When Jesse finally arrived at Grandma's he was tired ... damn tired. He had been riding in the car in the summer heat all the way to the coast, then on a ferry, then on ANOTHER ferry, and then he finally arrived at Grandma's manufactured house on some crappy dumb island he didn't even remember the name of, it's that boring.
While his Mom and Dad caught up with his Grandma and Grandpa in the living room, he took his suitcase to his usual bedroom, only to find the bed unmade and girl clothes all over the place.
"Grandma!" he yelled. "Who's been in my room?!"
Grandma walked up. "I'm sorry, Jesse, but Kristen is visiting too, and she's been staying in here for a week now." She then steered him toward the other guest bedroom.
Jesse immediately stopped walking. "Grandmaa! I always stay in this room!"
Well, all but the first year he had stayed with Grandma and Grandpa, anyway, he thought to himself. For old people, they sure had a lot of sex, and since the other guest room was right next to their bedroom ... ugh. He was NOT sleeping in that other room again!
"My allergies..." he whined. That was the excuse he had used after that first night listening to them go at it.
It worked again. "All right, Jesse," Grandma sighed, "I'll ask Kristen to move her things when she gets back from the beach."
Jesse dropped his stuff off in the corner of HIS bedroom and chatted with his parents and grandparents in the living room while they waited. Jesse's Mom and Dad were just getting up to leave when the front door opened and in walked a vision of loveliness.
The girl was a little shorter than Jesse, in cut-off shorts that revealed shapely, long, luscious legs tapering down to dainty feet in flip-flops. Up from the shorts a slim midriff showed below a bikini top that covered small but nicely formed breasts. A small, cute nose under sunglasses was framed by blond curls spilling from her head to her shoulders. Her skin was bronzed from the sun.
As she turned and removed her sunglasses Jesse gaped. "Kristen?" he asked. The last time he had seen his cousin had been years ago, when she was just a little girl and he the same age.
"Jesse?" She smiled and came forward to give him a big hug. "It's so good to see you!"
Jesse was aware of Kristen's bikini-covered boobs pressing against his chest so he didn't immediately break the hug. She did after a couple seconds, not seeming to have noticed his teenage lechery. Then she saw his parents.
"Auntie Barb! Uncle Jack!" More hugs. Jesse's parents excused themselves shortly thereafter, as they had to get back to the main island to catch their cruise ship. Yes, they were abandoning Jesse with the grandparents while they went on a #&$%ing cruise!
Of course, Jesse wasn't complaining as much about that anymore.
After Jesse's parents drove off, Grandma told Kristen of the boy's allergies and she grudgingly gave up the room. She gave Jesse an annoyed look as she went so he followed in order to help move her stuff.
Jesse started to help gather up her clothes, and then stopped when he realized he was holding her thong underwear.
She sighed with exasperation and grabbed it from him. "Out!" she yelled.
Dinner was a quiet affair. Jesse's Grandma was not a very good cook, but his Grandpa had always said that wasn't why he married her. Ugh again, Jesse thought.
Jesse kept stealing glances at Kristen, now in a tight t-shirt. He could still make out the swell of her growing teenage boobies. She caught him looking once and gave him a dirty look. 'Maybe this isn't going to be as good a couple weeks as I thought, ' he thought.
Jesse was pretty tired from the trip, so went to bed early. He didn't even have enough energy to whack off. Well, he tried, but fell asleep partway through. For a 15-year-old guy that's pretty damn tired.
Jesse was having a nice sex dream where he was spooning with Tammy, a cute girl from school, his hard cock pushing into her pussy from behind, when he suddenly woke up. He immediately noticed three things:
1. It was dark.
2. There was someone in his bed!
3. He couldn't move!
As for #3, Jesse had a condition where sometimes when he woke up he experienced sleep paralysis, which is a momentary state where your body doesn't switch off the natural immobility that occurs when you dream. Sometimes it went away after a few seconds or minutes ... it was hard for him to tell because it always seemed like an eternity!
#2 was his main focus, though. He calmed himself and took stock of what he knew after a few seconds:
A. He was the big spoon in this position. He could feel someone's warm back through a thin layer of fabric pressed against his front.
B. There was curly hair in his face. Kristen?
C. The head of his hard cock was wedged somewhere tight, and very warm!
For some reason Kristen had slipped into his bed and snuggled up against him. His dreaming mind had translated the physical sensations his sleeping body was experiencing into the form of a sexy dream, and his cock had hardened accordingly.
Jesse wondered if his cock was actually inside Kristen's pussy. He still couldn't move, but he could feel his penis throb a little at the thought.
Kristen made a little "Mmn" sound as she felt that. Was she awake? Why had she done this? Jesse couldn't figure it out.
