Jeff Greegan's First Time

Jeff Greegan was driving down the I40 just outside Little Rock. The eighteen-year-old had been given the car by his parents for his birthday, it's not as new or as expensive as some of the cars his friends are driving, but in his mind it's a classic, and really cool. His mobile rang, looking at the caller ID he answered.

"Hey dad" he said.

"Hi son, I was just wondering are you nearly there yet?" said his father.

"Yeah, I'm on the 40 and should be there in a few minutes" replied Jeff.

"Good, remember, when you get your room just text the room number, and enjoy the final part of your birthday present." Said his dad, before hanging up.

A few minutes later Jeff turned in to the motel, parked his car and walked into the reception. "Hi, can I get a room?" he asked the woman behind the counter, recalling the story he had made up, as to why he wanted a room and the false address he was going to use if he was asked for any details.

The woman looked up, she smiled, "Are you paying by cash or card?" she asked, apparently not requiring any of the information he had imagined she would need.

Tentatively he handed over the credit card his father had given him, and moments later the woman, looked up from her computer, handing back his card, she said, "Room 29, on the second floor." She pointed in the direction of the stairs, before returning to the soap she had been watching on the TV.

As he walked towards the stairs, Jeff pulled out his phone, and as he had been instructed, and texted the room number.

A few minutes away, a pretty blonde forty-year-old, sitting in the back of an Uber, looked at her phone, noting the number she received in the text message. She took a small mirror from her purse, giving a final check to her hair and make-up, a quick dab of lipstick, and she returned everything back to her purse. She was feeling a little nervous, this was her first time doing this, not half as nervous as the young guy she was meeting, she knew he was a virgin, but she wanted to give him a day he would remember for ever.

Her car pulled into the motel, she thanked the driver, and walked into the motel. She bypassed the woman behind the reception desk, walking confidently towards the staircase. She easily found room number 29 and knocked on the door.

"Come in", the voice sounded nervous.

She walked through the door, Jeff was sitting on the edge of the bed, a slight look of fear on his face as she entered.

"Hi M...." began Jeff.

She put her finger to her lips to silence him before he could finish his sentence. "Call me Jennifer, or Jenny if you like" she instructed him.

Jeff nodded, and she approached the bed, placing her purse on the small table beside the bed.

"This is your first time then, Jeff"? she asked him. He nodded again. "Then try to relax and we'll go really slowly, and hopefully you will take away some really good memories and a little experience for the future".

She sat on the bed beside him, she could feel him shaking with nerves. "Why don't we start with some kissing, and we will see where we go from there?" she suggested. She turned her head towards him, pursing her lips, his meeting hers halfway. Slowly their kiss progressed from, bare touches of their lips, to full French kissing when he finally built up the confidence to use his tongue. He was quite a good kisser she thought, despite his inexperience, and limited female companionship. As they kissed, his nervousness became obvious again, his hands were clamped down at his side, as if not sure what or where he was allowed to touch. Finally, after several minutes of kissing she felt his hand touch her knee, just below the hem of her dress, but on her knee his hand froze, as if restricted in movement.

She pulled away from their kiss, realising she would have to drive everything they would do. "How about you help me undress?" she asked, slowly standing up, turning her back to him, while looking over her shoulders, a glint in her blue eyes and a slight grin on her lips.

He stood up, his fingers shaking as he took hold of the zipper on her dress, nervously pulling it down. With the zipper open her dress fell to the floor. She stepped away from him, wearing only her bra and panties, she had debated with herself over what to wear, going through drawers of lingerie, but her decision to go simple didn't appear to disappoint him. Hs eyes were on stalks, as he looked her up and down, taking in every inch of her body. She unhooked her bra, her firm heavy breasts being welcomed by a gasp from jeff. As she pulled her breasts free, she noticed her own nipples were even beginning to show the first signs of arousal. Next, she hooked her fingers into her panties, pulling her thong down, wriggling it past her thighs.

Jennifer climbed onto the bed, Jeff still standing like a statue, watching every move her naked body made. She patted the bed beside her for him to join her, he did as she requested. With him alongside Jenny, they started kissing again, but this time she felt his hand brush against her, her side at first, slowly and tentatively moving upwards, nearly tickling her his touch was so gentle. But when his hand glanced off the side of her breast she was happy he was beginning to relax, beginning to explore and starting to enjoy himself.

Jeff had been feeling very nervous, not really sure about what he should or could do. What was appropriate and how forward was he allowed to be. His total lack of experience was leaving him confused. Any previous interactions with girls had got him no further than second base, but Jenny's nakedness was his cue to hopefully fulfil his dreams. He had listened to his friends that had lost their virginity and they seemed to possess a confidence he was yet to earn, his best friend Steve had lost his virginity about nine months ago, his parents were away and he had invited some of his school friends over to the house, at one point in the evening he had disappeared upstairs with Becky Letour, Jeff had followed them and standing outside the door listened to the sounds of them having sex, since then Steve always seemed to have a girlfriend in waiting while Jeff couldn't even get one date. Jeff often heard his sister talking with her friends and by the conversations he had realised that girls are more attracted to boys with experience, their ability in bed often being judged and definitely discussed, but even the lowest scorers on the girls scales were way ahead of guys like him.

