Straight Male / 55
Double Mastectomy
My sister who is 5 years younger than me, began to develop sexually at a very early age, around 11. This made her popular with the boys at school, and less popular with the girls.
She blossomed into a very voluptous young woman, and I would try to steal glances of her breasts and cleavage whenever she wore a swimsuit or on the rare occassion that I accidently caught her in a bra.
I remember the glorious days of when halter tops where in style, and I could catch a glimpse of her puffy nipples under the cloth, and even sometimes some bare side boob.
But being siblings we ran in different crowds, and we went our separate ways. She got married and moved to a different city, while I bounced from one failed relationship to another.
Then one evening she called me in complete distress. She had just received some terrible news that her body was being ravished by cancer, and she had to have both a hysterectomy and double mastectomy. To add insult to injury, her cruel husband told her that she was no longer a woman and left her.
Although we were not that close, I tried to console her as best as I could, given that both of our parents were deceased. As the months passed both waiting for the surgery, then recuperating from it, my sister and I became closer through our phone conversations.
Eventually it looked like things were turning for the better, and my sister began to get healthy again. We made plans to take a vacation together. We booked some flights and met up in Cape Cod, on the premise that the sea air would do her some good.
However we did not plan well and booked only one hotel room for the two of us. It was no big deal, as we had often roomed and bunked together when we were growing up.
We had an exciting first day of walking along the beach and catching up. We were closer than we had ever been growing up. To top off the day, we had a huge seafood dinner, which made us want to go bed early.
We dressed for bed very conservatively, me in a sweat suit and pants, and her in flannel pjs. We climbed into our seperate queen beds, and I nodded off to sleep quickly.
Around midnight I was awoken by my sister sobbing uncontrollably. I asked her what was wrong. She said she was remembering what her husband had said to her about not being a woman, and she was worried that no man would ever want her again.
I told her that this was nonsense. I tried to put a positive spin on it, and reminded her that she was scheduled for augmentation surgery. She could get any size breasts that she wanted, that would have men drooling over her and make women green with envy.
She chuckled at this image, which seemed to help her calm down. I cradled her in my arms and softly stroked her face and hair. Then we began to kiss. At first butterfly kisses, but this eventually lead to full-on french kissing, with our tongues exploring each other's mouths.
Then she pulled back. At first I thought that I crossed a line. But she unbutton her pj top and exposed her chest to me. She asked me if I thought that she was still a woman. I said "of course", but I didn't let on how flat I thought she was nor that she had absolutely no nipples.
With a finger I began to gently trace around an outline of a circle where I thought her new breasts would be, trying out different sizes. She giggled and said that it tickled.
Remembering our tickle fights when we were kids, I work my way down to her waist and began to stroke her sides with a feather touch. This made her skirm and grind her hips in response.
Then I got real daring and reach my hand down into the crotch of her pj bottoms. The whole area was musty and then I insert my index finger into her sopping wet pussy. She let out a quiet moan.
Then I reach into her deeper, first with one and then two fingers, and began to massage her spongy g-spot. She never really squirted, but her pussy juices just flowed out of her. I also began to rub her clitty with my thumb.
By now my sister was mumbling incoherently, bucking wildly, grinding her pussy into my hand, and began to spasm in an uncontrollable orgasm.
After she recovered a bit, I made my sister turn over and get on all fours. She probably thought that I was going to fuck her doggy-style, but I had other plans.
I inserted a couple of my fingers again into her pussy, which was so well-lubricated with her juices by now. Then I inserted a third finger and this gave me a really good position to massage her g-spot. I next took my 4 fingers and formed them into a wedge. With a little thrust I was able to insert this wedge into her c**t, but she let out a yelp.
Finally I removed my 4 fingers and hide my thumb in the centre of the wedge. With a little twisting and turning, I was able to work my whole hand into her pussy.
Now I was literally fist-fucking my sister. I pounded away at her pussy, and every time I rotated my fist in her c**t she had another orgasm.
That night it was all about pleasuring my sister and making her feel like a woman again. Of course she did show her appreciation later, but that is another story.
