Summers are never long enough. Here I was 18 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 actually 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 who would be starting her sophomore year at the local college, Sharon Williams. 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 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 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 despite the fact that 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 A’s from me. Sharon could suck the proverbial golf ball through a garden hose.
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 10-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 40, she could easily pass for 10 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, 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 areolas 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 a 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.
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 20 something bimbo did nothing for Linda’s confidence. Like many women, despite her obvious beauty, she saw only faults in herself. 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 long term commitment.
I pinched myself at the sight of Mrs. Collins on her knees sucking my cock, her full lips painted with bright red lipstick, something she loved to do. When I would get home after being with her and still sporting the telltale traces of her lipstick, I never wanted to shower again.
Fucking two women regularly over the same summer has its pros and cons. The things that Linda taught me I would use 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 with dirty talk, something that took getting used to. It felt like having an aunt or a teacher telling me how to fuck them.
“I love when you lick my asshole, Honey, and then switch back to my pussy. 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. I love it when you put a finger in my ass. It is so exciting.”
And one time 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, Sweetie.” I began to obsess about fucking her ass after that even though I had never done anything like that before.
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. One time she undressed down to only a bra with holes cut out for her huge nipples. Another 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, Sammie,” 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.”
Linda liked to role play as well, usually as a prim and proper spinster who starts out 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 10 inch cock. My bail was worth the time spent in handcuffs.
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.” When we finally got around to sex, it was slow and deliberate. Lots of kissing and teasing until I was begging 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.
Linda knew somewhat about my relationship with Sharon. However, I don’t think Sharon realized I was fucking a 40-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, Sammie. This must be Sharon!”
I did brief introductions, explaining to Sharon that Linda was a friend of the family, and 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.
“Wow, she’s gorgeous. From your descriptions, I thought you were working with an old lady, Sammie. She’s got some serious hooters, too. I bet those would be fun floating in a hot tub!”
“Yeah, you’re not too bad in that department, Sharon. You’ve got great tits.” I hoped diversion would keep her from asking too many questions.
“You know, you seem to have quite a few new tricks in bed these days. If I didn’t know better, I’d think you were taking lessons from an experienced teacher.”
“You’re the only teacher I need. Speaking of which, let’s go to my house for a change. Dad is out of town, and I feel a raging hardon coming on.” I gave her a lewd wink, grabbed her hand, and rose to leave.
You seem in a hurry, Sammie. If I didn’t know better, I’d say you were hiding something besides that big schlong you want to stick in me all the time.
We didn’t talk much on the way to the house. I did not want to have to explain my relationship with Linda Collins, but I was pretty sure Sharon was figuring things out. When we got to the house, it wasn’t long before we were naked and writhing in sweaty sex, however. She seemed to have forgotten about Linda. Still, I worried that if I was not careful, I’d lose out with both women and have to return to my well-used Penthouse and Kleenex.
But this time, Sharon surprised me. She had climaxed in an animated orgasm and climbed on top of me to finish me off. When I announced that I was about to cum, she jumped off of me and pulled the obligatory condom off my unit and quickly replaced it with her mouth.
“Cum in my mouth, Sammie. I want to taste your cum,” she mumbled with a mouth full of cock.
Stunned by this sudden change in attitude, I didn’t argue. I craned my neck to watch as Sharon’s lips covered the plum sized head of my cock and she sucked for all she was worth while pumping my prick furiously. I responded almost immediately.
“Unngghh,” I grunted as a huge blast of cream shot into her mouth. She swallowed and gagged momentarily before continuing until every drop was in her mouth and down her throat. She released me and slid up to kiss me, overflow cum still on her fingers and around her mouth.
“My god you have a lot of cum in you. I swear, you could fill a glass with that and sell it as yogurt.” She licked her lips and then French kissed me.
“What got into you, Sharon. You’ve always said you hate the taste of cum. Not that I’m upset. That was incredible!” I reached up and wiped the last trace of goo from her chin with my finger and placed it in her mouth. She pursed her lips and sucked my finger sensuously.
“I just wanted to give it another try. It really isn’t that bad. In fact, I’d almost go so far as to say you taste pretty good. And you’re the full meal deal! Appetizer, main course, and even dessert.”
We lay there snuggling and giggling while I tried to remove a few freckles from those beautiful tits with my tongue and lips. I sucked on a puffy nipple. “I love your firm tits. Talk about a meal!”
“You know, Sammie, I bet you’d like to suck on Mrs. Collins’ tits. In fact, I think I wouldn’t mind sucking on those puppies. She is really gorgeous. I think I’m a little jealous of her. You seem to spend a lot of time with her.”
“That’s for work. You have nothing to be jealous about. But let me ask, have you ever thought about being with another women now that you mention you like her tits? That’s something I would like to watch!”
“You perv! What is it with men? You’ve never want to watch me with another man, but a woman…oh, that’s different. How about you with another man?”
“Yuck! Not the same thing at all! Lord, help me get that out of my mind. And you are right–I wouldn’t want to watch you with another man, but two women? That’s sexy! Maybe I’ll tell Mrs. Collins you’re interested in sucking those big tits of hers and see what she says.”
