I was not only the youngest of five children, but my four older siblings were all girls. I had many of the advantages of being the youngest--my sisters treated me like a pet; I was smothered with mothers. I also had many of the disadvantages. Like many of the youngest, I had more than my share of hand-me-down clothes. With all older sisters, my clothes were often effeminate. If I wanted blue jeans, I had to endure girlie stitching and cuts, or shirts that buttoned on the wrong side.
At times it felt like I had five older sisters. The sister closest in age, just a year older, Ellen, had a best friend, Sue, who virtually lived at our house. Sue's family was what is called "dysfunctional" -- divorced parents, a step father with whom she had a difficult and complicated relationship, a distant and alcoholic mother. For my parents, one more kid in the house was hardly noticed. My three older sisters were all well-behaved. Based on their experience with the first three, my parents trusted their kids, and tended to
be permissive because the kids had never given them cause not to be. But sister number four, Ellen, was the wild one, and she and Sue were another story entirely.
Whereas the three older sisters were all good students, and acted responsibly, Ellen and Sue were "boy crazy," and were constantly getting into trouble. They were both exceptionally pretty girls, and they loved to push the limits, wearing make-up long before most girls their age did, bleaching their hair blonde, dating older boys, coming home late. They wore the shortest miniskirts and during the hot pants fad wore skimpy skin tight little short shorts that failed to cover the bottom third of their bottoms. Both were sent home from school on more than one occasion to put on more modest clothing. Boys were constantly swarming around them. They were also a lot of fun, and everyone, my parents included, tended to laugh off their transgressions.
I had a special relationship with Sue from childhood. She was sort of like another older sister, but we both knew she wasn't a real sister, and she flirted with me constantly throughout my entire childhood and adolescence. Sue came with us on family vacations. I got to see her in bikini bathing suits, in various stages of undress, and the object of her constant sexual teasing. Sue enjoyed knowing that I was in awe of her. She immediately recognized her power over me, and loved to exercise it. She never ever went and
got something for herself if I was near. She would ask me to get her a pencil, a soda, change the channel (this was before remote control televisions), etc., and I would happily hop at her beck and call. She also quickly discovered and encouraged my voyeuristic tendencies. She noticed me watching her constantly, and often she facilitated my hungry appetite to see her. She frequently slept at our house, and would walk around the house--like my sisters--in her nightgown. She often wore a thin, shortie, translucent one,
and I loved watching her breasts through the material and to see her little bikini panties. She would strut around me, lean forward and watch my eyes drop to her chest, and, her favorite, to find a way to flash glimpses of panty crotch by opening and closing her legs.
Once when I was alone in the room lying on the floor watching TV, Sue came in to tell me something. She came in and stood right over me, straddling my head with a foot on either side, allowing me to look straight up the length of her legs to see the breathtaking view of her panties from directly underneath. It was an indelible image that I played over and over again for hundreds of masturbatory orgasms.
One time when Sue needed to quickly change her clothes, she "borrowed" my room for a couple of minutes. When she rushed out, she had left her cute little pink panties in a pile on my bedroom floor. When I entered my room, I shut the door (we didn't have locks on our doors) fell to my knees and immediately began smelling and feeling Sue's panties on my face. Within minutes, my pants
were undone and I was beating off, licking the crotch of her still-warm panties. Just then the door flew open.
"Caught Ya!" Sue cried. I was mortified. But Sue just closed the door and hopped up on my bed. "I was just wondering what you might do if I left you alone with my panties," she said, giggling. I was still on the floor with my erect penis exposed, embarrassed and confused. "Do you wanna keep 'em?" she asked. "Yeah," I stammered. "Well, you have to say, 'pretty, pretty please, with sugar on top," she
said. As she said this she sat up on my bed and crossed her legs. I was eye level with her knees. I started to repeat the words and try to zipper my pants at the same time. "Don't zip your pants," she said, "I want to see you play with yourself." As she said that she uncrossed her legs and parted her knees slightly. "Do you like looking at me, Jimmy?" she asked. I had lost my voice, and could only nod my head. "Do I make your penis all hard?" I nodded again, my eyes focused on her thighs and the hem of her
short skirt, trying to catch another glimpse up her skirt. She then scooted back on my bed, with her back against the wall, and lifted her knees up to her chin. Her panties now completely and gorgeously exposed.
"Be my sugar baby, Jimmy, make it spurt. I want you to make it spurt," she said. Still on my knees, my eyes glued on her thighs and panties, I spurted and spurted.
"Wow," she said. "That's so cool." She hopped off the bed. "Here's another present for you, sugar baby. Think of me tonight."
With that, she wiggled out of the panties she was wearing, and I now had a special nickname and two of Sue's panties--the beginning of a lifelong collection.