My sister who is 5 years younger than me, began to develop sexually at a very early age, around 11. This made her popular with the boys at school, and less popular with the girls.
She blossomed into a very voluptous young woman, and I would try to steal glances of her breasts and cleavage whenever she wore a swimsuit or on the rare occassion that I accidently caught her in a bra.
I remember the glorious days of when halter tops where in style, and I could catch a glimpse of her puffy nipples under the cloth, and even sometimes some bare side boob.
But being siblings we ran in different crowds, and we went our separate ways. She got married and moved to a different city, while I bounced from one failed relationship to another.
Then one evening she called me in complete distress. She had just received some terrible news that her body was being ravished by cancer, and she had to have both a hysterectomy and double mastectomy. To add insult to injury, her cruel husband told her that she was no longer a woman and left her.
Although we were not that close, I tried to console her as best as I could, given that both of our parents were deceased. As the months passed both waiting for the surgery, then recuperating from it, my sister and I became closer through our phone conversations.
Eventually it looked like things were turning for the better, and my sister began to get healthy again. We made plans to take a vacation together. We booked some flights and met up in Cape Cod, on the premise that the sea air would do her some good.
However we did not plan well and booked only one hotel room for the two of us. It was no big deal, as we had often roomed and bunked together when we were growing up.
We had an exciting first day of walking along the beach and catching up. We were closer than we had ever been growing up. To top off the day, we had a huge seafood dinner, which made us want to go bed early.
We dressed for bed very conservatively, me in a sweat suit and pants, and her in flannel pjs. We climbed into our seperate queen beds, and I nodded off to sleep quickly.
Around midnight I was awoken by my sister sobbing uncontrollably. I asked her what was wrong. She said she was remembering what her husband had said to her about not being a woman, and she was worried that no man would ever want her again.
I told her that this was nonsense. I tried to put a positive spin on it, and reminded her that she was scheduled for augmentation surgery. She could get any size breasts that she wanted, that would have men drooling over her and make women green with envy.
She chuckled at this image, which seemed to help her calm down. I cradled her in my arms and softly stroked her face and hair. Then we began to kiss. At first butterfly kisses, but this eventually lead to full-on french kissing, with our tongues exploring each other's mouths.
Then she pulled back. At first I thought that I crossed a line. But she unbutton her pj top and exposed her chest to me. She asked me if I thought that she was still a woman. I said "of course", but I didn't let on how flat I thought she was nor that she had absolutely no nipples.
With a finger I began to gently trace around an outline of a circle where I thought her new breasts would be, trying out different sizes. She giggled and said that it tickled.
Remembering our tickle fights when we were kids, I work my way down to her waist and began to stroke her sides with a feather touch. This made her skirm and grind her hips in response.
Then I got real daring and reach my hand down into the crotch of her pj bottoms. The whole area was musty and then I insert my index finger into her sopping wet pussy. She let out a quiet moan.
Then I reach into her deeper, first with one and then two fingers, and began to massage her spongy g-spot. She never really squirted, but her pussy juices just flowed out of her. I also began to rub her clitty with my thumb.
By now my sister was mumbling incoherently, bucking wildly, grinding her pussy into my hand, and began to spasm in an uncontrollable orgasm.
After she recovered a bit, I made my sister turn over and get on all fours. She probably thought that I was going to fuck her doggy-style, but I had other plans.
I inserted a couple of my fingers again into her pussy, which was so well-lubricated with her juices by now. Then I inserted a third finger and this gave me a really good position to massage her g-spot. I next took my 4 fingers and formed them into a wedge. With a little thrust I was able to insert this wedge into her c**t, but she let out a yelp.
Finally I removed my 4 fingers and hide my thumb in the centre of the wedge. With a little twisting and turning, I was able to work my whole hand into her pussy.
Now I was literally fist-fucking my sister. I pounded away at her pussy, and every time I rotated my fist in her c**t she had another orgasm.
That night it was all about pleasuring my sister and making her feel like a woman again. Of course she did show her appreciation later, but that is another story.