“Oh, sure. Go right ahead. I’d like to be there when she slaps you! But back to the main point–women know how to treat one another. I could see me in bed with another woman if she was as gorgeous as Mrs. Collins. We know all the right spots and how to take our time instead of kiss-kiss, stick it in, and shoot a wad–like most men. And I bet an older woman like her could teach me a few things. But we both know that’s just a fantasy that neither of us will experience, so dream on, lover boy.”
And dream on I did. That night, even after our intense session, I had to jack off to the thought of Sharon and Linda in a passionate embrace while I encouraged and egged them on.
Eventually, summer was winding down, and I realized my good times were coming to an end. I had been accepted at a junior college in another county, so visits home would be infrequent. I had resolved that I would do better academically and after two years get accepted into a state college. In the meantime, my days with Linda were numbered. We hadn’t actually had sex for a couple of weeks and things seemed much more businesslike between us. I sensed that she was relieved that I would be leaving.
I had finished for the day with some painting, and as I was cleaning up the brushes in the garage, I noticed a note on the work bench. “Sammie, please stop by the house when you are done.” I figured Linda would probably give me my last paycheck, but secretly hoped she would have some wild fantasy in mind instead.
The kitchen door was open and I knocked on the screen door. Linda was wiping up a countertop. “Hi, c’mon in. I’m just finishing here.” She directed me to a chair at the kitchen table.
I sat and watched her. She was wearing short shorts and a tank top. Those boobs were wonderful, but Linda also had a great ass and legs. Smiling, she turned and sat across the small table from me. I was leaning with my forearms on the table and she took my hands in hers and bent down and kissed them.
“Sammie, we need to talk.”
Oh, oh. This was the conversation I had been dreading. I could feel it. “Sure, what’s on your mind?”
“Honestly? You’re on my mind. In fact, I can’t get you out of my mind. This has been a wonderful summer for me in many ways and you are mainly the reason. When my husband left me, I thought it was the end of the world, and then you came along. You were just what the doctor ordered. I was lonely, depressed, and felt like my world had collapsed overnight. Then you came by and like a breath of fresh air, changed everything. You’ve been wonderful in every way for me. You are helpful and considerate, not to mention sweet. Of course, the icing on the cake has been the wonderful sex. You made me feel like a teenager again, except for the days when I could barely walk. That big penis of yours is something, and just the thought of it makes me squirm a tad.”
I smiled at the thought of my fat member buried in her juicy pussy doggy style, which she liked, watching it slide in and out as she wiggled her perfect ass in appreciation.
“Linda, I think I know where this is heading, but just let me say that if anyone is grateful, it’s me. You’ve been wonderful during the shittiest time of my life. You don’t know the worth of someone until they’re gone, and mom’s passing crushed me. I don’t know what I would have done without your guidance. Yeah, the sex didn’t hurt. At the very least, you got my mind redirected with your advice and the realization that I was making love to the sexiest woman on the planet on a regular basis. You taught me things that I’ll remember for the rest of my life.”
“I’m glad t hear that, Sweetie, and I’m flattered that you think an old lady like me can be sexy. I questioned our relationship much of the time, mainly because of the situation with your mom. She was a good friend, and even though you needed a distraction, the guilt was overwhelming at times. I think I was in as much denial as you for much of the summer, but after your mom died, I couldn’t help but second guess my motives. Was I trying to help you or just satisfy myself? I looked forward to each day you came to the house, and during breaks in the action, I had to find ways to satisfy myself. My vibrator falls far short of that magnificent cock of yours, though. I’m ashamed to admit it, but when I took pictures of you that time I measured it, I saved them to look at when I wanted to stimulate myself.”
I think I actually blushed at the thought of Linda staring at a picture of my cock while she pleasured herself with a vibrator.
“I’m flattered. But I’d prefer you used the real thing.”
“I’m the one who’s flattered. The fact that you took an interest in me made me feel years younger. But to the point of all this–you’re getting ready to leave for college and we both knew that no matter how either of us felt about our relationship, I’m old enough to be your mother. It wouldn’t be fair to either of us to expect this to go on forever. But I also didn’t want you to just leave without this discussion. Sammie, I’m not sure if I’ll still be here when you come home from college. I need to return to work after sitting around all summer. I have a job offer but it requires moving to another state. That doesn’t mean we’ll never see each other again, but it does put more distance between us. Regardless, I’ll always cherish this summer and I will never forget you.”
This was worse than I thought. I almost panicked at the thought of never seeing Linda again.
“How about this? No pressure, but I’d still like to see you from time to time. We’ll only be a phone call away and if you decide enough is enough, I’ll honor that. I will never forget this summer either, probably for some of the same reasons as well as reasons of my own. But either way, you’ve changed my life, and for the better. If I’ve made you happy in any way, I’m ecstatic. You are unbelievably gorgeous and sexy on top of being smart and funny. I get hard just thinking about our times together.”
Linda stood. “Of course we may be able to see each other from time to time. But the circumstances could be different. I just don’t know. Oh…” she paused in thought. “Come here and give me a hug.”
She opened her arms waiting for me. I stood and we embraced. She pressed her tits into me and I squeezed her tightly.
She whispered in my ear, “Do I feel something trying to free itself? Why don’t you come with me one more time. I have a little surprise for you.” She smiled a devilish smile. “Do you have time or do you need to leave?”
“Wild horses couldn’t make me leave.”
Still holding my hand, Linda only said, “Then follow me.”