Lisa Makes a New Friend

Lisa sat laughing and drinking with her group of friends, they had come to a hot new club in downtown Chicago only a short distance from the high end gym where most of them worked... many as trainers. There was always some kind of new pickup place that was hot on Rush or somewhere close to the Gold Coast, basic meat markets. This one was huge with three separate bar areas and a large dance floor and later in the evening usually a live band of some kind. It was a Friday night and the place was packed.

Lisa and her group of about 10 were occupying the corner of the central bar. Lisa was sitting at one end and was occasionally taking a look around to see if she spotted any hot guys. There were the usual types she recognized and was getting tired of... the traders from the Merc... the lawyers... all the young professionals. They were all dressed in the latest stuff, all worked out with perfect haircuts. Lisa caught the bartender's eye and motioned for another gin and tonic. She listened to more of the stories being told, mostly about the clients they had had to put up with during the day. Their gym catered to the most elite clientele in the city and the ridiculous attitudes and demands they could get on a daily basis was almost always good for a story or two. Lisa rested her chin on her hand and just smirked while the story was being told.

It was starting to dawn on her that she was getting bored of this entire scene. The same group of friends from work, perfect guys at the latest/hottest pickup joint, the same trainers with the complaining clients or the endless discussion of pecs and glutes and abs. She loved fitness, always had and always would, she just was getting tire of talking about it. A lot of these trainers were as a bad as their clients. Too much talk... not enough action!

Lisa had been an athlete growing up playing every sport that came along in school... her best was gymnastics which she did for 10 years from 8 to 18. Now, at 29 and 7 years out of college, she trained mostly wealthy fat people who wanted to look good without effort, thinking their money could replace the hard work it really took to get in shape. It would be nice to get someone to walk through the gym door for training who had the right motivation.

Lisa thought about her plan of moving on, she hoped to get her pro card next year and then build her own small training business. But for now she needed to keep on training the skinny wealthy guys... and the fat wealthy women. It was a pretty depressing prospect.

Lisa suppressed a yawn... thanked the bartender as her second (or was it the third?) drink arrived and shifting her head back to the crowd, still with her head on her hand, she caught site of something unusual.

There amongst the crowd of Chicago's hottest singles was the smallest, meekest little guy she'd seen in... well just about forever. He looked like they could have cast him as the skinny Steve Rogers before the science experiment. She smiled at the thought, she loved all the Marvel movies and had seen them all a dozen times probably.

She continued to watch him make his way across the almost shoulder-to-shoulder crowded room. He had a coat and tie on but the shirt was a bit too large for his thin neck and gathered too much with his tie and the jacket hung on him like a sack. It looked like something he'd gotten second hand. His hair was buzz cut really short and he had on black horn-rimmed glasses. He looked to be about 5' 7" or so. She chuckled as she thought his weight couldn't be more than about 130 pounds. She was examining him with her professional trainer-eye... which had gotten pretty expert over the years at analyzing what she had to work with in regard to new clients. There wasn't much to work with on this guy. She chuckled to herself.

She had completely tuned out her friends who continued to entertain one another, all of them quickly getting drunk. No one noticed her laser focus on the small, unassuming young man working his way across the room. It took him forever to move any distance he'd tap the taller guys and girls on the shoulder, then try and squeeze his way through as most just glanced at him and then ignored him. It looked like he was heading in her general vicinity of the bar. She now could spot more of his features. He had a boyish quality about him that she found appealing. Just off the farm she thought. He seemed so out of place. He was a minnow in a shark tank. She had his narrative already figured out... young guy fresh in town from the country... out after work. He'd probably asked a co-worker where he could go and of course got the name of this place. His co-worker neglected to tell him that the mercenary MILFs and the aggressive young professional women in here would literally chew a guy like him up and spit him out. He didn't stand a chance.

He came around the corner of the bar and Lisa found herself strangely hoping he would sit in one of the few open stools near her. She thought it would be fun to hit on him and see how he reacted. She was so used to the big arrogant guys at bars like this. She seemed to live with the type 24/7... at the gym... in her building... here at these bars. At about this point with perfect timing some guy that looked like he just stepped out of an Abercrombie commercial sidled up next to her blocking her view.

