Awkward

[ladyoffiction]

Reggie smiled as she was led into his bedroom. His apartment was the same basic layout as hers, so she knew exactly where he was going. She was surprised when he completely stripped down in front of her. She was still wearing her pants--her bra and shirt abandoned in the living room. She shrugged at him, trying not to look too put off. "Well, we're not really looking for romance. Just remember it's usually better to undress the girl first. But don't worry, you'll get better with practice."

She kicked off her shoes and slipped her pants off, followed by her red panties. Her pussy was completely waxed, her panties sticky with her juices. She laid down on his bed, spreading her legs. "Remember, you promised to fuck me hard."

 

[JustABadBoy]

"Remember, you promised to fuck me hard," Reggie told him, laying back on his bed, her clothes shed from her beautiful body. Then she spread her legs invitingly.

Greg stepped closer to the end of the bed, looking right down onto her, his gaze set upon her pussy. It was ... simply amazing, and again unexpected. Greg had never once considered Reggie's color, not before today as he attempted to befriend his beautiful neighbor nor tonight as he attempted to lose his virginity to her.

But now, looking at her most private parts, he was simply in awe of her color. Greg had seen photos of pussies, on the internet and in his father's Playboys. But he'd never seen -- or, maybe just never really thought about -- a black girl's pussy. (As he stared at her in awe, he found himself asking, Black? Colored? African-American ...? Are you really having this debate now you dick?)

He moved closer, sitting on the edge of the bed, reaching to caress Reggie's thigh as he simply continued to stare. Her pussy was black and brown and dark brown and pink and ... it was so ... beautiful!

He caressed his hand toward the inside of her thigh, hesitantly, then looked to her face and asked, "Can I touch it?"

 

[ladyoffiction]

Reggie waited patiently as he stared. This was the first pussy he's seen up close and personal, so she would let him look at it, play with it, do whatever he wanted. She smiled up at him a bit, her hands tucked behind her head. He was so cute.

She threw her head back and laughed at his question. Like, really laughed. It took her almost a full minute to regain her composure. Chuckling, she sat up and kissed his cheek. "I'm sorry, baby. I didn't mean to laugh." She cupped his face with her hands, meeting his gaze. "Greg, we're going to have sex. This involves you putting your dick in my pussy. Do you really think I'll mind a few fingers down there?" She chuckled and kissed him. "You're thinking too much. As long as you stay away from my asshole, you're free to do whatever you like." She laid back down on the bed, gesturing for him to touch her.

 

[JustABadBoy]

As soon as he'd asked the question, he knew what her response was going to be, and when she began laughing hysterically and explaining to him the way things were going to be, he couldn't help but laugh with her.

She laid back again, looking at him pleased. He had a definite feeling that she was enjoying having a virgin again -- oh, wait, she'd said he was her first. A night full of firsts.

He hesitated for a moment, then slowly caressed a hand down her thigh to her belly, across her belly to the other leg, up it and back, across her belly again; as he did, his palm passed over the smooth skin where he'd expected to see a patch of kinky, black hair, and then, on the second pass, a bit closer to her pussy.

He knew she'd given him permission -- he knew she was waiting, for him to do something! -- but he was still nervous as hell. Occasionally, his hands would tremble just slightly. Finally, he just told himself, Do it! Touch it!

Moving his hand to above her waxed skin, he slid it down to her pussy and pressed his index finger between the wet, warm lips. It felt unbelievable. I'm touching a woman's pussy! I'm touching Reggie's pussy, oh my fuckin' god!

 

[ladyoffiction]

Reggie waited patiently, letting him take as much time as he needed to build up his courage. She found his hesitation cute. If it had been a more experienced guy, she would have already pushed him down on the bed and had her way with him. She was usually the dominant one when it came to sex. But since Greg was a virgin, she wanted to let him experiment and get used to a woman's body. If that meant Reggie had to be submissive, than so be it.

Finally, his finger slipped passed her lips. She smiled. About time, she thought. Spreading her legs a bit wider, she opened her outer lips with two fingers, letting him get a better view. She took his finger and guided it up to her clit. "This is the clit. Rub it."

 

[JustABadBoy]

Her reaction -- simply to his touching her nipple-sized piece of flesh -- amazed him. He was doing this to her; he was giving her this pleasure.

