I love my family. I have three sisters and a brother who are all older than me. My parents spaced us all about three years apart. As we grew up and matured, I was curious as our bodies changed and developed, which ended up feeding my hunger for sex. When I found my father’s cache of magazines from the fifties and sixties, I learned a lot about sex but the only live women I had as examples were my lovely sisters and mother.
Eventually, one of my sisters, Deb, became the focus of my desire as she loved to tease. To set this up a bit, Debbie is the middle sister and is 5’7” 110 lbs of slender gorgeousness, with shoulder length brown hair, brown eyes and 34b breasts. I am the youngest and 6’4” 160 pounds and almost eight inches– when hard.
She flashed me whenever we were alone, and a few times when we weren’t, but when only I could see. One of the best times was the first time I saw her pussy. She had dressed before I came into the room and, after I sat in front of her, turned facing me while she put on her sheer pantyhose over equally sheer small panties, raising her skirt to her waist in the process, and fully exposing her trimmed but hairy brunette mound. My mouth dropped as I saw the view, causing her to laugh and turn around exposing her ass to me as well. This view became part of my masturbatory fantasies for some time!
Throughout this time, I used to massage the tight necks and backs of my sisters after they came home from waitressing. Most of the time, my sisters would be in blouses and pants, but occasionally, I would sit astraddle their naked legs while rubbing and squeezing their necks, shoulders, and backs. I looked forward to these sessions with excitement and began to get erections on the rare occasion when I would be in shorts and they were too. The warm silky feeling of their skin on my skin as I sat on their thighs to rub them was amazing and exciting.
The best session began quite innocently. It was during the summer between college semesters and I was visiting my sister Debbie in her apartment. It was a hot day and shorts and t-shirts were the dress of the day. She was wearing a skin tight white t-shirt with no bra and her nipples were erect and visible, along with loose fitting red silky short shorts. To relax further, we had a beer and shared a joint and got little high, laughing about some of the stories from her job and from my school.
Deb was my closest confidante. We often spoke of our dating, and with the backdrop of the sex crazed seventies, we often spoke of the sex we were (or in my case weren’t) having.
“How is Breen (my latest girlfriend)?”
“Great," I answered.
“Have you made love yet?” she continued. I blushed
“No. I get very excited but well, I guess I am not in love with her.”
“Why do you say that? Is something wrong?”
I looked at the floor and mumbled out, “Yes, once I get to moving inside of her, I go soft. I am getting a little crazy about it as it is frustrating both of us, but her even more than me. At least I like licking her and making her orgasm that way but I want her to take my virginity.”
“You’re still a virgin?” Deb said, “Well no wonder. That can be a difficult time. I know it took me time to trust someone enough that sex was easy and wonderful. I’m sorry you are having a problem. It will resolve itself over time. You just need to keep trying and try to be in the moment versus in your head worrying. Want some more beer?”
Refreshed with beer, we shared another joint and got really stoned. It had been a long day of waiting tables for my sister at lunch and she was complaining of being sore in her shoulders and legs. We had taken our shoes off and I was rubbing her feet when Debbie turned to me and said with a glint in her eye “Hey, how about giving me one of your great massages? I could sure use one!”
With some excitement in my voice, in anticipation of what could happen, I viewed it as an invitation to more. I said, "Sure.”
We went to her bedroom and she lay on her bed face down, with her head facing left, resting on her folded arms. I started to straddle her legs, but my pants were pulling against my balls, so I stopped and took them off leaving me in my underwear. As I took my place straddled over her legs, the heat of her body was causing my heart to pound and my cock to rise halfway.
I reached across her back to begin the rub at her neck, making sure I didn’t press my half hard cock against her to ensure she would allow me to continue.
As I rubbed, she began to sigh, "That feels so good…”
I moved my hands from thumbing her neck to kneading her shoulders and she shifted so her arms were to her sides. My hands moved firmly down further over her mid back and into the middle, and then rubbing out over her ribs in the back.
“A little to the sides and up,” she said.
I moved my hand down on her sides and, as I slid up, I began to feel the bulge of her clothed breasts.
”Oh yes, that’s it," she said.
She immediately changed position raising her chest off the bed as she went on her elbows causing my hands to slide over her breasts and hard nipples which felt about an inch long. My hands Iingered on her soft breasts squeezing and pinching her nipples while my cock rose and was a rock. I had to adjust myself, taking a hand off her back. She lowered herself back to lying on the bed while I went further down her back to the top of her ass.
“That’s incredible! Keep doing that,” she said softly, as she raised her ass so that my clothed hard-on was lying on her crack.
Then, still up on her elbows, she said, "I’m getting very hot. Could you take my t-shirt off?”
Could I? I reached the bottom and pulled up,stripping off the white shirt and she went back to lying down. I continued to rub starting at her neck and shoulders, down her back and further to the small of her back. Then I moved down a bit so I had a better angle and my barely contained hard cock brushed between her somewhat open, very warm thighs.
