October 25, 2014 Alex studied the teen sitting on the edge of the hotel bed. Emily was short and rail thin with no real curves to her; the long sleeve pink top she wore barely protruded from her chest. The black skirt concealed her pale slender legs down to her ankles which ended in a pair of brown, fleece lined boots that seemed to be popular with females during the fall and winter. Emily shifted her hands about in her lap and gave him a nervous smile. Her blue eyes peered expectantly from behind her black rimmed oval glasses. Her cheeks were rosier than the faint traces of teenage acne could account for. Black hair framed a round face and barely brushed the tops of her shoulders. A hand lifted and brushed a wild strand from her face, and Alex caught a glimpse of the black wrist braces she wore to help make using her hands easier. Another pair of braces concealed in the boots around her ankles made walking easier.
"You’re very beautiful," he told his neighbor.
Her cheeks reddened. "I’m not beautiful." Emily’s speech could be a challenge to understand when she grew excited or nervous. Alex had known her most of her life and still struggled sometimes.
He raised an eyebrow and moved to sit next to her. For the last few weeks he had reserved a room at the nearby Hampton Inn where they came to fulfill Emily’s part of their agreement. Alex was never sure why he left feeling like Emily was controlling the situation. Like tonight. She had insisted they make love for the first time. Not only would it be the first time together, it would be Emily’s first time, and he found the idea of being the one to take her virginity daunting.
His hand lifted to her cheek and cupped it; her eyes closed, and her face pressed against his palm.
"You are very beautiful," he said softly. "Your skin is soft as silk."
He ran a finger lightly over her dark eyebrow. "Your eyes are like polished sapphires sparkling in candlelight."
He traced the outline of her pink lips. "And your lips are perfect for kissing. Soft. Delicious."
Her chest rose and fell quicker, and the color in her cheek deepened. As his finger brushed her lips, they parted, and he felt her warm breath on his skin.
"Will you kiss me," she whispered.
Carefully he removed her glasses and placed them on the dresser. Wrapping one arm around her waist and placing the other on the back of her head to steady her, he drew her close. She tasted of chocolate from the milkshake she had eaten after dinner. The faint taste of chicken and peppermint from dinner and brushing her teeth. Her arms reached around his body and pulled him closer.
When their lips parted desire shone in her eyes just as Alex knew it must be in his. He wanted her. To feel her. All of her.
Until tonight their physical interactions had been reserved. He had felt her thighs beneath her skirt last week, and Emily had run a hand along the front of his pants to feel his erection. He had cupped her small breasts through her top two weeks earlier. In a way Alex enjoyed the slow, teasing pace they had been going. At night he tried to picture what she must be like; once they went all the way there would be nothing left to imagine. But Emily was eager, and he had forestalled her for as long as he could.
Shakily her hands lifted to the front of his shirt and fumbled unsuccessfully with a button. He took each of her wrists lightly in his hands to steady them. An embarrassed look came across her face when she was still unable to undo it. Alex sighed inwardly. Some days her cerebral palsy was better than others.
Alex leaned back and took his time undoing the buttons. When the last one was open, he guided her hands to the collar of his shirt. Her eyes gleamed as she pushed his shirt from his shoulders to expose his white undershirt. She did not have problems taking the hem of it and pulling it up so that he sat bare chested before her. Her eyes went wide.
They sat there in silence before Emily leaned forward and kissed him again. This time her hands ran along his skin; the rough feel of her braces contrasted with the softness of her fingers. He broke the kiss and took one of her hands. The sound of the Velcro being undone filled the silence. First one and then the other of her wrist braces were removed and dropped into the floor atop his shirt; he pulled her close and resumed the kiss.
Her hands felt cool as they glided along his back. Her kisses grew more ardent the longer she explored his body, especially when the tips of her fingers dipped into the waist of his pants. His manhood strained against its prison; it yearned to be free and to explore her body.
Emboldened, Alex slipped his hand beneath the back of her top and traced her spine up to the band of her bra. She stiffened in his arms and froze. After a moment’s hesitation, she moved back from him and met his eyes. Cautiously, like one might approach a deer in the forest, he took the hem of her shirt and lifted it to expose a pale stomach. As the shirt rose, her ribs came into view. Despite a voracious appetite, Emily looked underweight. Her eyes squeezed closed when the shirt moved up to expose a nearly flat chest encased in a black lace bra. She lifted her arms over her head to allow him to pull the top off.
As soon as it was off Emily crossed her arms across her breasts. Taking her hands, Alex moved them to his sides so he could study her. Compared to him, she looked so small. At eighteen, she was shorter and more petite than other girls her age.
Her skin felt so cool when pressed against him. They resumed their kiss while learning the feel of one another. It was all he could do not to just press her down and climb atop her.
