21
Kelly was turning 30 years old. Like many other women her age she had hopes and dreams of what her third decade might bring, but what Kelly definitely didn't expect when she turned 30 was to be a single mother for the second time.
Kelly met her first husband, Roger, in college, a friend of a friend who stepped in one night when her planned date bailed on her. Kelly didn't get out too much, always head down in her studies, and she had gone all out for this date. She did her hair, wore her tightest pants and her nicest blouse, even borrowed a push up bra from her roommate to make sure all her assets were on display.
She was excited. She had met her date at a party a week or so ago, a party she almost didn't go to, save for the urging and encouragement of her best friend Sandy. The opposite of Kelly, Sandy was a social butterfly, far more interested in the more enjoyable side of college life. That's not to say Sandy wasn't a good student though. She was the gifted type who could party through the weekend and not remember any of it, while also being ready to go for an exam on Monday. Sandy and Kelly were inseparable, and Sandy had been there to help Kelly broaden her horizons ever since day one.
Sandy and Kelly met the night of the first formal dance at their college. 18 years old, and away from home for the first time, Kelly was excited to share a luxurious night out with her boyfriend. High school sweethearts, they were both shy virgins when they got together. They made love for the first time one summer night after graduation, and even though it was short, and not entirely pleasurable for Kelly, it excited her to no end. She was now a sexual person, a woman, and she thought she had found her person. They had shared this intimate, intense experience, and she was sure the connection they now shared would carry them into many years of love.
Unfortunately what it brought was only a couple more awkward sexual experiences together in between shifts at their respective summer jobs and an uncertainty about where their relationship was headed.
Their last night together had been enjoyable enough, seemingly for both of them.
"Do you think maybe you could suck my dick next time?" He asked as she climbed off his softening penis, and back into the passenger seat of his car.
Kelly was taken aback. Admittedly she was a little hesitant (one might even say afraid) of putting a hard penis in her mouth, of giving up that much control, but as she looked down at herself, plump tits still exposed and red from sucking, bunched up skirt barely covering her wet, swollen pussy, she couldn't help but wonder what she had done wrong. She had taken his cock inside her and milked him with her body until he exploded, and didn't even complain or feel cheated that she once again hadn't cum herself. But apparently he was still feeling unsatisfied.
"Uh, sure..." she said, trying to organize all the thoughts swirling in her head, "...I don't see why not."
There wouldn't be a next time before they both left for college, and Kelly would be lying if she wasn't slightly relieved. Not so much because she didn't want to suck his dick, she was willing to try it if that's what he wanted, but more so because something felt off. She couldn't put her finger on what it was, but it was something.
College started, and Kelly began focussing on her studies. She did her best to talk to her boyfriend as often as possible, but as these things go, nightly turned into twice a week, which turned into weekly, which turned into bi-weekly. The dance was coming up however, and Kelly saw it as the perfect opportunity to rekindle things. They had both been focused on school (or so she thought), but the dance would be the chance for them to focus on each other, and she was ready. If he wanted his dick sucked, she was going to suck his dick.
Having a boyfriend who went to a different school, Kelly wasn't on the market, but she wasn't dead either. She still had needs, and as she was a great student, her regular self-pleasure sessions became erotic study sessions. She touched herself to a wide array of "research material" she found on the internet, and as her pussy began to develop a pavlovian response to the images of a hard cock being loved on by the mouth of a beautiful woman, she began to understand it. To want it.
She was looking forward to it. She fantasized about feeling the spongy head with her tongue, about feeling his hard shaft slide between her lips. She wondered how much of him she'd be able to take in her mouth, what she'd be willing to do when it came time for him to shoot his load. She wanted nothing more now than to suck her boyfriend's cock, and she was going to rock his world at the dance.
Then the phone call came.