As he fondled her clit, manipulating it side to side a bit, then up and down, harder and softer, slowly and faster, he watched her face contort, watched her body writhe, until finally he found the one touch that seemed to effect her the most ... and, smiling with pride, persisted.

He knew of orgasms, female orgasms -- he'd heard his slutty sister on the other side of the wall all through his high school years -- but now, right now, he had to see Reggie cum at his touch. He wanted inside her, and she wanted him there, too ... but seeing her like this was worth the wait, he thought.

 

[ladyoffiction]

Once he knew where to touch, he was surprisingly skilled. He was experimenting, yes, but it was driving her crazy. She clutched the pillow as her body twitched and spasm each time his finger hit a particularly sweet spot. Oh, he was quite good at this. She gasped as she reached her climax and let out a long, low moan when she came. She found herself chuckling a bit, looking up at him. "Very very good, baby."

She sat up, wrapping her arms around him and pulling him down so he was laying on top of her. She kissed him. "No more games. I want you to fuck me. Now." She kissed him again, spreading her legs to give him full access.

 

[JustABadBoy]

Watching her orgasm was phenomenal. He'd heard so many stories from his sexually active friends that knowing whether their girl friends had cum or not was sometimes a mystery to them.

But Reggie's climax -- uncontrolled writhing, a loud pleased gasp, and a long, satisfied moan -- had been unmistakable, even to inexperienced Greg. She complimented him, pulled him to her, and told him it was time to fuck. He agreed; his dick was hard and lonely.

He positioned himself and, surprised, immediately found his dick pressing at the wet space between her swollen lips. He pushed, finding tight resistance, but he knew he was doing it right; so, he just pushed harder ... and with a deep, satisfied groan, his dick intruded her warm, wet hole.

 

[ladyoffiction]

Reggie gasped in ecstasy as he slipped inside her, her back arching. She hadn't had sex in so long, she had forgotten how good it felt. Her eyes rolled back as she clutched onto his shoulders, grinning. "God, you feel so good," she managed to mumble. She was having a hard time focusing on words with his dick inside her.

Taking a deep breath, she met his gaze, calming herself enough so she could focus on him. "Ok. No, thrust in and out nice and slow, alright? Don't rush, just take your time. It's ok if you come inside me; I'm on the pill."

 

[JustABadBoy]

Reggie arched below him, clutching at his body. "God, you feel so good."

Greg lowered his weight to his elbows, stationed on either side of her shoulders, lowered his head, and just started fucking, fucking, fucking; the feeling was like nothing he'd ever experienced with his dick in his hand, and the pleasure overwhelmed his ability to consciously consider whether he was doing it right or wrong, whether he was pleasing her or not ... he was simply playing rabbit and hurrying to get off inside of her.

"Ok, no, thrust in and out nice and slow, alright?" she directed him. "Don't rush, just take your time. It's ok if you come inside me; I'm on the pill."

He felt suddenly stupid; not embarrassed, but plain stupid. He'd never even considered protection; he'd simply been anxious to lose his virginity. He stopped his thrusting for a moment, then resumed it, slower, more methodical ... calmer.

He turned his arm in, slipping a hand below her neck and arching it. He pressed his mouth to her neck and kissed her, wet and passionately. He'd seen a guy do it in a movie once and had always thought the move looked romantic. He was concentrating so hard on the passionate work of his lips and tongue upon her neck and collar bone that he hadn't even realized he was no longer thrusting into her.

 

[ladyoffiction]

Greg was a bit sloppy at first, but when he slowed down and focused on his thrusts, it was much better. He was getting the hang of it quickly. When he started to kiss her neck, she thought he was simply drooling on her. She frowned as he stopped thrusting and focused on her neck. "Alright, Greg..." she pushed him at his shoulders, causing him to stop kissing her neck. She rubbed the wet spot, a look of disgust flashing on her face. "You can kiss my neck, but don't use your tongue. It's kind of gross. Kiss it, bite it a little. And you stopped fucking me when you started, so you're going to have to practice multitasking."