A tug at his waist made him open his eyes and look down to see her fingers struggling with his belt. He helped unbuckle it and let her pull it free from its loops. Then she started working on the button to the front of his pants.
At forty-three Alex was just a bit overweight. He ran four times a week and ate relatively healthy, but his weight plateaued not quite where he wanted. His doctor seemed content with his weight and blood pressure and did not say he should lose more. He suspected if he gave up his chocolate addiction that he would shed a few more pounds, but it was hard to do. He loved chocolate. Now, when faced with this slender young woman, he was all too conscious of those extra pounds, and suddenly the chocolate did not seem that appealing. What would she think when she saw him naked? Emily managed to open his pants and release his eager manhood. His shaft stood out against his underwear, and she was staring at it as if it were a weapon. They sat there silently; Alex watched her, and she watched his manhood. The look on her face said she was having second thoughts.
Alex did not think his penis was large. At best he assumed it was average. None of the women he had been with had commented on its size; of course, there had only been four not counting Emily. Had she ever seen a penis before? Surely she had. Yet, it was probably very different seeing a real one and one on television or the computer.
He was at a loss on what to do next. Should he try to remove her skirt? Kiss her more? Wait? He did not want to rush things and scare her, but he did not want to wait so long that the mood was lost.
The decision was taken from him by her lips pressing to his. He jumped when he felt her fingers brush the tip of his penis through his cotton underwear. The touches were timid and brief. He slid his hand along her side and cupped her breast and held it earning a soft moan. This time he gasped when her fingers closed around his erection.
When the time seemed right Alex stood and allowed his pants to fall to the floor. He kicked off his shoes and stepped out of the pants before tugging his socks off. Her eyes stared wide eyed at the bulge in his white briefs.
Alex lowered himself to one knee by the bed. Her boots slid free easily to display the white braces around her ankles. Once they were removed Alex worked the beige knee high socks off to expose tiny feet with toenails painted pink. Painting her nails was something new that Emily had started once they had decided to enter their strange arrangement.
It was hard to believe, but Emily was his sugar baby.
The idea was preposterous. The two of them had lived next to one another for over a decade. Emily had played with his daughter, and his daughter Lindsey had babysit Emily for a couple of years. During the last three years of high school he had helped her with math and science homework. Now she was a freshman in college; Alex had practically watched her grow up.
Out of the blue Emily had proposed the idea a month earlier. It seemed innocent enough at first with an occasional lunch date and dinner date. Over four weeks things had turned more intimate until their relationship culminated into tonight. Tonight Emily would lose her virginity, and Alex was responsible.
When he sat back on the bed, Emily’s face was the color of a beet. To his surprise she stood, took a deep breath, and pushed the skirt down to her ankles to reveal a pair of black lace panties. A bush of black, curly hair could be seen through the thin material, and his manhood ached in response.
Alex stood with her; his tall body loomed over her short body. His hands were trembling now as they reached to the front of her bra and unclasped it. The garment joined the other clothes in the floor, but his eyes were fixed on her breasts. They were more or less bumps with nipples and light brown areolas. Never had he seen such small breasts. They were fascinating.
Emily’s hands rose and crossed over them self-consciously. Alex gave her a reassuring smile and embraced her. Their difference in height made it awkward to kiss while standing, and he was painfully aware of his erection pressing into her stomach. Slowly the tension melted from her, and her fingers found the waist of his underwear. Her body moved back to watch his underwear fall, and her eyes widened at the sight of her first penis.
Just as Alex had studied Emily’s breasts, she stood gazing down at the member that was to go in her. Compared to her body, it seemed too big, and for the first time he wondered if he would hurt her. Gingerly her fingertip brushed the tip, and it throbbed in response. If she kept doing that he would climax before they ever had sex! Then she giggled! Actually giggled! His cheeks heated, and he realized how she must have felt earlier.
A smile covered her face. Emily was beautiful when she smiled, and he thought he could watch her all day just smiling. It was not the forced smile that people sometimes gave when trying to put on a positive face on an unpleasant situation. This was a smile that said she was happy to be here with him at this moment.
It was his turn to watch wide eyed as she slid her panties off and stood there with her arms to her side as if posing. For the first time he gazed at her completely nude body, and it struck him that he was the first man to see her naked. Her skin was pale and appeared to glow in the soft light of the electric candles they had scattered about the room. It was rare to see her in anything other than a long skirt or jeans, and he had his first good look at her legs. They were slender and smooth and unlike any other he had seen. They looked frail and almost too thin. A thick patch of untrimmed black hair covered the area between her legs.
Alex stepped forward and pressed her body to his. It felt strange holding her. The first time with a new lover always felt strange, but for some reason this felt even stranger.
"You are incredibly sexy," he whispered into her hair.
