Summers are never long enough. Here I was, eighteen years old and headed for college in September. What could be better? Ok...it was only a junior college, and I was on probation since my high school grades could have been better. I had virtually no money even though I worked off and on most of the summer for a neighbor, Mrs. Collins. It was a dream job--trimming trees, mowing lawns, doing handiwork, and fucking her brains out. I didn't get paid for that last part...at least not in cash.
With the death of my mother after a long battle with cancer, Dad and I had pretty much become used to a bachelor's lifestyle, eating whenever and whatever and not always healthy. Fast food chains provided much of our nutrition, and dad looked the part. When Mom was alive, meals were always healthy and colorful: greens, fruits, legumes, and lots of chicken and turkey. With her gone, beef reigned supreme with lots of starches and sweets to round out our meals. Both of us gained weight, but my youth and metabolism kept my body in reasonable shape. Dad bloated and looked like a heart attack on alert.
I had been juggling my social life around two women: Linda Collins down the street and a neighbor girl, Sharon Williams, who would be starting her sophomore year at the local college. Mrs. Collins hired me to help around her house, partly because she was a friend of mom and partly because she was divorced and couldn't do a lot of the basic household maintenance. As it turned out, she also was hungry for some personal physical maintenance that I was happy to provide.
Sharon and I had dated off and on, but it turned out that our shared interest was pure, raw sex. She liked to fuck, and I was happy to oblige.
Linda Collins, as attractive as she was, was lonely and horny. After her husband left her for a younger woman, she became socially reclusive and, in effect, became a 40-year-old, good-looking spinster. Our affair turned her into a cougar of sorts with a voracious appetite, at least for a while. When my mother died, she cooled things considerably and wanted to be more of a counselor with me. I appreciated the maternal instincts in her, but really, I mainly wanted to sink my cock into her and play with her luscious breasts. As the summer wore on, she seemed more reluctant to engage in our sexual escapades even though she practically salivated at the sight of my huge cock when I'd pull it out.
On the other hand, Sharon and I were just in it for the sex even though our initial attempt at copulation resulted in my premature cream pie in her unprepared vagina. Only after a second attempt did we find mutual satisfaction. Sharon wanted to fuck me whenever she was healed from our previous marathon fornication. I happily serviced her and always wore a giant prophylactic, or raincoat, as she called it, during actual copulation. Thankfully, she preferred my prick unadorned for fellatio, something she had apparently majored in during her first year in college. She earned nothing but high marks from me. Sharon could suck the proverbial golf ball through a garden hose. And she loved to do it. When she wasn't sucking the life out of my cock, we were usually tangled in sweaty gymnastic sex.
Both women were goddesses as far as I was concerned. Sharon had the toned body of a gymnast, which she was through high school. She was petite overall, maybe 5'4" with a mop of red hair, freckles, and a nice pair of tits. Her freckles were everywhere, a source of displeasure for her, and I did my part by attempting to lick them off her tits whenever I could. Because of her training in the gym, her flexibility was a bonus. She could do the splits while entertaining my ten-inch cock, and I especially enjoyed fucking her with her legs pinned behind her ears.
Mrs. Collins was beautiful but by a different standard. At forty, she could easily pass for ten years younger, especially when her blonde hair was in a ponytail and she was wearing a ball cap, but when wearing a slinky dress and heels, she looked like a movie star. A bit taller than Sharon but nearly as fit considering her age, she ran and did yoga regularly to keep in shape. She had a fuller figure, marked by a pair of magnificent tits capped with huge pink areolae and pencil erasure nipples. I loved nothing more than suckling on those huge boobs when my cock was buried in her. She had just the start of middle-aged spread, but nothing of any consequence. What she did have was decades of experience and frankness that caught me off guard. She taught me previously unimaginable things to do to her during sex and was not afraid to tell me exactly how to do it down to the last detail. Her playfulness and willingness to experiment were in part because our age difference mandated we could never be committed to a serious relationship. Sex with her usually had a tender side to it, but then other times she begged me to fuck her like a jackhammer.
"Enough lovemaking, Sammy. I'm ready to cum. Fuck me like you mean it, Honey. Let me feel those big balls slam into my ass and drive that big fat cock into my pussy. Give it to me, Sweetie."
Why men weren't beating a path to her door was beyond me, but I attributed it to intimidation and isolation. Her asshole husband's departure with a twenty-something bimbo did nothing for Linda's confidence. Like many women, despite her obvious beauty, she saw only faults in herself. And the neighborhood wives tended to gossip spitefully about her as a defense mechanism which only added to her isolation. Consequently, she turned down dates except on rare occasions and became a homebody. It was my unbelievable luck to open that door, probably because I was a cute neighbor kid, and I posed no threat of serious commitment. She was able to get all the sex she needed from me with no strings attached. And... she could direct me to please her every whim and fantasy. I was what you would call a devoted student and putty in her hands.