Thinking she sounded a bit too harsh, she quickly spoke again. "But it's ok. You're doing very well for a virgin." She kissed him, pulling him down again. "Just focus on fucking me for now." She smiled at him. "I want you to come for me, Greg. Ok?" She grabbed his hips and guided them in a thrusting motion again, moaning to encourage him.

 

[JustABadBoy]

He'd always imagined that intercourse would simply be a matter of sticking it in and moving it about. His experience had him again cursing in silence, You're fucking this up, you're fucking this up!

He abandoned his failed attempt at her next of being sensual and concentrated on fucking her. She felt so unbelievable; tight, wet, warm, and experienced, as she guided him in his movements, making their bodies move as one together.

As the pleasure welled within him and he knew another orgasm -- this one not in his own pants! -- was imminent, he wanted to say something romantic, or erotic, or nasty. He remembered his failed attempt earlier at dirty talk. He kept quiet, and just kept fucking her.

 

[ladyoffiction]

Since he was focusing on the 'fucking' part of the sex, Reggie decided to take the more sensual part of it into her own hands. She ran her hands up and down his arms and chest and back. She continued to moan, her body shivering at each thrust. He was doing very well; at least her body thought so. She kissed him everywhere she could reach--his lips, his jaw, his neck, shoulders, chest. She moaned continuously, letting him know that he was doing well.

The explosion inside her was a bit surprising; she was used to guys telling her they were going to cum. There was something incredibly sexy about making a guy cum, so she loved it when they told her. But Greg had stayed quiet. She moaned loudly as he filled her up, her own orgasm triggered by his juices. "Oh, Greg!" she said loudly, her body shuddering. "Fuck. Fuck...that felt so good."

 

[JustABadBoy]

He exploded with a deep, guttural grunt of satisfaction; his dick pulsed inside of her, again and again, unloading. Physically, it wasn't any different that when he'd creamed his pants earlier; but emotionally, it was pure heaven.

He'd lost his virginity -- and not just to anyone, but to the sexiest woman in the building ... on the block ... in the whole city! She was all over him -- her hands, her lips, her tongue -- doing all to him that he was already hoping to learn to do, to be able to concentrate on while also fucking the next time they did this.

There will be a next time, right? he was already thinking. He was presuming a lot; they were only together because he'd selected the wrong movie -- or right movie, depending upon your point of view -- and then gotten lucky enough to catch her in the right mood. She probably had a boyfriend already; maybe two or three! She was that beautiful, he already knew; and she was erotically sensual, which he knew now.

He wanted to fuck her again and again and again in the days and weeks and months to come. But ... for now, as his weight simply fell upon her, he just wanted to enjoy the aftermath of yet another orgasm ... and rest for a moment.

 

[ladyoffiction]

Reggie grunted a bit as he collapsed on her, most of his body weight landing directly on her. She chuckled a bit and pushed him by his shoulder, rolling him off of her. She turned her body so she was facing him, pulling away enough so he was no longer in her. She smiled at him, stroking his face. "That was very good for your first time, Greg. Very good. There are still some things that you need to work on, but with practice you'll get it."

She leaned in and kissed him before snuggling into his chest. So, where did they go from there? It wasn't as if they had any romantic encounters before this, they had just hung out a few times and now she was naked in his bed after an intense orgasm. She propped her head up with her hand and studied him for a moment.

Gasping, she sat up and grabbed her pants, pulling her phone out of the pocket. Swearing, she stood and grabbed her underwear, slipping them on. "I'm going to be late for work!" She let off a string of swear words under her breath as she slipped on her pants and then her shoes. "Umm..." she looked at Greg and smiled. "I'd love to do this again. I'm free tomorrow after six, if you want me to stop by?"

 

[JustABadBoy]

"I'd love to do this again," she told him, heading out of the bedroom. "I'm free tomorrow after six, if you want me to stop by?"

And ... she was gone.

Greg just laid there, naked, his semi-erect dick pointing toward her escape, thinking, What...?

He'd heard all of the bad jokes about guys finishing, particularly with one-night stands, and heading out the door, leaving their lovers alone, and often pissed. But he'd never heard of it happening to the guy.

He laid there for a long moment, grasping his sticky dick and massaging it gently. It was becoming sore; he hadn't known that such a virginal work out could do that to a man, and he couldn't have realized now that tomorrow morning, his gonads would feel like someone had kicked him in them.