The man ordered a craft beer of some kind and then smiled at her. She waited for the line. She was not smiling... she gave him her strongest... get lost look. Hey babe, you look lonely. She rolled her eyes. I'm really not interested tonight, you should cut your losses now and try someone else. He continued to smile but something about her look made him take her advice. Your loss honey. He sauntered away. How did she get to this point? She had just turned away a hot, tanned, muscular hunk in order to keep a seat open for a skinny nerd in horn-rimmed glasses.

She looked back toward the bar at this thought to find the object of her interest moving up next to her. He didn't sit next to her but leaned on the bar and tried to get the bartender's attention... to no avail. He kept motioning with his finger but Tina the bartender just kept walking by and not noticing. His shy presence was easy to discount. This happened twice before he spoke up "miss?" Tina missed this too. Lisa smiled to herself. She raised her hand at Tina who immediately came over. "You through that g & t already Lis'... you better slow down girl!" "Nope... I'm good... but this guy here needs one." The young guy turned and looked at her and actually gulped. She smiled at him. "Why don't you have a seat?" She patted the bar stool.

He hesitated for a few seconds and then slowly sat down and said thanks. Lisa decided to turn on all her charm. IT had been a while since she'd been this flirty and it felt good. She crossed her legs allowing her short black dress to slide up even higher exposing almost all of her tanned and muscular dancer's legs. In the same motion she swiveled toward him introduced herself and held out her hand. Their knees were just barely touching. He grabbed her hand... his grip was uncertain and a bit clammy and she could tell he was absolutely scared to death. He would hardly even look her in the eye. His name was Bobby.

"Well bobby...what do you do?" He proceeded to tell her that he was an accountant and worked for one of the big firms in the loop. Lisa peppered him with questions and it didn't take her long to pry out his whole story. He was from a small town in the southern part of the state... had gone to a small community college and had always wanted to live in Chicago. He seemed to loosen up JUST a bit when talking about his background. While he was talking Lisa examined him a bit more. He was if anything actually smaller than she thought. She could tell that under his clothes he was nothing but skin and bones. She couldn't remember the last time she had talked to a guy that was this innocent and inexperienced. She found it refreshing after all of the countless glib jerks.

Lisa had always been attracted to muscular jocks, and until this moment she thought she was just having some fun with the guy in an otherwise boring evening, perhaps helping the poor guy out and providing some better advice than he'd gotten to get him in this joint in the first place. But the more she talked with him and the more she saw how he reacted to her, the more she found herself wanting to carry the experiment farther. She caught him giving her legs and chest furtive little glances. He seemed to have absolutely no experience with girls at all. She clearly scared him to death, and she found her power over him incredibly hot.

Amazingly it had taken her friends this long to finally notice that she had made a little friend. Jim and Susan, who were down near her side of the bar took notice and moved over. She imagined what it must look like to them.

Susan, who was the best trainer in town... in superb shape and an MMA instructor to boot, looked at Bobby with undisguised disgust and then looked at Lisa like she had lost her marbles. Lisa knew she needed to get Bobby and leave before her entire group descended on them. Without thinking too much about it, Lisa grabbed bobby's hand, asked Susan to get the tab for her and pretty much dragged the little guy toward the front door.

Her roommate was out of town on business for a week and her apartment was in a hi-rise very close. She told Bobby that he would not have liked her friends much and then suggested they get a drink and watch some TV back at her place. She didn't' give him a chance to say no. She hailed a cab and pushed him in ahead of her. She told the driver her address (only a couple of blocks). We can go out for some food a bit later if you like, i know some good places. Bobby looked like he needed an explanation so she told him how nice it was to talk to a normal guy for a change. She smiled at him and on a whim she leaned over put her hand on his neck and very slowly planted a soft little kiss on his mouth. She liked the feel of his soft lips.

