Kate had not seen Neil since they her senior year of high school. Her prom date senior year, they went their separate ways for college and Neil missed each other at the high school reunions they each attended. Neil friended Kate on Facebook earlier in the year and they had traded a few messages. Neil now lived in Dallas and Kate found herself headed there to see a friend.
She got in on a Thursday evening and would not see her friend until the following day, so she mentioned to Neil she was going to be in town and free on Thursday for dinner. It happened that Neil’s wife was out of town visiting family, so he happily agreed to meet Kate for dinner.
After she landed, Kate grabbed and Uber to her hotel—the Westin downtown. Her mind wandered, thinking back on their prom night. Neil was a nice guy, everyone’s friend and when Kate and her boyfriend had broken up a couple weeks ahead of the prom, Neil happily stepped in to take her. They had a fun night, dancing and laughing and when they left the prom, Kate asked Neil if he wanted to go down to the point, the place where kids from their high school went to “park”, Neil seemed surprised. “Do you want to?” Kate asked. “Um, sure,” Neil responded, sounding nervous.
Although Kate had been a good student and an athlete, she had a bit of a reputation. Several guys claimed to have benefitted from her oral skills and other guys had claimed that she “likes to fuck.” Much of it was true. Although Kate had been with her boyfriend for over a year, she did start early, giving blowjobs to a few boys in her neighborhood and on a couple of dates, and having sex with two older boys before she met her most recent boyfriend. She was very active with her boyfriend. His mother worked so she spent many afternoons at his house “studying.” Even though he had cheated on her and was pretty much a dick overall, she missed the sex.
Neil found a spot at the end of the road, away from several other cars that already had made it there. He felt Kate’s hand on his leg. She looked at him and smiled. He smiled nervously back. Kate was not bashful and her hand slid up his leg towards his crotch, the side of her hand brushing against his balls. Neil felt himself getting excited. Kate leaned forward and kissed him. Slipping her tongue into his mouth, her hand now feeling around for his cock through his pants. She could tell it was large and felt it getting hard as she touched him. This excited her.
As they kissed she fumbled with the buckle on his belt until she was able to unbuckle it and then find the top button of his Neil’s pants, which were now sticking out prominently. She unzipped him and, in the moonlight, could see his large erection straining against grey boxer briefs. A small wet spot of pre-cum already had formed on them. Kate unbuttoned Neil’s shirt, exposing his chest and stomach and traced her hand down him to his waistband.
She pulled the elastic downward, revealing the biggest dick she had ever seen in person. It was long, thick and veiny with a big mushroom head, fully engorged, almost throbbing. Neil looked nervous as Kate took it in her hand. He moaned approvingly as she began to stroke it. She smiled at him as she lowered her head toward his big prick. She playfully circled the head with her tongue, licking the pool of pre-cum out of the opening, then letting the whole head slide into her warm mouth.
Neil was pretty inexperienced, having just done some petting on a few dates and had one girl jerk him off. The feel of Kate’s mouth around his cock was unlike anything he experienced before. Kate began bobbing up and down on half the length of Neil’s long, thick rod, stroking it from the base with her other hand. She obviously knew what she was doing, he thought, remembering some of the stories he had heard. Up and down she rhythmically sucked him. It felt incredible and he felt the build up of his load coming on. He watched as she expertly pumped his shaft in rhythm with her lips sliding up and down. Occasionally she was taking more of his length in her mouth. He felt the head of his cock hit the back of her throat. She didn’t gag, but she didn’t take him deeper.
Neil leaned back against the seat, taking in the view of his cute young friend enthusiastically sucking and stroking his rigid pole. He felt himself building to a huge explosion. She seemed to suck him faster, even harder as she sensed his climax. Neil groaned as he felt himself shooting gobs of cum in Kate’s mouth. Rather then pulling off, she sucked downward, letting it all flow into her mouth and down her throat.
