Sister-in-law Prostate Massage Ch. 01

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I couldn’t believe it was about to come true. A fantasy/daydream that I have had for over 40 years was about to become reality. As she unbuttoned her blouse, my adrenalin began to flow as it did when I lost my virginity so many years past.

She was my wife’s older sister. I had known her longer than I have known my wife. We were classmates throughout high school. I had always had a crush on her, but I was too shy and backwards in high school to ask her out. Besides, she was BEAUTIFUL, why would she want to go out with the likes of me?

I had met her younger sister shortly after high school graduation. The two sisters were as different as night and day. Not in appearance, but rather in personalities.

To describe my sister-in-law, she resembles Lesley Ann Down in appearance, both in younger and present years. Her personality could best be described as the character Dawn Wells portrayed as Mary Ann on “Gilligan’s Island”. She is soft spoken and sweet and innocent.

To describe my wife, she resembles Laurie Metcalf in appearance. Her personality could be best described as the character Roseanne Barr portrayed as Roseanne Conner on “Rosanne”. She is loud and crude and not much of a lady. Full of insults and sarcasm.

For clarity, throughout this story, I will refer to my wife as Rosanne. I will refer to my sister-in-law as Lesley.

When I met Roseanne, I was very insecure about myself. I was also, young and dumb and full of cum. I really didn’t know what I really wanted in a wife. Roseanne reminded me of my Aunt, and I think that is why I was attracted to her. (Read my story “In Memory of Aunt Lisa”)

Roseanne is Tom-Boyish and rough, where Lesley is a Lady. Don’t get me wrong, my wife is attractive, but her sister is beautiful.

When Roseanne and I were dating, she gave the most fantastic head. (Which I had mistaken for love.) That ended after marriage. As the joke goes, “Why do brides smile so much?” “They know they have given their last blowjob.” Ever so true with my bride.

As I mentioned, I did not know what I wanted in a wife. I thought Roseanne was the type of woman that I wanted, but after a few years of the Roseanne Conner personality, I realized that wasn’t what I wanted in a wife. I wanted a Lady. I got tired of seeing her in sweat pants or pant suits. When we would get together at family gatherings during the holidays, she would be in baggy jeans or sweat pants and baggy flannel shirt. Lesley would show up in a dress with stockings and heels or a skirt and blouse.

Lesley would sit straight and proper, just the opposite of Roseanne’s slouching forward or leaning back with her legs wide spread. I was ashamed to admit that Roseanne was my wife. Soon I started fantasizing about Lesley when I was with Roseanne, both in public and in the bedroom. As previously mentioned, a fantasy that has been going on for over 40 years.

Lesley was married to a jealous, possessive man. His personality reminded me of that of Al Bundy from “Married With Children”. So therefore, I will refer to him as “Al” in this story. He did not allow her to visit her siblings that often, even though we only lived about 6 miles apart. Family holiday gatherings were about the only time I got to see her. (It wasn’t until years later and the invention of cell phones that Al permitted her to go places without him. But, she had to check in with him frequently via the cell phone.)

(Just a little aside to describe what a jerk he is: He would call Lesley on her cell phone. If she answered while driving the car, he would yell at her for doing that. If she wouldn’t answer while driving the car, he would continue to call her until she pulled over and answered the phone. Then he would yell at her for taking so long to answer his call.)

Lesley would telephone fake hospital hastane Roseanne a few times a week. I would always enjoy it when I was the one to answer the phone. I would usually spend a few minutes talking to her. Her soft, polite, lady like voice was so refreshing and also a turn on.

I recall one time she was telling me that Al had gotten into an argument with their neighbor. She quoted to me Al’s verbal statement to the neighbor. “Mother Fucker, if you don’t keep your dog out of my yard …” To hear her say “Mother Fucker” with her soft, sweet voice was in some way, erotic.

She would call and sometimes she would be talking to me and I could hear the sound of her peeing. (Thank goodness for portable phones) Apparently, she wouldn’t try to hide what she was doing, because I could hear the flush of the commode afterwards. To know that she was peeing while talking to me was a real rush. (Some may think it perverted, but sometimes I would fantasize that she would be giving me a golden shower.)