Jesse's cock quickly became rock hard as he continued to think that it might be in his sexy cousin's vagina. It started to throb. Kristen's breathing became heavier as the sensations from his pulsing cock stimulated her vagina.
Finally, Jesse felt strength return to his limbs. He was torn between pushing his cock deeper into the sexy, seemingly sleeping girl, and pulling out to find out why she had done this. It was difficult, possibly the hardest thing he'd ever had to do, but he slowly pulled his hips back, little by little, extricating his cock from between Kristen's butt cheeks.
She moaned with disappointment. Jesse shook her shoulder. "Kristen?"
"Mm?" she grunted. She didn't seem to be awake, or at least not fully.
A feeling of deja vu came over Jesse. A memory flashed into his head of an 8-year-old Kristen sleepwalking when Jesse's family had visited hers years ago, walking around like a zombie. What had her parents done then?
He remembered. "Kristen," he said softly, "go to the bathroom." Her parents had told her to do this when she sleepwalked. Once she peed she would just go back to bed and stay there.
Kristen pushed herself out of bed and through the door. Jesse grabbed his robe from the back of the door as he followed the sleepwalking girl.
Kristen walked down the hall to the bathroom, stumbling in and heading to the toilet. In the dim light from the bathroom nightlight Jesse could see that she was wearing a long t-shirt that must have ridden up when she snuggled her butt up to him in bed. She raised the t-shirt to sit and he caught a flash of blond pussy hair. Her eyes were half lidded, not registering that he was there, watching her.
When she had finished peeing she dried herself with some toilet paper, left the toilet unflushed and washed her hands. Jesse's grandparents got their water from a well, so his Grandpa had always told them, "If it's yellow, let it mellow. If it's brown, then flush it down."
Jesse realized that the sleepwalking Kristen definitely knew she was in her grandparents' house. Why had she ended up in his room?
'Duh, ' he thought to himself. 'Because for the last week my room had been HER room.' She had gone in there by habit while sleepwalking!
As Kristen left the bathroom she started to head back to his room. Jesse quickly steered her by the shoulder back to her room with soft words. Grandma and Grandpa would KILL him if they found her in his room in the morning!
Jesse made sure Kristen got under the covers (stealing a peek at her gorgeous legs when her t-shirt rode up as she got into bed), and then headed back to his room.
His cock had flagged a bit, but once he got back into bed the thought that his cock might have actually been in his sexy cousin's snatch brought it right back to steely hardness. It only took a few seconds of rubbing before he shot his cum high in the air, splashing back down onto his stomach. He cleaned himself up.
As he drifted off to a happy, post-orgasmic sleep state he mentally kicked himself. Did it count as losing his virginity when his cock went into Kristen's pussy a little while he had been sleeping? DID it go into her pussy? He wasn't even sure. All he knew was that he had definitely lost his chance to lose his cherry by being a nice guy! Sleep overtook him.
The next morning Kristen seemed to be in even more of a mood than the previous day. She went off on her bike to the beach again, alone, leaving him to explore the nearby woods by himself. It was about 1 PM by the time he got back for lunch, and Kristen still hadn't returned.
Jesse's Grandpa taught him how to play Cribbage. It was difficult but he actually won once. His Grandpa skunked him twice, though.
Kristen got back in time for dinner. She again wore her tight t-shirt, and Jesse kept stealing glances at her boobs. This time she didn't catch him. She seemed to be in a better mood now, her skin a little darker after all day suntanning.
After dinner they played 4-player Cribbage. Grandma and Kristen lost the first game to Grandpa and Jesse, but won the next. The tie breaker was a nail biter, but the ladies won again. Kristen had actually laughed at a couple of Jesse's jokes so it seemed to him like they were good again.
Jesse, of course, masturbated that night when he went to bed. He thought about Kristen's tanned and toned body, her butt pressed back at him as he sawed his cock into her pussy from behind. It didn't take much effort for him to blow his load on his stomach again, with the previous night's experience still fresh in his mind.
Grandpa was horny again. Seeing Kristen's hot teenage body parading around in a bikini and tight t-shirt was quite the aphrodisiac for him. As they had done each night since she had arrived, Grandpa fucked his wife once they were sure the kids had fallen asleep.
Grandpa's grunts and Grandma's moans sounded against their bedroom walls. In the next room, Kristen's mind was dreaming as she heard them. The sex sounds burrowed into her subconscious, turning her mind and body on. As her grandparents reached their sexual crescendo, the sexy noises activated enough of her mind to bring her to a mental level between dream and consciousness.
Bed feels wrong. Go to bed.
Kristen got up, left her bedroom, and headed to what her mind was telling her was her room. She entered Jesse's bedroom, closing the door behind her, and then slipped into the bed.
Jesse snoozed softly beside her, not noticing the intrusion.