My sister Ellen sometimes saw me as a nuisance, but Sue always seemed to be happy to have me around, and loved the adoring attention I paid to her. Even Ellen, however, found a use for me. As the girls had the boy crazy reputation, my parents thought the situation would stay safe if I was included as a little brother chaperone when they went on dates.
This was the era of drive-in movies. Ellen and Sue would double date, and I would be assigned to be the fifth on the dates. Ellen would always take the front seat with her date, and Sue, her date, and I would be in the back seat. The guys would buy me my fill of popcorn and soda, and I would be the only one even pretending to watch the movie. The two couples would begin making out immediately, and the necking would continue for the next two hours. I would sit quietly, trying to keep out of the way of legs and feet. But the movies held no interest for me either. I perfected the art of looking out of the corner of my eye. My head was pointed straight ahead looking at the movie, but my attention was focused entirely on watching Sue making out. I loved seeing the guy (they were interchangeable) working his hand under her shirt and squeezing her breasts.
Often, Sue would extend her foot into me or end up resting her feet on my lap. Sometimes I would lightly touch her with the back of my hand, always afraid her date would notice me touching her, and that I might get in trouble. Sue would also sometimes rub my hard on with her foot while making out with her date. Sue also was quite a drive-in-movie kisser. I would watch her tongue working in and out of the guy's mouth, watched her suck on his neck and chest, and then would watch the crescendo as they guy would beg for her to suck or jack him off (actual intercourse seemed to be considered off limits by mutual understanding). But short of penetration, they really used their hands and mouths, and both Sue and
her date (as well as Ellen's and hers--though I only took a passing interest in them) always had at least one orgasm each.
My job was always to bring Kleenex along so the girls and their dates could clean up afterwards. Sue had the great ability to suck a guy's cock and simultaneously catch my eye and smile at me. The way she could smile with a cock in her mouth was a delight.
Ellen tolerated my presence as a necessary price to pay for her pleasure. But for Sue, my presence actually seemed to enhance her pleasure, and I think she genuinely liked having me along as an appreciative audience. Sometimes after an especially steamy night of necking, Sue would give me a "present" -- her warm, damp panties. The aroma would be overpowering. Sometimes there
would be cum stains where her date had rubbed against her. I would go straight to bed when we got home from the drive-in and have my own little party with Sue's panties.
When she didn't spend the night at our house, but returned late to her own house, I had the job of escorting Sue on the walk home to make sure she got in safely. She usually did all the talking, and I just enjoyed being her protector. She would tell me to make sure she got into her room safely, and told me to wait outside to see the light go on in her bedroom. Then, knowing I was watching from outside, Sue would always get undressed with the lights on and the shades open. She would peel off her shirt and pants or
skirt, and walk around back and forth across the window several times in her bra and panties.
Sometimes I would watch her examining different nightgowns for the night. She always made a production out of unsnapping her bra and wiggling into her nightie.
I would always rush home so I could masturbate.
I had another chaperoning duty with Sue. Often, she would call me to her house or have me accompany her home when her Mom was out and only her stepfather was home. She had a strange relationship with him that I never entirely figured out. She wanted me there clearly to protect her from his sexual advances, yet she seemed to be the one making all the advances. I watched as she flirted outrageously with him, and I'm convinced he never laid a finger on her. Just as Sue called me her sugar baby, she called her
stepfather Sugar Daddy. She would tease him, wiggling her bottom at him, flashing her panties, pouting in a little girl way, sometimes sticking her tongue out at him, giving him clear views down her blouses or nighties. I'm pretty sure she played him the same way she played me--exercising her power over him, encouraging him to masturbate, leaving him little presents like her panties.
I think her stepfather and I were both in awe of Sue--she remained an untouchable sexual icon for both of us.
I myself never dated in high school. I remained shy around girls, but I was also devoted to Sue, and really had no interest in anyone else. I understood Sue to be completely unobtainable. I knew she would never be my girlfriend and that I would never take her on a date myself. But as long as she would let me watch her on her dates, call me her sugar baby and have me "protect" her from her Sugar Daddy, I was happy.
Even when I was not needed as a chaperone, Sue would help arrange for me to have a good spot to watch her with her boyfriends.
She even let me watch her lose her virginity. It was homecoming, and Sue's date was one of the high school football stars. I had watched all afternoon as Sue and Ellen primped and preened. I loved watching Sue get ready for her dates, and this one was special because they were really getting dressed up. Watching Sue put on her make up, brush her hair, apply perfume, fiddle with her stockings, was pure delight. Sue told me that after the prom, she and Ellen were going to sneak the guys back to her house.
By that hour, her mother would be passed out drunk and her Dad worked an early morning shift so usually had to go to bed very early to get up before sunrise. Sue had given me a key to sneak in at a set time.