She pulled him closer causing his penis to press harder into her. "So are you."
Alex led her to the side of the bed, and he climbed to the center so she could stretch out next to him on her back. With his head propped on his hand, he trailed a hand down her body. Emily did not stop him when his fingers brushed her pubic hair.
"You don’t have hair down there," she said in a nervous voice. "I thought everyone did."
"I prefer it shaved. It gets itchy in the summer." He refrained from telling Emily that his last girlfriend preferred it that way when she performed oral sex.
Emily considered this. "Do you want me to shave down there?"
Alex did but shook his head not wanting to spoil the moment. "Maybe later." His hand caressed her pubic hair, and her thighs parted slightly when his hand dipped between her legs. She was damp but not wet. Perhaps he should have brought KY Jelly. A large tube was stored in his nightstand as Linda, his previous girlfriend, had always needed it during intercourse.
Her eyes bulged when he let his finger slip between her labia, and her hand moved his away from between her legs. Her body trembled slightly.
"Are you okay," he asked.
"I.. I don’t…" Her mind struggled to put words together in a coherent thought. "I’m just not ready for that."
He kissed her lightly on the lips. "That’s okay. You have to tell me what you like and don’t."
"What do you like?"
What he wanted more than anything at that moment was to stretch out on her and fill her with his shaft. What he said instead was "I like a lot of different things."
"Like what?"
His hand moved to cup one of her breasts. "I like touching your breasts."
She smiled and blushed. "What about kissing them?"
"I don’t know. I’ve never tried."
Emily gave a giggle that made him painfully aware of her youth and how much older he was than she. God! She’s younger than my daughter!
"You could try. If you want."
For answer Alex leaned over and kissed the base of her breast. Slowly he made a circuit around it before moving to the other breast and then returned to the first. His mouth made a moist trail spiraling around first one breast and then the other until it reached her nipple. Emily gasped and then moaned; her back arched as his mouth closed around the nub and kissed. Her fingers clawed at the bedspread until he released it.
She lay panting for a long moment before asking, "And?" That seemed all she could say.
"I like it a lot."
"What else do you like," she asked breathily.
"I like touching you." To suit his words he ran his hand down one side of her body and along a leg, then back up to repeat the process for the other side. "And kissing you."
Alex kissed her lips. This time he did so only briefly before moving to her cheek. Her head tilted as his lips traveled down her neck to her shoulder. He continued across her chest and only made one lap around each breast before finding his way to her stomach. Suddenly her hands grabbed his head when his lips first touched her pubic hair.
"Don’t."
Alex turned his head to rest it on her stomach so he could look up at her.
"I just… I don’t want to do that. Not right now. Is that okay?"
He sighed. Not because she had stopped him, but because of her attitude. "Emily. Look. Don’t apologize or feel bad about telling someone to stop if they are doing something you don’t like."
"I just don’t want you to be disappointed."
He sighed again. "How can I be disappointed? Not many guys my age are asked to make love to a beautiful young woman less than half his age. If we stopped right now I would not be disappointed."
Emily beamed. "Do you want me?"
Alex laughed so hard tears formed in his eyes. When he could finally speak he answered "I want you so much it hurts. It is all I can do not to just take you!"
Emily gave what he supposed was meant to be a luring smile. "I don’t want to hurt you. Maybe you should get on top of me."
He climbed from the bed and retrieved the folded white sheet he had brought. He left it folded and placed it on the center of the bed before helping Emily atop it. His anxiety grew as he realized what he was about to do.
Emily looked just as nervous but parted her thighs so he could lie between them. It looked as if they strained to widen enough to accommodate him. Looking into her blue eyes he saw his own worries.
"Are you sure," he asked.
Emily nodded. "Do you want to?"
"If you do, I do. If you want to stop, we can." A part of him hoped she would.
For a moment it appeared that Emily might say to stop. Instead she wrapped her arms around his neck. "I want you."
The tip of his manhood penetrated her nether lips and found the opening to her womanhood. She was moist but not as much as he had thought. Again he wondered if they should wait. Carefully he pressed forward.
A grimace covered Emily’s face.
"Are you okay," he asked.
She only nodded.
"Do you need me to stop?"
She shook her head.
Her opening was tight. For a moment Alex wondered if he was sticking it in the wrong place. That would definitely be embarrassing and painful. His hand reached between them and felt to confirm that his shaft was going the right way.
Satisfied he was, Alex gave a gentle thrust.
"Ow! Ow! Ow!" Emily clawed his back and writhed beneath him. Tears brimmed in her closed eyes. "Ow!"
Alex stopped and gave the girl beneath him a worried look.
"It hurts," she gasped.
When he started to pull free, she held him. "Don’t stop."
"We can wait," Alex assured her.
"I don’t want to."