After a few minutes Kristen felt cold. Jesse didn't use as many covers as she did. Her hands quested for something warm, finding Jesse's body facing her. He still hadn't noticed she was there.
As she had done the previous night, she turned her back to him and sidled her body back until they were in a spoon position, her movements causing her t-shirt to ride up so her bare bum pressed back against his naked lap.
Warm, good, she thought. Her pussy was still wet from the sexy sounds she had heard earlier.
Jesse woke up. He found Kristen in his bed again, her back pressed against his chest. Also again, his cock had hardened and pushed up between her legs.
'I'm dreaming, ' he thought to himself, muzzily. 'This couldn't actually be happening again.' He figured he might as well enjoy the dream, and pushed his hips forward, making his penis go deeper between Kristen's legs. As he did so the top of his cock shaft slid along her pussy lips and the head of his penis bumped her clitoris. He wasn't in her pussy but it felt good for both of them.
Kristen's breathing sped up as her labia and clit were stimulated by the movement.
Jesse pulled back a bit and did the same again. It felt incredible. He thought he was having a nice sexy dream, and soon it would be a wet dream. He sped up his hip movements.
Kristen's overheated pussy was getting closer to orgasm. She started to roll her hips, her body trying to get the pleasurable object stimulating her pussy lips to go inside, where her body naturally knew it would feel the best.
After a few minutes of awkward thrusting Jesse could take no more. He sped up, and then grunted as his cock started spewing cum between Kristen's legs. He pulled back, shot a spurt of semen along Kristen's outer pussy lips, and then pushed forward, spurting again as the head of his cock scraped along Kristen's inner pussy lips. A small amount of his cum slipped inside the sleeping girl's vagina, and then the head of Jesse's cock bounced off of her clitoris again, coating the area around it with more cum.
Now that Jesse had cum he realized that he was not, in fact, dreaming. Horrified, he pulled back, his cock easily extricating itself due to the extra lubrication he had put between Kristen's legs.
'Oh God, ' he thought to himself, 'what do I do?'
He calmed himself down. Kristen was still sleeping. Could he just do the same thing as the previous night?
Scared, shaking, he touched her shoulder. "Kristen, go to the bathroom."
As before, she got out of bed and headed to the bathroom, as instructed. Jesse followed again, slipping on his robe as he went.
This time he followed her right to the toilet. He could see the glistening of his cum running down her legs in the dim light. He was pretty sure he hadn't put his penis inside her, as it hadn't felt as tight and warm as the previous night. Still pretty damn good, though. There was no chance, then, he thought, of getting her pregnant.
Kristen pulled up her t-shirt and sat down to pee. As she did Jesse grabbed some toilet paper and started to wipe the semen that had dripped down her legs. He kept glancing at her face to make sure she wasn't going to wake up because of what he was doing.
When Kristen was done peeing he handed her some toilet paper. "Clean up all the mess, Kristen," he said. He hoped this wasn't too out of the ordinary so she wouldn't recall any of it. She wiped and wiped and he kept handing her more toilet paper until she had wiped up all of his cum. Then she got up, washed her hands, and then headed back to his room. Again, he had to steer her back to her assigned bedroom.
As he went back to sleep he hoped she wouldn't remember any of that. She would absolutely kill him if she did.
The next morning the grandparents took them to the main island for some sightseeing. Kristen started the day in a bad mood but Grandma turned it around when she let Kristen buy a new tight t-shirt. Neither kid saw Grandpa goose Grandma's butt after the purchase.
Kristen was really fucking horny when she went to bed that night. She didn't feel comfortable about masturbating with her grandparents on the other side of the wall, though, so she fell asleep unsatisfied.
A little later the sex sounds from her grandparents' room started up again, filling her sleeping mind with sexy images and feelings as it had the previous two nights. She rotated her hips, trying to find anything to rub against. Finally, frustrated, her mind once again switched itself to the sleepwalking level.
Bed feels wrong. Horny. Go to bed. Horny!
This time Jesse was awake and ready when Kristen slipped into bed with him. If she was going to keep doing this and not remember, he was going to take advantage of that and finally lose his virginity, he had decided.
He certainly hadn't expected sex on this trip, so had no condoms with him. He would pull out before cumming, though, he assured himself.
He made sure to remain facing toward Kristen's sleeping form, and then waited. Sure enough, within a few minutes her hands quested for his warm body, then, finding him, she turned around and scooted back until her back was against his chest and her butt spooning with his lap again. Jesse adjusted his already hard cock so it slipped between her legs as she settled herself.
Jesse waited a minute or so until Kristen's breathing had become regular. He then slipped himself lower and gently pushed her knees up closer to her chest. It took a few tries but when his cock head started to push into her wet pussy lips from behind he knew he had succeeded.