I love my family. I have three sisters and a brother – all older than me. My parents spaced us all about three to four 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 pounds of slender gorgeousness, with shoulder length brown hair, brown eyes and 34b breasts. I am the youngest and 6’4”, 160 pounds and with a large cock...when hard.
Beginning when I hit late teens, she flashed me whenever we were alone and a few times when we weren’t, but only I could see. One of the best was the first time I saw her pussy. She had dressed before I came into the room but put on her sheer pantyhose over equally sheer small panties in front of me, raising her skirt to her waist 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 as well which she wiggled while she giggled. 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 sports or work. 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 and backs. I looked forward to these sessions and began to get hard on the rare occasion when I would be in shorts and they were too. The silky feeling of skin on skin was amazing and exciting.
The best session began quite innocently during the summer. 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. 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.
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)?” she asked.
"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?” she asked.
I looked at the floor and mumbled, “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 and it just seems I get nervous.”
“You’re still a virgin?” she 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 while we continued talking about dating and sex. It had been a long day of waiting tables by 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 back massages? I could sure use one!”
It had been a while since I had done this with her so I said, “Sure.”
I had excitement in my voice in anticipation of my warm hands on her hot body and the potential for a fantasy to be fulfilled. We went to her bedroom and she lay on her bed face down, with her head facing left on her folded arms and her eyes closed. 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 and began to rub her neck, making sure I didn’t press my half hard cock against her to ensure she would allow me to continue. As I thumbed her neck firmly, she crooked her head.
She sighed, "Ohh, that feels so good…”
I moved my hands from thumbing her neck to kneading her shoulders, she shifted so he arms were to her sides. I came down further over her mid back and into the middle and then began rubbing out over her ribs in the back.
“Move a little to the sides and up…” she said.
I moved my hand down on her sides with my thumb still on the top part towards her back and began to feel the side bulge of her clothed breasts with my fingers.
"Oh yeah, 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.
“Mmmmmm, yes," she groaned.
I lingered on her soft breasts squeezing and lightly pinching her nipples, my cock was a rock and I had to adjust myself. What a feeling! Her warm, small breasts filled my hands and her hard nipples stretched between my fingers. I was in heaven felling the clothed warmth of my sister's breasts for the first time. As I took a hand off, she lowered herself back to lying on the bed while I rubbed my hands further down her back.
"That’s great!” she said softly, as she raised her backside so that my clothed hard on was lying on her ass crack.
Then, still up on her elbows she said, “I’m getting very hot, could you take my t-shirt off?”
Could I! I stopped and reached the bottom of her shirt 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 now lower to the small of her back. I moved down a bit so I had a better angle and my clothed 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 take them off.”
Who was I to protest?
Somewhat stunned, and in a very trancelike state, I grasped the top of her silk panties and slowly pulled them down unveiling her beautiful ass. I could gaze now on her gorgeous ass and 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. She lowered her midsection back to the bed, while she slightly opening her legs.
She turned her head to the side and said with a big smile, “Are you sure you’re comfortable? You seem constrained.”
To which I stuttered, “I-I- I’m ok…”
I was conflicted. Part of me feared breaking the taboo of incest, while the other part longed to dive in wholeheartedly. I was slowed in my massage, not knowing whether to press forward. Should I make love to my sister or not? I had a fleeting thought of fear of going soft. But she seems to want it, my internal dialogue began. I didn't want to lose her love and respect afterwards. 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. Deb had turned to look at me and my rigid cock as I pulled my underwear down and smiled, putting her head back down on her folded arms. I smiled back and got back into the straddle position. In my nakedness, I straddled her legs and rested my cock on her ass crack.
I went back to beginning my massage at her shoulders and rubbing, kneading hard fingers exploring hot flesh. As I moved down over her shoulder blades, she wiggled her ass slightly, acknowledging the placement of my cock and sliding it deeper in to her ass crack. I sat back with my ass sitting on her legs, withdrawing my cock back to a slight touch of my foreskin on her skin as my hands proceeded down her back and over the cheeks of her ass. I began kneading her ass causing her crack to open slightly exposing the outer portion of her anus and the bottom of her pussy to me.
She moaned and again raised her ass up, as I moved my hands down to her upper thighs and my thumbs brushed some wetness from her pussy. Warm, wet and drooly, 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 gently.
She moaned and said, “Oh, Bill yes, keep that going, 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 and 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 her smooth hotness, as I tucked my tongue between her cheeks and slid over her pucker. I stuck my thumb into her hot wetness as she pushed back on it to take it fully. She was getting wetter and wetter and my member was a stiff as I ever remember. She suddenly stopped and flipped over fully revealing her nakedness to me.
I was stunned. 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 while our tongues danced together. An excitement took over my being with my heart beating a million beats a second. It seemed like it would burst out of my chest while our mouths and tongues worked magic. I was floating in timeless ecstasy!
We kissed deeply, as I my cock rubbed her pussy and our bodies surged together. She broke the kiss, reached down, grabbed me.
“I want you inside me now!" she said.
Deb grabbed my hardness and slid it down from the top of her wet pussy and perched it at the entrance, and I slid into her all the way! She moaned as I went in and touched her cervix with my unsheathed cockhead.
She went still looked me in the eye and said, “Well now you’ve done it!”
She laughed as she started to fuck me using her hips, her pussy kegling me, caressing my cock more as I plunged faster in and out. Kissing tongues wrestled as our bodies clung together sweating, moving sliding hot wetness. I broke the kiss pushed off a bit and used my hips with hers in a faster play, plunging, moving, seeping, sliding; breathing hard with intensity while moaning.
I feel something gathering at the base of my cock and balls. I pushed hard all the way inside and stayed still as my cum began with a huge spurt. Suddenly, she screamed and came. A huge flood spilling around my cock and hips as suddenly I felt my semen breaking through the head of my cock in string after string filling her. She surrounded my cock as her hot cum flowed with mine. My cock was still and hitched as far inside as possible as it all stopped. We gripped each other and we collapsed in each other’s arms. After a second, I rose up looked at her and we kissed a slow seductive warm wet post cum kiss.
When we broke the kiss and she looked at me and smiled.
“Well, now that wasn’t so hard was it?” We began laughing together, steeping in our juices as the orgasmic feeling faded to a wonderful memory.