Jeff's hand had reached Jenny's breast, the heavy weight and surprising softness of her flesh was not what he had expected, and the feeling of her areola poking out like small lumps as his thumb rubbed the tip of her breast was a very positive signal to him, he was obviously doing something right. Jeff broke their kiss, slowly moving down to her neck, kissing her soft skin, down to her shoulder blades and to her chest. He kissed her breast before taking her nipple between his lips, as he sucked her sensitive nubs they began to grow, getting harder as he flicked his tongue across her nipple. Jenny's chest was rising and lowering as her breathing seemed to get deeper, her hand caressing his back, acknowledging her willingness for him to continue.

"Why don't you get undressed Jeff"? Jenny asked. She had noticed that despite being fully clothed his obvious erection was fully visible as it attempted to break free from his pants.

He looked up to her, blushing, his first time to get undressed in front of a woman in such circumstances, but quickly began pulling at his clothes to remove them. As his cock became free, Jenny felt a sense of relief for the young guy, his cock even though he was still young appeared at least slightly bigger than the nations average size, in her opinion. It had been one issue on Jeff's mind, was he big enough, he had seen some of his friends undressed in the locker rooms in school but had never seen a real erection to compare his to, in the full knowledge that porn dicks were probably much bigger than normal guys. But he had noticed a slight grin from Jenny when he first revealed it, even a nod of approval from her which helped him to relax.

Jenny slid down the bed on to her back, spreading her legs to give Jeff a better view and access if he wanted. She didn't speak, but again he took his cue to his next step. He moved between her legs, his eyes drinking in the sight of her thighs and her pussy. She reached down, using two fingers she parted her outer pussy lips, revealing the depths of her pussy to him. It was at this moment that Jeff realised why he had heard pussies referred to as flowers, as Jenny's fingers spread the inner petals appeared revealing the contained inner secrets. He moved closer, her scent filling his nostrils, the light pink colour of her pussy, the glistening droplets of her natural lubricants, all light years ahead of the grainy porn movies he had been able to procure.

He leaned forward, kissing her inner thigh, she rested a hand on his head. He kissed her again, looking up searching for some guidance. Her hand guided his head towards her pussy, where he kissed her once more. His kiss lingered on her pussy, her hand scratching his head, his tongue flicked against her pussy, his first taste of her inner nectar reaching his taste buds. He continued licking and tonguing her pussy, soaking his own face and her inner thighs with the juices he was extracting. He heard her moan a couple of times, moans that he had only previously heard in porn films.

"Do you want to fuck me?" Jenny asked.

Jeff didn't need a second invitation, he got up on his knees and positioned himself between her legs. He attempted to enter her without any manual guidance from his hand, so Jenny took hold of his cock and guided him inside. Her pussy seemed to swallow his hard cock, sucking him in like a vacuum cleaner, he groaned, feeling her pussy grip his cock from all directions. He grinned, realising he had just lost his virginity. He lowered himself on to her, his hips beginning to move up and down, fucking her. Jenny knew in reality he wasn't going to last too long, but was enjoying his attempt to pleasure her, his mouth sucking on her nipple as he fucked her.

Jenny was right, he was only inside her for a minute or two, when he felt his balls tighten. "I'm cumming, I'm cumming" he groaned. Jenny clamped her hands down on his bare ass, pulling him deep inside her, preventing him from pulling out, wanting to feel his hot young cum fill her up, rather than some porn learned cum shot. "Ungghh" he grunted as she felt his cock throb, his body shake and his hot cream enter her pussy.

Jeff had finished cumming, but he remained on top of her, his cock still at least semi hard in Jenny's pussy. "Kiss me Jeff" she said.

In order to reach her mouth he had to roll off her, now free from her pussy and his very recent orgasm his cock looked as large as it hand before he had entered her. They kissed for a minute, then Jeff pulled back, "I'm sorry" he said.

"Sorry for what" Jenny asked.

"For not lasting longer, and well, only doing it in one position" he replied.

"Don't apologise" she said, "the important thing is you enjoyed it because I definitely did" her slight exaggeration missed by the young man, "and I'm sure there will be plenty of opportunities to try all the positions you've been dreaming of". Jeff grinned. "You never know, we may even have time to do it again if you want".

They both looked down between his legs, and the erect cock that stood at least horizontal from his midriff. They laughed.

"Looks like you won't be needing much recovery time" said Jenny, "I don't remember giving you any oral, so if you'd like to come nearer, I will see what I can do".