One afternoon when my chores were finished and we were in her bedroom, she looked me in the eye with a serious expression.
"You know, Sammy, that our relationship can go no further than this? I know how boys can get all gaga over a woman, but keep in mind that I'm old enough to be your mother. I love having sex with you and think the world of you, but please don't get any romantic ideas. The sex is too good, and as long as we can keep it that way, I think we will both be happy."
"I understand, Linda. I know I'm the luckiest guy on the planet to be able to just hang with you. I would never do anything to jeopardize that. You've made this the best summer of my life."
I looked down and pinched myself at the sight of Mrs. Collins on her knees returning to my cock after my reassurances. Her full lips had painted a bright red ring around my shaft, something she loved to do. When I would get home after being with her, I would stare at her trademark on my cock and relive those moments. I never wanted to shower after.
Fucking two women regularly over the same summer has its pros and cons. The things that Linda taught me were later used on Sharon, and they were appreciated. Linda was the perfect teacher: patient, caring, and exciting. She gave me explicit instructions when I was eating her, correcting and coaxing me with dirty talk, something that took getting used to. It felt like having an aunt or a teacher telling me how to fuck them at first, but I learned to love her detailed teachings. She knew that her use of explicit language only increased my excitement.
"I love when you lick my asshole, Honey, and then switch back to my cunt. Don't forget my clit. Just lightly suck on it for a minute while you fuck me with your fingers. Why don't you get your finger slick with my juices and then slip it in my ass? My ass craves a slick finger from time to time. It is so exciting and nasty. Just your fingers, though. Don't get any ideas about putting anything else back there." She giggled and wiggled her ass to taunt me.
But on one occasion midway through the summer, she added..."I bet you'd like to stick that big cock of yours in my ass, wouldn't you? Well, that's a special place and you're just going to have to wait. But for now, you can put your tongue in there, Sammy. Your tongue is plenty big enough for my tight ass."
That planted the seed. I began to obsess about fucking her ass after that, even though I had never done anything like that before. Anal sex had never seemed attractive until Mrs. Collins used it as an enticement for future sex.
Of course, Sharon didn't talk to me that way. But she didn't need to. With her, sex was less talk and more action. And even though both women issued veiled complaints about not walking straight after having sex with me, for Sharon it was real. We fucked like monkeys, always ending in a sweaty tangle. By the time we were done, we were both gasping for breath.
Sex with Linda was more subdued. Sometimes she would slowly strip--revealing sexy lingerie underneath her day-to-day clothing. As much as I liked to see her naked, we sometimes fucked with her dressed in a tight-fitting bra and a thong pulled to one side. That excited me as much as anything. One time she called me from the bedroom where I found her naked and blindfolded, her legs and arms tied to the bedposts with heavy yarn.
"Oh, Sammy," she begged in a melodramatic voice. "Please don't take advantage of me. I've been tied up as you can see, and I'm helpless to stop you if you have any evil thoughts."
Mrs. Collins occasionally liked to role play as well, usually as a prim and proper glasses-wearing spinster who starts with her hair in a bun but turns into a wild beast at the sight of a cock or with a single kiss. One time she greeted me in a police uniform, a holdover from a Halloween party as it turned out. She arrested me for having an unregistered weapon, a ten-inch cock. My bail was worth the time spent in handcuffs as she had her way with me.
Most days when I was working at her house, she would disappear later in the afternoon and I would find a note with instructions like, "When you are done mowing the lawn, meet me in the bathroom. Be sure to remove your clothes first."
Typically, when we finally got around to sex, it was slow and deliberate. Lots of kissing and teasing until I was begging her to let me fuck her.
But toward the end of the summer, she seemed to cool off and just wanted to talk more and more. Mom was long buried, but I think her death affected how Linda felt about me. During mom's final days, Linda used sex as something to take my mind off the fact that I was about to lose my mother--sort of a placebo for depression. But later she would find excuses to just cuddle or talk. So, I spent more time with Sharon who would have been receptive to sympathy sex but just wanted to fuck for any reason. She loved sex as much as I did.
Mrs. Collins knew somewhat about my relationship with Sharon. However, I don't think Sharon realized I was fucking a forty-year-old divorcee.
"She's just my boss," was my standard answer to her queries. Then one day in August I was with Sharon at the mall, and we ran into Linda.
"Oh hi, Sammy. This must be Sharon!"
I did brief introductions, explaining to Sharon that Linda was a friend of the family and that I was helping her over the summer with chores. Linda was effusive with compliments for Sharon, as well as what a "cute couple" we were. Sharon smiled and was cordial through it all, but eyed Linda suspiciously, especially when she walked away.