I recall the one time I almost saw her exposed breasts. Roseanne and I had gone on vacation for a week. We left our dog at Lesley’s house while we were gone. We returned home from vacation late at night, so the next morning I went to pick up the dog. I arrived around 9:00 am. Lesley answered the door dressed in a V- necked, knee length night shirt on. Al was still in bed, I guess. Lesley greeted me with a hug and I could feel her braless breasts underneath the shirt press against me. This created an instant stir in my jeans.

The dog was hiding behind the loveseat and wouldn’t come out. Lesley got down on her hands and knees to coax the dog out of hiding. (Seeing her in a doggie position was coaxing “my dog” to come out of hiding.)

I got down on my hands and knees too, and I positioned myself on the other side of the loveseat. I had a perfect down blouse view of her bare breasts. I couldn’t see the nipple area, but it sure was a good view. Her breasts were smaller than Roseanne’s, but that didn’t matter.

Finally, the dog came out my side of the love seat to me. When we stood back up, Lesley’s nipples were very hard and straining to poke holes through the material of her nightshirt. She came over to me and started fussing over the dog, which I was holding in my arms. As she stood close to me to pet the dog, I could feel her hardened nipple pressing against my forearm. I could feel precum starting to flow from my hardening manhood. I thanked her for watching the dog and headed out the door towards my car. She followed me outside, the coolness of the morning air made her nipples even harder. God, what a beautiful sight.

Years later, I developed some problems with my prostate. Not cancer, just an irritation called Prostatitis. It is usually cured with antibiotics, but it likes to hang on. My Urologist asked me how often do I ejaculate. My bedroom life has been stagnating for years, so if I ejaculated once a month, I was doing good, and that was usually while jerking off after reading Literotica stories, fantasizing about Lesley.

The Doctor said that I should ejaculate at least twice a week to keep a healthy prostate. He then suggested that I should get a prostate massage to push out backed up prostate fluids. He told me to bend over the table and then he inserted his lubed up, gloved finger and gently pushed on my prostate. The sensation felt like I was going to urinate, but he said to relax, it was prostate fluid coming out. He said I should feel relief from the Prostatitis from this, but suggested that I still get relief at least twice a week.

I went home and told Roseanne about this. She thought I was bullshitting her about the twice a week ejaculations. Then she alluded to the fact that perhaps my Urologist fake taxi porno was Gay and got his own ejaculations by shoving his finger up another man’s ass. She questioned my sexual preference, wanting to know if I enjoyed having a man’s finger up my ass. I knew that this conversation was leading nowhere, so I dropped the subject.

The next evening, Lesley telephoned. I spoke to her a few moments. Apparently, Roseanne told her that I had a doctor’s appointment because she asked me how things went. Embarrassed, not knowing what Roseanne had told her why I was going to the doctor’s, I just said everything was ok. I just have to accept some physical changes after a certain age. I handed the phone to Roseanne so that they could talk. I was rather irritated to overhear all the details of my prostate issues Roseanne was telling her sister.

I heard her sarcastically telling Lesley about the prostate massage and the ejaculations twice a week. I could hear Lesley’s muffled, inaudible voice as she was replying to Roseanne. Even the muffled sound of Lesley’s sweet voice was pleasurable to hear.

Then I heard Roseanne make the comment, “You’ve got to be shittin’ me? I’m not sticking my finger up his ass. He can stick his own finger up his ass!!!!!!”

Again, I could hear Lesley’s muffled, inaudible voice as she was replying to Roseanne.

“I bet he would enjoy that. OK, if you insist. Cya in a bit.”, Roseanne replied sarcastically.

Roseanne hung up the phone and told me to go get a shower, that Lesley was on her way over to show her how to massage my prostate.

I snickered at that remark and said, “yeah, right.”

Roseanne said, “No, seriously, she is coming over. She said that she massages Al’s prostate at least once a month. She has for years. Al told her that it will help prevent him from getting prostate cancer. I can’t believe that she believes that bullshit, but he has her convinced. So, she is coming over to show me how to do it, and you know her, once she gets something in her head, she’ll drive it in to the ground until she gets her way.”

So, as an obedient husband, I went and got a shower. I found it difficult to resist jerking off in the shower at the thought of Lesley giving me a prostate massage. Then I began to wonder if it was going to be a show and tell or just an explanation. I felt that there was no way that my fantasy of forty years was going to come true. I presumed that Lesley was just going to explain to Roseanne how to do it.

I finished my shower and put on my lounging pants and t-shirt and awaited Lesley’s arrival.