He finally accepted that she'd had to leave, and set about getting ready to end his evening. He made his way around the apartment, turning out lights and checking that the front door was locked. He couldn't help but be more aware than usual of his big dick dangling before him as he padded around the rooms. Nice job, big boy, he thought, laughing. You finally did some damage... made a name for yourself.

Greg was tickled that Reggie had enjoyed herself with him. He'd had these horrible fantasies about his first time, and instead of having to walk around with his head in shame the next morning, he was ready to walk onto campus tomorrow with his head held high.

Oh, crap! he thought. How do I brag about losing my virginity to a college girl ... without admitting that I was still a virgin...? As he finished up his bed time chores, he decided that he wouldn't brag, per se; he'd just let his smile and unspoken pride give clues and begin conversations. Greg was confident that by the end of the next school day, all of his friends would know he'd gotten laid by the most beautiful woman he knew.



The next morning, after groaning repeatedly at the severe wear and tear he was feeling down there, Greg headed out the door, a huge smile on his face as he recalled -- for yet the umpteen thousandth time -- the performance of the previous night.

He was heading out of the building when he caught sight of Reggie outside the Manager's office, a high cupboard door blocking his view of her face. He stopped and ogled her long legs and tight ass as she was trying to get a file or something down from a shelf. I tapped that, he thought, then immediately blushed at the thought of saying something so absolutely out of his nature.

A smile crossed his lips and he hurried ahead to Reggie, quickly but quietly. As he stepped up close, he laid a hand on the back of her thigh and started to caress it upwards, heading for her firm, round buttock. "Hey baby, wanna do up to my--"

Suddenly, he was falling back toward the wall. He wasn't even sure what had happened, whether Reggie had kicked him of hip-butted him or what. All he knew was he hit the wall to the sound of her hollering, "What the fuck!"

As he regained himself, he looked back to Reggie -- but, didn't find Reggie. The young woman, who Greg only knew as also living in the building, stepped down off the stool and shot him a sharp look ... and Greg suddenly realized his nuts were hurting again.

 

[ladyoffiction]

Reggie had every intention of returning the next evening and continuing their little lesson. While the sex wasn't exactly the best, she felt that he could be very good if he practiced enough. And since Reggie wasn't seeing anyone, and would remain celibate until she did find someone, she didn't see the harm in project.


Lulu had sort of volunteered to help organize the manager's office. He didn't ask for the help, or even implied that he needed it, but Lulu had seen the disarray the office had been in when she first moved in and she decided that it was her duty to organize it. It was just an average morning of checking to see if everything was in place when a hand touched her thigh. Her eyes widened and without even thinking she shoved the figured away with her shoulder. As he crashed into the wall, she took the opportunity to grab her bag and take the mace out of the small pocket in the front.

"You have 5 seconds to explain what the fuck you were doing before I mace your ass from here to Albuquerque," she said with a slight Spanish accent.

 

[JustABadBoy]

"You have 5 seconds to explain what the fuck you were doing," the young woman said, her voice revealing what Greg automatically took as the sexiest accent he'd ever heard, "before I mace your ass from here to Albuquerque."

"I'm sorry!" he responded quickly, "Really, I am. I thought you were--"

He stopped short of saying Reggie's name. He doubted very much the older college girl would want strangers in the building knowing that she was doing it with a high school senior, even if he was emancipated and paying his own way in the big city.

"I ... thought you were someone else," he explained, very carefully rising, his hands out in a bit of a surrender gesture. Then, the thoughts of the previous night, of the great sex, of his apparently acceptable performance, and of his burning need to get more ... they all combined to bring out the Devil resting on his shoulder. He smirked and dropped his eyes to her long, lovely legs, then looked back to her face and said suggestively, "But I'm happy to find you're exactly who you are." He thrust his hand out -- without getting any closer to the mace-packing mama -- and announced, "I'm Greg. Can I buy you a truce coffee...?"

 

[ladyoffiction]

Lulu looked the man over. Or boy really. If she had to guess his age, she would say he was about 16 or 17. She didn't remember any families living in the building, but it wasn't as if she knew everyone in the building. She had seen him around the building, which caused her to lower the mace slightly. Macing a neighbor--even a horny teenage neighbor--was a bad idea.