As my hands reached her lower back at the top of her panties she raised her hips and said, "Please get my panties out of the way. You can take them off.”
Who was I to protest?
In a very trancelike, highly sexual state, I grasped the top of her silk panties and slowly pulled them down unveiling her beautiful ass and, as I pulled them over her thighs and down her legs, the very bottom of her apparently shaven pussy as not a hair was visible. Once the panties cleared her feet, as I turned to put them down, Deb shifted - lowered her midsection back to the bed, while she slightly opened her legs.
She turned her head to the side and with a big smile, said ,“Are you sure you’re comfortable? You seem constrained.”
To which I stuttered, "I-I- I’m ok.” I had to shift a bit to move my cock into a better position.
I was conflicted. Excited, but not knowing whether to press forward and try to make love to my sister or not. A fleeting thought of the fear of softness.
“But she seems to want it," my internal dialogue began. "Yes, but you don’t want to lose her love and respect afterwards. But she seems into it and is very hot…”
My little head won out and I said, ”Maybe you’re right. I am a bit uncomfortable."
So I got off the bed and stood up to peel my underwear off and my hard cock was erect in front of me. Deb had turned to look at me and my cock and smiled, putting her head back down on her folded arms. I smiled back and got back into the straddle position, my nakedness straddling her legs and my hard cock resting on her ass crack. I went back to beginning my massage at her shoulders and rubbing, kneading hard fingers exploring hot flesh, down over her shoulder blades as she wiggled her ass slightly, acknowledging the placement of my cock and sliding it deeper in her crack.
I sat back with my ass sitting on her legs withdrawing my cock back to a slight touch of my stretched foreskin on her skin. My hands proceeded down her back and over the cheeks of her ass. I began to knead her ass causing her crack to open slightly exposing the outer portion of her anus and the bottom of her pussy. My cock slowly moved forward, smearing precum on the skin between her anus and pussy.
She moaned and again raised her ass up as I moved my hands down to her upper thighs and my thumbs brushed some wetness – her pussy! Warm, wet and drolly. I went for broke and cupped her pussy,rubbing forward with one hand while my other went deeply between her cheeks and rubbed her anus. My cock went hard against the skin between.
She moaned and said, “Oh, Bill. Yes, keep doing that. Yes, rub me." She went up on all fours opening her ass, widening her legs and exposing herself totally to me.
I rubbed her hot wet pussy as I bent forward and began to kiss and lick her ass. She moaned and began to gyrate slowly helping to move my hand around the smooth hotness of her pussy. I stuck my thumb into her hot wetness as she pushed back on it to take it fully. She was getting wetter and wetter as I leaned forward and inserted my tongue into her anus, swirling wetly around and in. My cock was as stiff as I ever remember. She moved her hips as I penetrated her from both ends.
She suddenly stopped, pulled forward and flipped over revealing herself to me completely for the first time. My eyes in a brief second took in her flushed chest and firm breasts with hard inch long engorged nipples, her hard stomach and then to the incredible shaven pussy I had been rubbing and was dripping wetness. In the same spin she grabbed my shoulders pulled me down, melding our bodies while her mouth sought mine and we began a kiss.
I couldn’t believe it, I was tingling and hard as a nail, cock lying over her dripping hot entrance, and our tongues grappling around our mouths. A wild excitement took over my being, my heart beating a million beats a second as it seemed like it would burst my chest while our mouths and tongues worked in time stilling magic. I was floating in ecstasy
We kissed deeply as my cock rubbed her pussy and our bodies surged together. She reached down, breaking the kiss, grabbed my cock and said, “I want you now.”
She guided my hardness and caused it to slide down slightly and I slid into her. All the way into her! She moaned as I went in and brushed her cervix with my unsheathed cockhead.
Deb went still, looked me in the eye and said, “Well now you’ve done it.”
She started to fuck me moving her hips, her pussy kegling me at the same time, caressing my cock more as I plunged in and out. Moving faster, Our kissing tongues rolled as our bodies clung together sweating, moving, sliding. Her hot wetness continuing its motion all around my cock. We were moaning and plunging. I broke the kiss pushed off a bit and used my hips with her's in faster play.
We were smiling, breathing harder in a faster intensity. I felt something gathering at the base of my cock and balls, suddenly the urge surged and I pushed in hard and stayed. At that instant she screamed and came,, a huge flood spilling around my cock and hips as suddenly I feel my semen rise and break through the head of my cock in string after string filling her. My cock was still as far inside as possible as we gripped each other, as we stared into each other's eyes
We collapsed in each other’s arms- looked at each other again and we kissed a slow seductive warm wet post come kiss. We broke the kiss.
She looked at me and smiled saying, “Well, now that wasn’t so hard was it!”
We began laughing together, steeping in our juices, the warmth of our nakedness all around us, as the orgasmic feeling faded to a wonderful memory.
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