Summer House

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A mature's sissy fantasy is satisfied.
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KathyXX
KathyXX
150 Followers

I moved into the house at the beach after the divorce, my wife kept every thing else which was fine with me, there were no hard feelings I knew it was time.

This was the first summer I'd rent out the apartment in back, it was a one room kitchenet and bath with a small shower. With the beaches and board walk there were always jobs, mostly filled by 18yo teens working their summer break before college. It was easy to rent.

I'd take my time looking for that special tenant, the slim young closet fem that was keeping his secret from family and friends, just like I did at his age. That's how I met Ken, or Kathy the name she liked being called.

He was the son of one of the ex's friends and she'd asked me about renting him the place, she said he was, nice quite and spent must of his time studying. He'd be perfect, you wouldn't no he was there. She knew I like my privacy but never really knew why.

When I met Ken he wasn't what I expected, it was a really pleasant surprise. He was about 5'5 and 140, curly brown hair just below his ears, smooth skin barley shaven, so fem an sexy I was afraid my bulge would start to show.

At first he seemed nervous, almost shy but as I talked about him staying here and how I thought it would be nice to have him around he began to relax.

I told Ken the room was his and he could spend the summer and move in next week after graduation, both my ex and his parents felt better knowing

he'd be with me. With them paying he could just enjoy his summer break.

That first week as we got to know each other I could see Ken becoming more relaxed and comfortable around the house and with me. There wasn't much nightlife other then the beach or boardwalk it was home nights watching tv or playing games.

The more time we spent alone I noticed the fem side of her slowly emerging even though he tried to keep it hidden.

After dinner as we watched tv I always opened wine to relax the both of us watching Ken come out a little more each night.

During the morning I'd lay out in the small privacy fenced yard for a little sun and Ken began doing the same. At first he seemed nervous but it soon passed after awhile.

We'd been laying out for almost an hour and I couldn't take my eyes off him. That slim smooth body, a tight nylon bikini brief showing the perfect outline of a small soft clit. I couldn't wait any longer it was time.

''Here sit up for a minute, you need a little screen,'' with his back to me I slowly began rubbing on the lotion, '' That's it.''

As I slowly and softly began running my hands over his back it was obvious how much he was enjoying it, almost as much as I was. ''Why don't you lay on your stomach,'' he did, ''close your eyes and just relax.''

With the lotion my hands slid gently over his shoulders an arms, across his back and soft 18yo body. Ken just laid there not saying a word as the nervousness faded and he began to enjoy being touched.

I ran my hands down his back and a long the bikini briefs nice and slow, my thumb just under the waist band I could feel him tense for a second and relax.

''Your so tense, I can feel it in your body let me see if I can help you,'' sliding onto his chair, ''that's better already''.

Sitting by his knees looking at Ken laying there so girl like, the curly brown hair softening his face, narrow shoulders an slim waist the smooth shapely legs. But it was his bubble butt that tingled my bulge.

The way the bikinis framed his ass left nothing to my imagination, the silky material tight over those soft round cheeks as it narrowed running between his legs. It was all I could do not to reach out and fondle them.

I squeezed some lotion on his calves and gently began working up his smooth legs and thighs, lightly using only my fingers and nails. As I moved higher up Kens inner thighs his legs slightly parted letting me as far up as I could without touching him.

Slowly teasing him, my hands running and up over his slightly exposed cheeks, again my thumbs just under the elastic bands. For the next few minutes each time my hands ran over Ken I fondled his sweet ass a little more. He just laid the without saying a word.

''That's it for your back, you can roll over again,'' as he did the bulge in his briefs showed he'd gotten aroused. I laid back on my lounge with a slight bulge showing through my own shorts, that would be enough for now.

After several minutes I told him, ''It's time for me to go inside and cool down it's getting really hot out here,'' standing up for another look, ''don't lay out to long.''

I stood inside watching as he laid there in the sun, my mind full of images and fantasy's as I slowly edged my growing cock. I couldn't help wondering what he was thinking about after my little rub down.

That night I got my answer when Ken came in to watch tv.

When came into the den, that special tingle ran through me and I could feel myself becoming heavy and hanging in my sweats. He was wearing a pair of old cutoffs, that were obviously to small by how they held his cheeks nice an tight. A light blue midriff tee, with the white knee high socks and sneakers, he looked so feminine all I could do was stare.

Ken had finely come out to me after the lotion this afternoon he realized my attraction to him wasn't just casual friends. Now here alone in the house with me he could finely be that little sissy Kathy he's always wanted to be and only I would know.

She stood there and slowly turned showing herself off before walking over in a sexy way with movement's so feminine and natural she'd actual become Kathy.

''Look at you, so hot an sexy, such a pretty little girl,'' she smiled almost blushing, ''Come over and sit here by me,'' lightly patting the sofa. ''You don't have to be nervous anymore.''

''I'm glade you like it, I wasn't sure if I should but I couldn't help myself,'' facing me, ''I hoped you would,'' she put her hand on my thigh.

Here I was, it was hard to believe this was happening to me after years of being a mature closet husband I was with the 18yo sissy of my dreams, a fantasy couldn't be more perfect. Or wiling to please.

Right off I could see how horny Ken was, his sexual frustrations growing for a while now, never being able to satisfy them except when alone locked in his room. But now the fear of being discovered was gone and he could finely have the satisfaction he desperately needed.

I moved closer putting my arm gently around him, ''You know how horny your making me,'' I leaned forward and kissed his open mouth.