Sandy was on her way to the showers, the first step in preparation for what she knew was going to be an amazing night. She was getting ready to go to the formal dance with her boyfriend Don, and she wanted everything about her look to be perfect. Sandy and Don had met at the local bar the first week of college, and they had been joined at the hip ever since. Or, more specifically, joined at the crotch. Sandy was no virgin when they met, she had her fair share of fun in high school, but there was just something different about Don. A different feeling. A different energy.
Don was a junior, and wasn't looking for a new relationship. He had just had his heart broken and was out with some friends, looking only to hang out and have drinks, when across the room his eyes fell on the most gorgeous thing he had ever seen in his life: a wild mane of dirty blonde hair; a smile that could only be described as lusty; a pert, tight butt, and two, large, supple breasts encased in a tight, low cut shirt, boiling over with deep cleavage.
Suddenly he found himself wondering what those breasts felt like in his hands, what her nipples tasted like, what she sounded like when she orgasmed. He found his way over to her by the bar, where she accepted the drink he bought her with a smile. By the end of the night he found himself balls-deep in her pussy, her lovely body bent over the hood of a car. He got to feel those breasts, taste those nipples, and hear those orgasmic sounds as she spasmed around his hard cock.
Don's balls began to boil, and as he announced he too was going to cum, he only then realized they were too caught up in their lust to remember a condom, but it was no matter; without missing a beat after his climactic announcement, Sandy breathlessly offered three words back: "In my mouth." This sent a surge to his balls, but it was the fourth word she choked out after catching her breath that sent him careening over the edge: "...please."
His cock stiffened harder than iron, and in almost a single, smooth motion, he slipped his cock out of her pussy, and Sandy melted down to her knees, taking him into her mouth. Don felt one hand on his balls and another gripping his hip, and after no more than three or four bobs of her head, his whole body tensed, and this girl he'd just met received a mouth full of hot cum.
She looked in his eyes as she swallowed, and suckled gently on his softening tip as his breath came back to him. They both smiled. They both laughed. They both knew this was something special.
That night was only the first of many that Sandy and Don spent together. That night had been erotic, electric, dirty and explosive, which is exactly why Sandy put the breaks on the physical stuff for the next couple weeks. Don's cock was perfect for her, and he had made her cum harder than any man had at that point, but she wasn't just looking for a quick fuck from this guy--she wanted to see if their chemistry extended outside the bedroom as well.
Don was a total gentleman on their much more chaste followup dates, never pushing, never pressuring, just happy to spend time with Sandy and get to know her. It was this chivalry, on top of the fact that he was legitimately an amazing guy, that sent her home soaking wet, where she would attack her dildo with purpose, cumming long, hard, and loud into her pillow.
They both knew what was in the air the night they went to watch their mutual friend play basketball for their college team. Few words were said, but few words were needed, as the smiles on their faces spoke volumes. After saying goodnight to their friends, they drove silently back to Don's apartment, slipped into the bedroom, and made long, slow, passionate love throughout the night.
This time when Don gasped, and his balls pulled tight to his body, there would be no pulling out. Sandy's legs gripped him closer than ever, and she felt every pulse of his spasming cock as her body milked his cum into hers. Breath left her body and with Don's bare cock still pumping inside her, Sandy began to cum as well. It would be the first of many barriers brought down between them, and soon they would begin to explore every corner of each other's desires and fantasies, something they would continue to do deep into their eventual marriage.
Sandy was excited about the dance because she was planning to explore one of those corners of fantasy that night--she wanted everything to be perfect, because she was going to give Don her anal virginity. She had had fingers, toys, even the stray tongue in there in the past, but she'd never committed to letting a cock penetrate her ass, and that night she was ready to give it to Don.
As she made her way toward the showers she thought about the evening, about the act. For the first time in a while, she was nervous. She practically knew Don's cock front to back at that point, but still, anal was something totally new for her. His dick was long, and it was thick, and her ass was very tight. She wondered if he'd be able to fit it all in; what it would feel like for him to fuck her; what it would feel like when he came.