Jeff moved his position so his cock was reachable for her mouth, Jenny began sucking him, tasting her own juices off his shaft. Something she loved to do, was to see how long it took guys to recover from sex by sucking them, and in the case of Jeff, it must be a world record, or the sexual hunger of youth, she thought. While she was sucking him, Jeff tried to re=orientate himself so he could go down on her.

"Do you want me to shower first, before you go back down there" she offered, fully aware of the amount of his cum her pussy still contained.

Jeff didn't even pause to her offer, he was kissing her pussy with as much gusto as he had done previously, uncaring of the contents, just thrilled to be able to eat her.

His recent orgasm would improve his lasting ability, she thought, despite his very quick recovery and immediate erection. Kowing he wanted to try many positions, she decided to take full control. "Roll on to your back" she ordered him. Jeff followed her request, his cock standing upright. Jenny straddled him, his cock entering her as she lowered herself down, his eyes glued to the image of his cock disappearing inside her. She began riding him slowly, rubbing her clit against his body as his length filled her, before rising upwards. Jeff reached up, grabbing her breasts as they swung freely from her chest, squeezing them, pinching her nipples.

Jenny felt so aroused, his cock felt long and thick inside her. She could hear herself moaning, all the time rising towards a potential orgasm. "Do me from behind Jeff, do me doggy style" she begged.

Again they changed position, as she positioned herself on all fours, she heard a loud "wow" from Jeff who was excited with the view of her ass.

"Take your time putting it in" she told him, not wanting him to miss, and definitely not wanting his cock in her ass hole.

Jeff made two or three attempts to enter her, missing each time, nearly hitting her ass hole on one occasion. Jeny had to reach between her legs and guide his cock inside her, herself. His body loudly crashed against hers, his hands holding her hips, she could feel her own ass shake with every thrust he made, and his size was definitely hitting the right spot for her. At the angle they were fucking, his cock occasionally brushed against her G spot, and along with her own hand rubbing her clit, she began to orgasm. Jenny used every bit of energy she possessed to refrain from collapsing on the bed in front of Jeff and holding herself in position. Jeff's grunting signalled his own impending orgasm.

"Do you want to cum inside me again Jeff" Jenny asked, or do you want to cum somewhere else"? Asking the question, she knew, but slightly dreaded the answer.

"On your face" he grunted.

Just as she had dreaded, but in the knowledge that it was every boy's dream place to cum. Jeff pulled out of her, trying to get around so he could cum on her face, but he had already reached the point of no return. Somewhere halfway through changing positions one more time, he began to ejaculate, a long thick spray of cum shooting from the tip of his cock and landing between her arm and her breasts. A second string of cum landed solely on her breasts and a third managed to land on her neck, before her fell on to the bed beside her.

They both took several minutes to recover from their exertions, even Jeff's cock shrivelled back to normal size. "I think I need a shower" said Jenny, climbing off the bed. She went into the bathroom, and as the water started to flow she called in to him, "Care to join me?".

In record time, Jeff was standing beside her in the tight cubicle. They began soaping each other, feeling their bodies, kissing. Jenny took a handful of soap and began rubbing his cock, making him as hard as he had been. She pushed him against the wall, kissing him passionately as she jerked him. Jeff was already moaning. Jenny pulled her hands away, directing the jet of water against his soapy cock. Once she had rinsed him of soap she dropped down to her knees. Jenny took his cock and fed it into her mouth, slowly sucking his length, her tongue exploring every ridge and vein, tantalising every sensitive nerve ending. Her hand cupped his balls, gently squeezing, pulling on his sack. Her age and experience of giving blow jobs was no match to his attempts to not cum. Only minutes into her oral manipulations and the first squirt of his cum hit the back of her throat. Quickly she pulled her head away, aware of what was going to happen, and his second spray of cum hit her cheek, a third landing on her chin.

Jenny slowly stood up, with the gentlemanly help of Jeff, grinning, displaying his cream on her face, and the remnants in her moth that she hadn't yet swallowed. "Are you happy now that you came on my face?" she asked him. Only to be met by a huge grin before he helped her to clean off.

Half an hour later the pair left the room, Jeff fully satisfied and feeling as much like a man as he imagined. They walked down the corridor holding hands, just like any loving couple. A door closed behind them along the corridor, Jeff glanced over his shoulder, even at a momentary glance he recognised his twin sister. "Mom, Jessica and dad?, they're here too?" he asked Jenny.

"Yes Jeff, we wouldn't give one of our children a present like you got today, without doing the same for the other would we. It wouldn't be fair, would it?" answered Jenny to her son, "that's why it took so long after your birthday to arrange this and to be sure you were both ready and happy to participate".

Jeff turned around, letting go of his mom's hand. He ran back down the corridor, half leaping with his arms extended, grabbing his sister and hugging her tightly. Then he looked over to his dad who was holding Jessica's hand, and grinning said, "Thanks for the best birthday present ever dad!"