win you'll be under my instruction for the week. Same conditions, you can say 'No' to anything."

But right now, do me a favour. Fuck this old witch silly. You've got her cauldron bubbling." I grabbed his face and kissed him. Keeping most of his weight on his arms he entered me slowly but all the way. I felt every lovely inch of it, every pulsing vein and every bump. He held stock still when he had full penetration then started rocking back and forth, allowing me to savour the actions Ever so slowly, as if tuning me, he increased his rhythm. An errant thought crossed my mind: "He will make a good pupil." His speed gathered until he was humping me and I was mewling in his ear.

Clive pushed all the way in then pulled all the way out again until the head was just hovering at my entrance then he jerked a couple of inches forward, just enough to get the swollen head inside then pulled it straight back out, repeating this in-and-out jerk every couple of seconds. "Oh no, not that ..." The only man who ever done this to me had been my husband. I just came and came and came, calling Petey's name as he kept the rhythm up before sinking deep into me and spurting his load in my depths.

"I hope I don't need a condom." His giggle cut through the mists of orgasm. "Are you on the pill Gaygan?"

"Silly boy," I said, slapping his rump playfully. "My eggs gave out over thirty years ago"

"In that case, Gaygan, light that touch paper and take me to the moon. The bet's on! And Gaygan, if you slip and call me Petey again, I won't mind." He smiled and it was like Petey looking back at me.

I thanked him then smiled to myself. Not ten years ago I had kept five men and two women happy for 24 hours. Even now I reckoned I could take on three prime stallions: just one would be easy. This week would probably be my sexually active swansong – comeback performance, as it were, but by god, I reckoned I could sign out with a bang.

Chapter 3: The Training Begins.

"Right, Clive, it's your day, your call. What do we do now?"

He smiled sheepishly, "I'd like to dress up again. Will you do my makeup, as you said you would?"

"Of course I will. Go and get your clothes and bring them here. You might also bring my robe; I can't sit around naked all day."

He scrambled off the bed to do my bidding and, as he turned away I slapped his rump again. "Ouch, what was that for?" He twisted round to see the red handprint I had left.

"That was just a warning: you never kissed me! Lesson: always and everywhere, kiss. A kiss says everything: that you're enjoying yourself, that you love what we're doing together, that you love me."

"Of course I love you Gaygan." He threw his arms around me and kissed me thoroughly before setting off for the bathroom almost at a run. While he was doing that I opened the curtains to let the sun stream in, noticing that there was a layer of cloud darkening over the far hills. My old knee had got it right again.

He returned with a bundle of clothes in his arms and placed them on the bed. He helped me in to my bathrobe then stood in front of me when I told him to. I walked around him, trailing a nail over his pectorals and digging in a little as it crossed his nipples, over his shoulder and down his back to his buttocks, noticing the fine trim. I trailed my nail round the front and across his penis which was already showing the beginnings of life again. I fondled then squeezed his genitals enough to make him gasp.

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