Sucking Neil’s big cock made Kate horny for more, she lifted her skirt showing Neil she was bare underneath. Her bush was full, her lips were wet. She wanted to ride that big dick. She moved his hand to her wet mound. He seemed nervous as fingers felt her wetness. “I think I should probably get home,” Neil said unexpectedly. Kate’s heart sunk. “I have to work at my job early tomorrow,” Neil explained, drawing his hand back.
Kate jarred back to reality as her driver pulled into the hotel. She only had half an hour until she was supposed to meet Neil in the bar at the fine steak house in her hotel. She checked in and decided to grab a quick shower. As she washed between her legs, her mind drifted back to that night, Neil’s long thick cock. What would it have felt like had he pulled her onto his seat and let it slide up into her. She slid two fingers into herself, wet at the thought. She finger-fucked herself to orgasm imagining herself riding him.
Kate slipped on a short black dress, a black lace bra and panties underneath. The neckline complemented her ample bust. She fluffed her hair the the mirror, grabbed her clutch and headed downstairs. She peered past the hostess stand to the bar to see if she could get a glimpse of him without him noticing her, but Neil was sitting at the bar looking towards the entrance and she quickly caught his eye. Kate walked towards him as he waived. He stood and greeted her, hugging her close and kissing her cheek, “so great to see you he said.” Neil was tall and had stayed in good shape. The years had been good to him. They sat and Kate ordered a glass of wine.
Over dinner Kate learned that Neil’s marriage had been a long slide downward. They had stayed together for their children and Neil said he would probably just stick it out at this point, but his unhappiness about his wife was nearly as palpable as his excitement to see Kate. The shy boy of prom night had blossomed into a handsome man and a good conversationalist. Kate let her mind wander about what the night could turn out to be. Neil had shared that his wife was out of town for the weekend, so it was apparent to Kate that this could be as much as she wanted it to be. And yet she wondered how she had gotten to this point so quickly.
The weekend with Ann and Rob had unleashed her sexually and yet she felt bad about fantasizing about what it might be like later that night to be riding a third man other than her husband in just under a month. What was going on with her? Why did she want this? The sex was good if not somewhat predictable with Tom. Was it the excitement, the nervousness? The experience of a big hard dick she hadn’t had before?
“You’re daydreaming,” Neil. “Oh, sorry, a little bit of a long day traveling” Kate replied. “Do you want to get a table and order dinner, or . . . ? “Room service?,” blurted Kate. “Or have another glass of wine?” Neil finished his sentence. Kate blushed. “Sorry, I, I . . . .” “It’s ok, room service sounds like a terrific idea,” Neil replied, signaling the bartender for the check. They headed for the elevator. She invited me to her room already, Neil mused to himself. He certainly hoped the night would go this way, but never imagined it moving this quickly. He smiled at Kate, watching the corners of her mouth turn up at she smiled back. Those lips, he ached to see them around his cock again. As the elevator headed upwards he pulled her to him. “It’s so great to see you, Kate. I have thought so much about you through the years.” “You have?” she replied. “What have you thought about?” “Our prom night of course, how good it was, but also want a goof I was for ending the night early. I don’t know why I got so nervous.” Kate moved her face close to Neil’s ear, “are you nervous now?” Kate asked. “No,” Neil smiled, “but I am pretty excited.”
The elevator doors opened and they made the short walk to Kate’s room. “Shall I open some wine,” Neil asked. “How about your zipper?” Kate shot back. “Well I can do that too,” Neil stammered. He fumbled with his belt, pulled it off, unbuttoned his pants and unzipped them. He large cock was already hardening in his boxers, he pulled the elastic over his growing erection. Kate’s eyes widened at the sight of his big cut dick, huge mushroom head, long shaft, big balls handing down below it. So much bigger than Tom and even bigger she thought than either of the other guys she had recently been with. Kate sunk to her knees in front of Neil, took his big cock in her hand and began to stroke it. She looked up at him and smiled. “You have the biggest dick. I have been thinking about it all day.” “I’ve been thinking about you sucking it,” Neil said. Kate circled the head with her tongue, tasting his pre-cum.