Still holding his neck firmly she backed off just enough to look him in the eye and then more aggressively she kissed him again... this time exploring his mouth with her tongue. Bobby was totally passive... letting her take complete charge. She basically dominated his mouth, forcing his tongue to go wherever she wanted... all the while holding his neck in an increasingly iron grip as she grew more excited. She found the dominance absolutely incredible. This went on for most of the cab ride. When the cab finally stopped she had to basically unwrap herself from around Bobby. Her body seemed to have a desire to totally dominate the kid. He looked comical... his hair all messed up... her lipstick smeared on his face a bit.

She paid the cab, grabbed bobby's hand and went inside. She lead him into an elevator hardly even acknowledging the doorman. Arriving on the tenth floor and still holding Bobby's hand tightly... she quickly directed him down the hall and let them both in to her apartment. Lisa left him standing in the center of the small living room as she turned on a couple of lamps and then the stereo which began to pump out some low jazz. Lisa moved back to Bobby giving him another mouth dominating kiss... and then began to slowly undress him. He didn't' resist. She took off his sport coat, sliding it down his back and arms and then almost ripped the tie off of his neck. Next she slowly began unbuttoning his shirt which she slid over each of his shoulders and then down is torso. He WAS skin and bones. Attached to his narrow bony shoulders were toothpick arms. She was astonished at how skinny and weak and bright white he was. To her surprise... all she could think about was his reaction when he saw her own physique in comparison.

Next she slowly undid his belt and then unbuttoned his pants and slid the zipper down... never letting her eyes off of his. The pants were loose and simply fell right down around his ankles when she let go of them. To say he had chicken legs would be an insult to chickens. His legs were thin and white and went straight down with no curve or muscle at all. Incredibly he was wearing these tiny white Calvin Klein bikinis but on his emaciated frame they looked pathetic. Lisa felt like a lioness with this guy. She had never wanted a man so badly in her life. She stepped back from him and unzipping her dress she let if fall off standing before him in nothing but a tiny black lace g-string and a matching push-up bra... her tanned muscular gymnast body glistening in the low light. Bobby gave her a slow look up and down... from her athletic muscular legs to her six pack abs to her beautiful shoulders capped with muscle to the cover model face and long blonde hair hanging loose around her shoulders. She raised her arm up and flexed a bicep for him. She saw his knees begin to shake. She was going to totally have her way with this guy and blow his mind. She bit her lip in anticipation.

Bobby's knees were close together and visibly shaking slightly... his hands were straight at his side. She moved up close to him again and wrapped her arms around him locking her hands in the small of his back and squeezing his body tight up against hers. She loved the feeling of his body giving way to hers. She imagined how it felt to him. As she squeezed him tighter she leaned back just a bit and it took the weight off his feet. His pants were still gathered around his feet. Now his face was just slightly higher than hers and he hesitatingly placed one hand on her shoulder and the other on the back of her other arm. Lisa tightened her tricep knowing that he'd feel the horseshoe shaped muscle expand and define itself under his hand. She brought her mouth close to his again. He was breathing heavy. "Are you okay bobby? Am i moving a little too fast for you?" Bobby had trouble getting enough breath to respond... he simply grunted, "No... I... like... you... so... much." She realized she was squeezing him so tight he could hardly breathe. She loved her control over this guy, her body so outclassed him in beauty and power and muscular aesthetics... it was an incredible feeling for her that she had never experience before.

Lisa kissed him again and letting him back down on his feet she slid her hands down to his naked rear end and squeezed his non-existent glutes. She pressed his groin in tight but could feel almost nothing down there. Backing off she slid a hand around his thin upper thigh and then, pulling back the elastic on his little bikini briefs, she moved her hand onto his crotch and cupped his little "man parts." Bobby stiffened like he had been hit with an electric probe and his hands jumped from her shoulders to her legs. She shivered as he ran his hands frantically down the groove in her legs created by her nice flaring quadriceps muscles.