Lesley arrived a short time later. It was always refreshing to see her. She was always smiling and cheerful. She greeted me with a hug and a kiss, and joking said, “Your nurse is here.”

We made small talk for a little while. She told me about her massaging Al’s prostate to keep him healthy. She then asked Roseanne where did she want to do this. We decided to do it in the bedroom.

Lesley handed me a towel and stepped outside the bedroom and told me to get undressed, lie on my back on the bed and to cover up my privates with the towel.

I remember thinking, “Damn! It is going to be just an explanation to Roseanne. Lesley doesn’t want to see my nakedness.” When I was undressed, and positioned and covered up, I called her back in. Roseanne was with her. Lesley was explaining the male anatomy to her about the prostate and its location and what to feel for. Lesley then pulled from her purse a tube of KY Jelly and a latex glove.

Roseanne said, “Wait a minute!!” and disappeared out of the room. She came back with another towel and said, “Here, put this under you. I don’t what shit stains all over my bed sheets.” (A remark like that sure takes the sexual excitement out of family stroke porno a prostate massage.)

Lesley said to me, “Scoochie your bum on down to the edge of the bed. Bend your knees and rest your feet on the bed.” She also instructed me to place a pillow under my lower back to raise up my pelvis.

“Scoochie your bum on down…..” What a difference between Leslie and Roseanne. Rosanne would probably have said, “Slide you ass down to edge of the bed!”

(Perhaps Scoochie doesn’t mean the same in all areas of the globe. In my area, it is a playful way of saying “Scoot”, which means ‘to slide’.)

To my pleasurable surprise, Lesley started to put the glove on her own hand. She was explaining to Roseanne what she was going to do. She lubed up her finger and reached under the towel and inserted her finger into my anus. I was fighting the urge not to get an erection. Lesley found my prostate and began to gently massage and push on it.

She instructed Roseanne to lift the towel so that she could see what was going on. Lesley kept her gaze towards my face. I felt the prostate fluid begin to flow, and I told her so. She eased up on her pressure and gently just massaged my prostate.

She told Roseanne that she enjoys sucking Al while she does this, but she gets too excited while sucking and it becomes a blow job instead of a prostate massage. She went on to say that she wants his cum in her mouth so bad that she gets carried away and pushes too hard on his prostate and hurts him.

Even with her talking dirty like that, she still seemed so innocent and lady like. What a turn on it was.

‘How can I not get an erection with this vision in my mind?’, I thought. But Roseanne’s reply to that kept any erection away.

Her remark to that was, “Well, that won’t be a problem here. I won’t be sucking his cock.

Lesley questioned, “You mean you don’t give him head?”

“Hell no.”, Roseanne said, “I had enough of that shit when I was dating guys. I don’t NEED to do it now.”

Lesley looked up at me, and with her ungloved hand, patted me on the chest and said, “Poor man, no wonder you have prostate problems.”

She asked me how the massage was feeling. She wanted to know if she was irritating my prostate. I told her it was burning a little. She said that she had better finish then. So, she continued to massage my prostate and with her other hand she rubbed my cock gently. The towel was separating her hand from actually touching my cock. Soon a rush of prostate fluid flowed from my soft, almost approaching semi hard, cock. I could not believe I survived this without getting a raging hard on.

Lesley asked Roseanne to go get a hot wash cloth. When Roseanne left the room, Lesley reached underneath the towel with her ungloved hand. She took a sample of my prostate fluid on to her fingertip. She then put her finger on to her tongue and tasted my prostate fluid.

She put her finger in front of her lips to form the “SHHH” gesture and winked at me.

Roseanne returned with the hot washcloth. Lesley suggested that I lay it over my penis for a few minutes to help relax my urethra.

Lesley told Roseanne that she would have to wait until later in the week for her to try giving me another prostate massage. It would probably irritate me too much if she did it too soon.

Lesley removed her glove and patted me on the thigh. She winked at me and said, “Hope that helps.”

All I could do was smile and said, “Thanks, I’m sure it will.”

I got cleaned up and dressed and joined the women in the living room for a night cap. Lesley asked us to please not tell Al about her giving me the prostate massage. I wasn’t planning on it, but a person never knew what Roseanne would blurt out.

Lesley soon prepared to go home. On her way out the door she said, “Now I need a semen fix, looks like Al is in for a prostate massage tonight too.” With that she kissed me on the cheek and left.

Roseanne remarked after the door was shut, “What a slut. She always was.”

To Be Continued…

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