Opening her mouth she let the big head slide across her tongue and back into her mouth. “Mmmm,” Neil moaned, “that is so good.” Bobbing on his cock, Kate slid Neil’s pants down and he stepped out of them as he took off his shirt. Neil gently put his hand on the back of Kate’s head and slid his cock deeper into her warm mouth. “Mmmm, yes, suck it. It feels so good.” Up and down she bobbed on his hard cock. Neil moved his hips along with her, getting her to take as much as she could.
He felt himself building, “let me take your clothes off Kate.” Kate stood up and Neil slipped her dress up over her head. Wanting to get back to sucking him, Kate quickly slipped off her bra and slid off her panties. Not long ago she would have been self conscious being naked in front of someone new, but seeing the pleasure others took in her body recently gave her confidence and she longed to have Neil see her. Neil had remembered her body from that prom night when she pulled up her skirt—her firm flat stomach, round perky breasts, and triangle of thick brown pubic hair.
Now curvy, with much larger breasts with long hard nipples—the longest he could remember seeing, Kate still had a nice hairy pussy, puffy with prominent lips. He led Kate to the bed and guided her to lie on her back with her head on one of the pillows. He climbed on top, straddling her stomach, his big cock sticking straight up. Neil grabbed Kate’s nipples and pulled on them firmly, then leaned down and sucked them one at a time.
He licked down between her tits, making them wet before squeezing them around the shaft of his cock. He had only seen this in porn, his own wife being pretty flat chested. It was as good as he imagined. He fucked Kate’s tits, thrusting forward until the end of his cock reached her open mouth. As his orgasm began to build he rose up, straddling her breasts and thrust his cock in and out of her mouth. She felt the head hitting the back of her throat.
“Oh, Kate, suck that dick, baby, I want to cum in your mouth.” Kate grabbed his shaft and pumped it as she sucked up and down on the top half of his huge erection. Neil felt himself explode in her mouth. “Ohhhhh, yesss,” he moaned as he shot ribbons of cum into Kate’s mouth. She kept sucking him until he had emptied himself in her. “That was incredible, Kate.” I have never had head like you give.
Still erect, Neil couldn’t wait to explore Kate’s body. He always thought about what would have happened that prom night had he not gotten cold feet. He had stroked his cock so many times imaging eating and fucking her. Now he was about to. He kissed down her neck to her breasts, taking a long, hard nipple in his mouth. He sucked it hard and then bit it playfully before moving to the other one. His hand slid down her stomach to her wet mound. She was so wet. Two of his big fingers slid in easily. All he could think about was burying his huge cock in her, but he fingered her rhythmically while kissing down her stomach to the top of her bush.
He finger-fucked her harder as his tongue found her clit. He pulled his fingers out and replaced them with his tongue. Pressing his face to her, tasting her juices, parting her prominent labia with his tongue, her soft bush against his face. Kate moaned softly as he ate her pussy. As she enjoyed his tongue her mind turned to his huge cock and how much she wanted to feel it inside her.
She moved her hips and guided him off of her onto his back. “I want to ride that big dick,” she told him. Neil smiled as she straddled him, feeling the head at her opening. They both had thought about this moment, Kate moaned as she impaled herself on his entire length. Neil’s wife always complained about sex, including complaints about his size. Kate easily took every inch. “You’re so big, I love it,” Kate said as she glided up the length of his shaft and then quickly back down. Neil reached up, pulling on her hard nipples, watching her ride him, loving the sight of his entire dick disappearing in her brown bush. “You feel amazing,” Neil responded, “I have thought about this a lot.” “You have? Tell me what you have thought?” asked Kate. “I’ve replayed our prom date in my mind many times, but it always ends with me fucking you, cumming in you over and over again.”
“Fuck me now. I want your cum,” Kate replied.
Neil rolled Kate over and plunged deep inside her. “Oh yes, that feels so good,” said Kate, “fuck me deep.” Neil rose up on his powerful arms and thrust his hips against her, every inch of him stabbing in and out of her. The rhythm of his pubic bone against her clit, the head of his long cock finding spots in her deepest depths, Kate felt herself building to an orgasm. She didn’t cum from penetration often, but Neil was equipped to make that happen.