Lisa discovered he was small down there just like everywhere else. This was the first part of his slight stature that concerned her. She moved her hand up slightly and wrapped her fingers around his limp dick and started to stroke it as best she could. He responded and she could feel him begin to get erect but it wasn't much. She wasn't sure if it was big enough or hard enough to even penetrate her. He continued to rub his hands over the sides of her legs and back up feeling her tight, hard butt. He moved his head over to the side and with his chin resting on her shoulder he whispered in her ear, "I'm a virgin .. I don't know what to do... I'm sorry Lisa."

She just whispered back, "it's alright Bobby."

Lisa considered her options as they stood in her small living room still clutching one another... Bobby's hands continuing to explore Lisa's amazing physique. In a flash she had an idea based on a comment her rather "nutso" roommate had made a few months back. Lisa put her one arm around Bobby's neck then leaning down slightly she slid her other arm under his knees and lifted him up, cradling his body easily in her arms. He naturally moved his arm around her neck to hold on. He was light as a feather. She felt like she could fold him up like a ventriloquist dummy if she had wanted to. His pants were still bunched around his ankles. She walked into her own bedroom and dropped him playfully on the bed. The room was dark with just a slight bit of light coming in from the hall and the living room. "Why don't you get those pants all the way off hun... I'll be right back."

Lisa padded down to her roommates bedroom and rummaged through the nightstand, not finding what she was looking for there. Then she moved to the chest of drawers and there in the bottom drawer in the very back corner she found what she was looking for. She pulled it up and held the black leather straps out to each side. It was a dildo mouth gag. It would completely cover bobby's mouth, replacing it with a wonderful 8 inch long black rubber dick. She imagined what the view would be like for Bobby looking down on that. She smiled. Bobby was not going to be a virgin for much longer she realized and nearly laughed out loud. Her roomie had mentioned some of her kinkier exploits with some of the weirdos she would often bring home and she had thankfully remembered. Who knew that it was going to come in this handy?

She walked back to her bedroom where bobby had removed his pants and now his little briefs. He sat in the bed nervously and Lisa could see that his little erection was there but oh so tiny. She held the gag bunched up in one hand and out of view and then crawled up from the foot of the bed like a predator until she was straddling Bobby's body. She stopped with her legs on either side of his small chest. Leaving the dildo on the bed next to him she put her hands on his soft doughboy belly and then rubbed her hands up his tiny chest... over and around his bony shoulders and then back to his belly. She continued to do this, towering over him, her long blonde hair hanging down and just barely grazing his face. She stared at his eyes and also began to rub her crotch on his little dick, moving it back and forth and thinking perhaps she could coax a little more out of the guy. Lisa was getting incredibly hot and the anticipation was killing her. Every part of Bobby was responding EXCEPT the part that mattered which stayed stubbornly tiny. Lisa leaned back a bit and stared at him... they were both breathing heavy. "Are you enjoying yourself hun?" "Oh yea Lisa... this is the most amazing thing that has ever happened to me. I knew I'd love Chicago!"

Lisa smiled and put her finger on his lips indicating he should be quiet. Then she pulled out the gag and dangled it in front of her and right before his eyes. His mouth dropped and his eyes went wide. "What is that?" "It's something that can provide us both with a lot of pleasure baby. You need to trust me. Ok?"

Bobby simply gulped and nodded. "Good boy!" She moved the harness up close to his face. "Open up wide babe!" Bobby accepted the ball gag in his mouth and Lisa began to strap the harness around his head and worked the straps really tight. She sat back and looked at her handiwork. She smiled. His still wide open eyes were staring cross-eyed at the large dildo now protruding from his face. His eyes moved from it to her. She smiled at him and then moved her butt up and down back and forth slightly on his crotch area again in a circular motion. She supported herself on only one hand on the bed as she moved her other hand to the dildo and began stroking it like she was masturbating him. Then she moved her mouth up to it and sticking her tongue out she began to dramatically lick just the tip all the while staring at Bobby's eyes. Then she took it all in her mouth and began to work back and forth to lubricate it. Their eyes were close... she pulled back out with her lips tight and it made a plopping suction sound as the end popped out of her mouth.