That was all it took and Kathy came out, as we made out I felt Ken slip his hand up my thigh and gentle start fondling my heavy cock as he kissed me harder. I was the only mature he'd been with so I can imagine how my seven growing inches felt in his hand, I was his first daddy cock.

''You like that baby, yea you do don't you,'' the look on his face said everything, ''here is this what you want.'' I slipped off my sweats and sat back naked on the sofa, ''There is this better.''

He gave me a sly grin and lowered his head, my cock jumped at the feel of his tongue as he slowly and teasingly began licking my hardening cock. I could see how much she was enjoying me so I leaned back and watched.

She was beyond words the way she treated cock, slow enjoying every inch, the way she softly nibbled my tight sack, it was pure ecstasy like I'd never felt. I was hoping it was the same for Kathy.

Sitting Kathy up I kissed him hard on the mouth, the taste of my own cock on his lips excited me even more, ''Come on,'' when we stood the wine showed, ''Here let me,'' putting my arm around her waist we went to the bedroom.

Earlier that day I'd spent time arranging it, dim lighting with a reddish tint, a tri fold mirror for every view, the bed stripped to a single white satin sheet. The tv set for porn vids and the nightstand vodka, poppers and a small camera clock.

Kenny looked around the room and went right to the mirror and stood there gazing at himself from every angle as I stood there behind him smiling back in the mirror.

''You look so sexy,'' kissing her neck, '' you should have something sexy to wear,'' taking him behind the mirror to a small dresser, ''my ex left this.'' The dresser was full of lingerie of all kinds, bras, panties, stockings, garters, a corset, everything for the perfect sissy boy. There was even makeup and a wig or two, none of it my ex's.

Reaching around Kathy I softly brushed his soft clit and put a popper on the dresser, whispering, ''Take your time, you sexy little girl,'' pressing against him, ''I'm going to freshen up.''

I went to the night stand and took my blue friend before relaxing with a warm shower and shave, wrapping in a robe I waited for her to call me back to my playroom.

While I sat on the sofa picturing Ken going through the lingerie, trying it on in front of the mirror, looking for that special outfit for daddies little sissy girl.

It's something we both needed, our secret urges and lustful taboo desires would be satisfied. I would have the 18yo slim fem in sexy boy in lingerie, and Kenny could finely the slutty sissy he's always dreamed of being.

Sitting there lost in fantasy, my cock becoming heavy and full as it hung between my legs the sound of the bedroom door had me turn my head in surprise. A rush of arousal and sexual lust as an electric tingle ran through my cock and balls.

Kathy was leaning against the door smiling as she blew me a kiss and turned back towards the bedroom. Kenny was in a lacy white matching bra and panties, with the shoulder length brown wig and makeup he was every fantasy I wanted.

Kathy was leaning against the bed as I locked the door behind me, she had a coy smile as she turned on the porn videos and inhaled a popper. I watched as she drifted into the euphoric sexual rush an hunger for the pleasures of raw lust filled sex.

Taking of the robe I stood by the mirror fondling my snake like cock as she sexually gilded over and stood inches from me. Looking at me Kenny took several long draws on the popper and handed it to me before going to his knees.

Watching him sucking my cock, dressed in his sexy lingerie took me into my own little world as I inhaled, the rush of the popper heightened my sexual pleasure.

When Kathy took me into her mouth it felt so warm an moist, a spasm ran through my body, she had to feel my cock throb as it slipped inside and began to grow. I stood watching the mirror as my eager sissy boy lost himself in the popper haze of lust and sexual satisfaction that only she could new.

Kenny had never let himself go like this before, his secret out this was the first time he could really become Kathy without the fear, his inhibitions gone the slut in him came out.

Watching her I could only imagine what was going through her mind remembering the first time I was free to satisfy my secret sexual urges without worry.

''That's it baby yea, go ahead you know you want it,'' rubbing my cock over his lips, ''show me you want a hard cock like a good sissy girl.'' As he worked my cock I kept us both in a popper fantasy.

For the next several hours Kenny was the sissy boy I'd wanted for so long, a sexy, feminine, 18yo horny little sissy slut. He couldn't get enough cock and with a blue pill I had a full hard seven inches for him.

We sucked and fucked until we were both spent in everyway we'd wanted to be, as we laid there I looked at Kenny as he drifted off to sleep knowing he was finely satisfied.

KathyXX
KathyXX
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MichaelfantasiesMichaelfantasies11 months ago

I love being touched! A man touching me, like in this story with the sunscreen... But then he stopped and left me laying there ! ? I put myself in character. Being alone and lonely, a man touching me like that would make me want more with him. Ken-Kathy, a young, femimine sissy boy was so lucky to find a loving man like in this story. I wished I was more open about my sexuality, years ago. Maybe I would have found an understanding man, like in this story.

AnonymousAnonymousover 2 years ago

The foundation of the story seems fine but the poor spelling and grammar are too distracting to make it enjoyable. Sorry.

AnonymousAnonymousover 2 years ago

It took two reviews to highlight the most glaring of items in your story.

Another, rather personal pet peeve, is the use of laid when lay is so much more appropriate; we laid vs we lay and he laid vs lay, when the subjects are already in supine positions.

These aside, what a fantastic story. I may have missed it but, is the main character able to be beachside continuously? We know (another grammatical slip) that the younger is available until college goes in for the fall semester.

Can only go four - 4 - but really like the setting and situitions set out in the established setting.

AnonymousAnonymousover 2 years ago

Check the sprlling and grammar before publishing your stuff, please. This could be a great story by using a proofreader.

AnonymousAnonymousover 2 years ago

Very much enjoyed, but the constant switching of pronouns is very distracting

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