As his dick again plunged deeply, she started to cum, a deep, toe curling orgasm, her cunt tightening around him even more. He continued to fuck her as she shuddered to a finish. He rolled her over to all fours, loving the sight of her round ass. He grabbed her hips and again thrust his erect dick all the way in her. Hard and fast were his thrusts. So deep, so good. He felt even deeper now. He thought about cumming in Kate’s pussy so many times and now he was going to do it. In and out he thrust, hard, fast, deep.
His climax built, his thrusts now each ending with shots deep inside her. He pulled out and rolled her over, moving up to straddle her chest. His cock was dripping with the last of his cum which he rubbed against her lips. She opened them, taking the last of his cum in her mouth and swallowing it. His moved his cock against her face, getting her to lick him off.
“Stroke me and lick my balls.” Kate complied. She took his half engorged cock in her hand and opened her mouth to accept his scrotum. Licking his big balls, she stroked his long shaft. It didn’t take long for him to rebound. Kate’s mouth and hand soon had him rock hard again. Neil moved around so his cock was above Kate’s face and lowered himself so the engorged head of his penis found her warm mouth. Taking a big cock in this position intimidated Kate. Seeing that long shaft, his big balls handing down, she felt at his mercy. She felt his face find her pussy.
His tongue slid up and down her still-wet slit as he slid more of his hardness into her mouth. He moved his hips, sliding the head and serveral inches in and out of her mouth. Kate never loved 69. She found it too distracting, but she was so turned on by the sex she was having with Neil that she willingly sucked him while enjoying how he stimulated her. Neil’s slow thrusts grew longer and more of his cock filled her mouth. She felt the big head push into her throat. She tried to relax and not gag on him, but she was used to being able to take Tom’s entire length. She wondered it even half of Neil was in and hoped he didn’t plan to trying to fit more.
Neil pressed his face in Kate’s mound, licking her wet folds as he gently pumped himself in and out of her mouth. He loved the feeling of her lips around him, the feel of his cock gliding along the roof of her mouth until he felt the head fill the back of her throat. He wanted to try to make her deep throat him, but he knew that was an unlikely feat. Even still, he pushed the limit, pressing ever so slightly forward as his dick bottomed out. To his surprise Kate didn’t gag.
With the next thrust he stopped when his length had hit its max and held there. Kate gulped and Neill pushed forward. Kate felt the head press past where it had been, further into her throat. Neil gently leaned back, keeping his cock where it was but letting it more in line with the angle of Kate’s throat. He looked down to see her lips about 3/4 of the way down his nearly 10 inch shaft, and the bulge of his head, prominent in her throat. He rocked gently, allowing maybe an inch of him to draw out and then pushed back in. “Oh take it deep baby,” he said as he pushed it forward.
Kate breathed through her nose as she felt his balls brush just above the bridge of her nose. He drew back more this time, and then thrust forward a little more forcefully. Kate’s relaxed throat accepted him, all but about two inches. But it was so much that Kate stopped him on the next thrust. He pulled it out and she gasped for air. “It’s so much. A little too much. I love sucking you, but you’re so big. Lay back and let me do it this way.”
She guided him to his back, his huge dick sticking straight up. One all fours at his side, her ass not far from his chest, she started sucking his cock again. His fingers found her wet hole as he watched her blow him. She gave the best head he had ever had. She pumped the base of his shaft and sucked up and down on him, taking him as deep as she could before bobbing back up. He pumped four fingers in and out of her dripping snatch as she stroked him into her willing mouth. He was about to come again, and he reached for the back of her head, pushing her down on his length, at least half of his big cock in her mouth as it exploded. He held her there as he emptied himself in her mouth. Kate swallowed every drop of his hot load, then looked at him and smiled. “You like to cum in my mouth,” she asked. “You’re incredible,” he said.