My job was to act as lookout in case one or both of her parents woke up. I could perch on the top steps of their finished basement, where they had a little rec room. If the parents appeared, I was to serve as a noisy decoy, telling them I was here with Ellen and Sue. The two couples in the rec room wouldn't
notice me since the stairway had its own wall. I watched as Ellen and Sue and the two football players drank and fooled around. It was especially erotic seeing how dressed up and adult looking the girls were with their hair up fancy, and their pretty, but sexy gowns. Both went for the strapless look with some sort of push-up bra that practically thrust their pert breasts into the faces of anyone in the vicinity.
I watched wide-eyed, as the two couples progressed from horseplay to necking to fumblings with clothing to out-and-out fucking. It was like watching a strip tease. So many layers of clothing and underclothing that Sue's date had to navigate, including garter belt and stockings.
After they lost their virginity, late-night rec room escapades became more common, and I always had the job of lookout in case the parents woke up. "Lookout" -- what a perfect word for me, the young voyeur. I had found my calling.
All good things come to an end, though for me it was just a beginning. During Sue's senior year in high school--my junior year--I found her crying one day. I went to comfort her, and discovered that she was pregnant. Abortion was not an option that we were even aware of in those days and in that place, nor an option that we had even considered. The options for girls in that time and place wre marriage or putting the baby up for adoption. Sue didn't even know who the father was and had no interest in marrying
any of the boys she had been with anyway. Seeing how miserable she was, and falling even more deeply in love with her, I asked Sue to marry me. At first she looked stunned and uncomprehending. I told her that I loved her and would do anything for her.
She told me that she didn't love me "in that way." But I said that was OK, that I had enough love for both of us, that I would take care of her and the baby. To make a long story short, we got married, against our parents wishes. An 18-year-old pregnant wife and a 17-year-old inexperienced, virgin husband.
The first few years were rough, but I was true to my word, and devoted to both Sue and our baby girl, Ellen. Sue became a waitress, but had trouble holding a job. I started out just taking care of Ellen, but, one thing led to another, and I became a licensedday-care provider taking care of a bunch of babies and toddlers, and found that I really enjoyed it and did a good job at it--although in those days it was almost unheard of that a man would be a day-care provider. But people knew and trusted me, and it worked out well.
Conventional waitressing was not Sue's thing, and she became a cocktail waitress, where she started making good money from tips. She would work late into the night, early morning, and sleep until noon or later, whereas I would go to bed early and be up very early for the parents to drop off their children. We hardly saw each other, except during the quiet late afternoon after the parents had picked up their kids and just before Sue was heading off to work. At those times, I loved watching her get dressed for work. She
wore a short cocktail dress, a low-cut, tight blouse, stockings, heels, as well as eye shadow, lipstick, teased hair. Very sexy.
Actually, pretty slutty. Even as husband and wife, we didn't have a conventional sexual relationship. I was still the voyeur. Sue would let me watch her getting dressed. Even though I could have done it openly, I preferred to do it in a sneaky way, to spy on her, even though she knew all the time I was doing it, and enjoyed putting on a "show" for me.
I usually masturbated to orgasm every day watching her get ready for work.
I tried to have normal sexual relations with Sue, but she never showed interest in me as a sex partner. But as our relationship developed, she seemed to get more and more satisfaction by humiliating me,especially when she was drunk, which was most of the time she was awake. I would beg her for sex, and she found ever more devilish ways of rejecting me. I think she loved my begging and groveling. She liked having me serve her hand and foot. I don't think Sue ever once rinsed out a dish, put an item of
dirty laundry in a hamper, of so much as cooked a piece of toast. I did everything.
When she was drunk she would either get more abusive toward me, or more affectionate, or both. It was when she was drunk that I would be able to get most physical with her, giving her a lot of oral attention, culminating in extensive ass and pussy licking. After work massages became a regular feature of
our love life. She always came home from work drunk. I would undress her, if she wanted a bath or shower, provide them for her, and lotion and oil her body until she would pass out. At that point, I would take voyeuristic pleasure in examining her sleeping body. I could position her legs in whatever way I wanted, snuggle up for a close up view, and masturbate to orgasm.
Many nights, Sue would come home with other men's cum in her pussy or in her pubic hair or down the inside of her thighs. Depending on her mood, I might be treated to tongue cleaning duty, especially if I begged and pleaded enough.
Eventually Sue tired of family life and ran off with someone else, breaking my heart. She's the love of my life. I don't think I could ever find another person who understands me as she does. Even as she rejected me, she did it in a way that showed acceptance of who I am, and who I have become is very much Sue's own creation. So, while she will always be Runaround Sue, I am a one-woman man. I have tried to have sex with other women, but have never been able to sustain an erection with another woman or achieve an orgasm with another, even when masturbating to pictures or videos, I can't cum unless I have Sue's image in my mind.