Her eyebrows shot up as he checked her out and asked her out for coffee. "Are you fucking serious?" she snapped. She threw her hands up in the air, rattling off a number of swear words in Spanish. "You try to grab my ass, mistaking me for someone else and you ask me out for coffee? How old are you anyways? 16? Go home to your mother or I'll kick your ass." She grabbed her purse and stomped off, going up the stairs to her apartment. Who was that kid and what the hell was he thinking?

((We'll bring Lulu back later. She and Reggie are friends, so we'll probably be able to get a threesome.))

 

[JustABadBoy]

Greg was stunned, not just by the woman's reaction or the foul words in her native tongue that he thought he could pick out, but also by her comment about his age. As he watched her ascent the stair case -- watched that lovely, tight ass, as everything connected to it also ascended the staircase -- Greg wondered, Do I really look that young...? Or was she just mad?

He figured it was the latter. No one at school every called him 16 or 17. Of course, most everyone at school was 16 or 17...

 

[ladyoffiction]

Work as a waitress wasn't particularly satisfying nor was the pay the best, but it paid the bills and the tips were decent. every Thursday a group of elderly men would come in. They harmlessly flirted with Reggie and if Reggie flirted back, their tips were quite generous. After work, she drove home and freshened up a bit before going over to Greg's apartment. She knocked on the door and waited patiently for him to answer.

 

[JustABadBoy]

Greg was ready. Very ready. He'd skipped out of last period and caught three different buses to get to his 22 year old cousins house, where he snatched up a bottle of wine and a couple of 22 ounce German beers, stuffing them into a back pack and reversing his route to get home in time to be ready for Reggie.

At the sound of her knock, he hurried around the apartment checking it once again. You're ready, relax. Get the door, then get busy. You can do this.

He answered the door wearing a button up shirt, loose slacks with no belt, and slip on shoes, all things that could be easily discarded when the heat began rising. Greg presumed that they'd be fucking soon; he'd thought of nothing but having Reggie all day.

Well ... that wasn't exactly true, of course. For a good portion of the morning, he'd also thought of the Latina who lived somewhere upstairs...

As he opened the door, smiling broadly at Reggie and remembering all the new things he wanted to do with her tonight, he remembered what his Grandfather had always told him about a bird in the hand. As he looked Reggie over, he thought, wonder what it would be like to have two "birds" in the same bush...

(OOC -- That last line is just him thinking. Not trying to rush to a threesome, although if we do get there, it will be fun to write.)

 

[ladyoffiction]

Reggie smiled back at him as he opened the door, stepping inside his apartment. She was wearing a simple t-shirt and shorts, showing off her long legs. She looked him over, appreciating the view. "Hi," she said, leaning in and kissing his cheek. "How was school?" She was being polite, trying to get him to talk more. He seemed to be rather quiet and withdrawn. She kicked off her shoes and moved over to the couch, sitting down.

"Learn lots of useless shit, I hope?"

 

[JustABadBoy]

"Learn lots of useless shit, I hope?"

He watched her saunter through the apartment toward the couch. Her shorts made her legs look even longer than they probably were; Greg wanted to strip her down and, starting at her ankles, kiss ever inch of them all the way up to her pussy and ...

"Yeah," he said, considering her question while also contemplating a question he'd been mulling over for much of the day. He started across the room slowly, ogling her conspicuously. "Hey, um ... I was wondering. Last night was ... wow. And I was just wondering..."

He licked his lips, slow and suggestively, then smiled wide. "Maybe we could try something new...?"

 

[ladyoffiction]

Reggie watched him as he walked around. He looked a bit distracted or at least deep in thought. Perhaps he had a test or project to work on. He seemed like a smart kid, so she doubted she would be able to help with anything like studying. She was good at math, but Greg looked like the type of guy to excel in that subject. Since they had been talking about school, she assumed that he was thinking about something related to school. She was wrong.

She tilted her head to the side at his question, a light smile on her lips. She had sarcastic comment ready at the tip of her tongue, but she decided against it. She didn't want him feeling embarrassed or anything. Standing, she closed the distance between them and ran her hands up his chest. "What do you have in mind?