Kate laid on the bed next to Neil, her arm draped over him. Her warm, wet mound pressed against his leg, her breasts, against his side, he could fell her long right nipples against him. She gazed down at his now flaccid cock, still impressively long against his stomach. It had certainly been worth the trip. “Do you ever wish you could go back?” Kate mused.
Neil responded, “to high school?, well maybe just for a night, or a summer.” “Yeah, if you had fucked me that night, you could have fucked me all summer,” Kate laughed. “Don’t rub it in, I regret it enough,” said Neil. “Well we can make up for some of it, I guess,” Kate responded, reaching down and taking his dick in her hand. “Not worn out are you,” she joked, his cock clearly showing otherwise as it hardened. “Not a chance,” he said. He rose up and pulled Kate towards the side edge to the bed. Neil stood and spread her legs, pulling her down so her ass was at the edge of the bed. He put the head of his cock at her opening and thrust himself balls deep into her pussy.
Watching her lips spread wide around his shaft as he thrust in and out of her, Neil reached down and rubbed her clit. Kate moaned in ecstasy as he pounded in and out of her. Neil watched Kate’s tits bounce with each thrust. Having cum several times already he knew he could last a long time. He pulled Kate by the hand up off the bed, turning her around facing away from him. He grabbed her hips, slid quickly back inside her, thrusting his pelvis against her ass, forcing her forward onto the bed. Her round ass sticking up in the air, Neil continued to fuck her wet hole, his balls slapping against her with each stroke. As Neil kept fucking her, Kate felt herself again build to orgasm. As his long cock filled her, her pussy began clenching around him as she came, moaning his name,
“yessss, fuck me Neil, fuck me.” “Ride me and let me suck those nipples,” Neil commanded. They moved onto the bed and Kate again mounted his hard cock, riding up and down as he alternated sucking her long, hard nipples. How long can he go, Kate wondered, as she slid up and down on his cock. Fifteen minutes later, she continued to ride and realized she may cum again before he did. She glided up and down his rock-hard shaft feeling her climax rise again inside her. “Ohhhh,” she moaned, “I’m going to cum again.” Neil thrust his hips upward as her pussy tightened and she came.
“Get on your knees and finish me,” Neil directed. Kate slid off the bed and knelt beside it, her back against it. Neil moved in front of her, grabbed the top of her head and forced her onto this engorged member. He began fucking her mouth again, “suck it baby, you know you want to swallow more cum. You love cum don’t you.” Kate moaned in approval, taking his big cock in and out of her mouth. He pushed forward, plunging deeply and this time, the suddenness caused her to gag, saliva running out of her mouth and her eyes watering. “You like trying to swallow my big dick don’t you?” Back he plunged, again sticking his dick into her throat, causing her to gag again. “Lick my balls again,” he ordered. She licked down his shaft to his big hairy balls and sucked one into her mouth. Neil jerked his own dick this time while she licked him. “Oh yeah, baby, lick those big balls.” As he neared orgasm, Neil moved the head of his cock back between Kate’s lips and began thrusting in and out of her mouth. “Drink my cum, baby,” he ordered as his balls began emptying again, streams of hot cum coursing across her tongue and into her throat with his thrusts. Neil’s wife had not blown him in years. Tonight Kate had sucked him off three times.
Kate and Neil laid down on the bed, her head on his chest near him and drifted off to sleep. Neil awoke to the sound of the shower. He slipped in, brushed his teeth and then joined her. He washed her body, and she washed his. His fingers explored her pussy which was very wet again. He bent her over against the tiled wall and thrust his dick deep inside her. He pumped in and out of her while she moaned softly. He watched her tits swing back and forth with his forceful thrusts, and enjoyed the view of her round white ass being bisected by his long hard shaft, the lips of her pussy enveloping it as he disappeared inside her.
Watching himself pump his cock inside his married, old friend was too much to take and he soon was shooting his load deep inside her. He found her clit with his fingers and rubbed it until she came, his dick still inside. He felt her muscles contract around him as she came in waves. They kissed, dressed and then had to bid their goodbyes. Perhaps until another time, they both mused silently, perhaps hopeful, but leaving the sentiment unspoken.