Slowly he pushed into her until he hips were pressed against her. Emily’s face was a mask of discomfort, and he felt bad. Only the press of her hands on his back and the lifting of her hips made him continue.
"I think we should stop," he said.
"Hold me," she said.
Alex lay atop her trying to hold her while shifting his weight so he was not crushing her. Emily wrapped her legs around him and held him in her. Her body clenched his shaft tightly.
"Do you trust me," he whispered.
"Always," came a soft reply.
"May I have your hand?"
Her hand moved from his back so he could grip it. Shifting to make room between them he slid her hand between their bodies, and her body tensed.
"Will you try something for me?"
She nodded reluctantly.
"I would like for you to touch yourself. Down there."
Her mouth opened, and Alex thought she would protest. After a moment, her hand slid on its own to her nether region.
"How does it feel," he asked.
"Weird."
"Have you ever done this before?"
Her face reddened and her head shook vehemently.
Alex simply lay there and felt her beneath him. His eyes watched her face. The tension slowly changed to what might have been surprise. The motion of her fingers changed from stiff jerks to gentle circles now. Her lips parted.
"How does it feel now?"
"It tingles…" Her voice was filled with awe. "It tingles… A lot."
His patience paid off. Emily’s body relaxed, and he could feel her dampness growing. When he pulled backward, much of the friction was gone. Just short of pulling free, he slid forward. It was definitely better. Emily’s finger continued to move.
The teen lay beneath him with eyes closed and look of pleasure on her face. The anxiety was mostly gone now, and her hips moved to a rhythm of their own. Alex tried to match his thrusts to her motions, but it was nearly impossible.
"Oh… Oh…" Emily’s hips lifted from the bed. "Oh…" Her body trembled against him.
It was just too much. Alex groaned and felt his seed flow in bursts into Emily. A primal urge took over, and he thrust his full length into her. He pulled almost free and thrust again.
Emily cried out. Her hand shot from between her legs and clutched him at the same moment her legs wrapped around his body. She convulsed against him.
"Oh god! Oh god!" She repeated it over and over into his shoulder.
Then it felt like she melted. Her hands and legs released him, and her body plopped onto the bed. Her breasts rose and fell rapidly, and her blue eyes stared up at him in amazement.
"Oh shit," she said with a final shudder.
Alex’s eyes widened, and his mouth dropped open. He had never heard Emily curse before. In fact he would have been less shocked if his daughter had. When Emily saw his face, she blushed.
"Sorry."
His manhood lost its hardness and slipped free earning a disappointed moan from Emily. He stretched out on his back next to her and guided her head to rest on his shoulder. The teen snuggled close to him and gave a contented sigh.
"That was perfect," she said and hugged him tightly.
Alex relaxed at the tone of her voice; she sounded genuinely pleased. A thought came to him, and he rose slightly to look down. The only spots of the sheet were from his semen; there were no bloody spots.
They lay in silence listening to each other breath and the din of the traffic outside. Alex closed his eyes and sighed in relief that this was over; the next time would be less stressful. Each subsequent time would be easier.
The sound of an alarm jerked Alex from sleep suddenly. The sound came from his iPhone sitting on the nightstand, and he awkwardly groped for it with the arm not pinned by Emily’s sleeping body. How she was sleeping through the noise amazed him. Earlier he had set his alarm for nine as Emily said she needed to be home by ten. Such an early curfew frustrated her, but Alex empathized with her parents. He could remember his daughter being this age, and the thought of her doing something like this made him cringe.
Emily lay on her stomach with the comforter pulled over her naked form, which only half covered him. It reminded him too much of being married to his ex-wife, the blanket thief.
"Time to wake up," he said and gave Emily a kiss on her head.
She grumbled something but did not stir. Gently he turned her onto her side.
"Emily, time to get up."
Again, she grumbled and rolled back onto her stomach while pulling the comforter over her head. Alex fought down a surge of frustration. He climbed from the bed and crossed to the other side of the bed where he sat and uncovered his sleeping lover. He rolled her onto her back and gave her a gentle shake.
"Emily, time to get up."
This time when she complained and tried to roll back over he stopped her. "We really need to get up."
Her eyes opened slowly and took him in. "Do we have to? I was so comfy."
"I’m afraid so."
Groggily she sat up and blinked the sleep from her eyes. "I wish we didn’t."
They had slept a little over an hour, and Alex felt tired too. Not quite to the extent Emily acted. He found his clothes and dressed quickly. By the time he had tugged his last shoe on, Emily had managed to don her panties, skirt, and socks.
"Here." He held up her bra. She blushed but let him slip the lacy garment over her arms and fasten it closed.
"I must be Cinderella and you my Prince Charming," she said with a laugh when he knelt to replace her ankle braces and boots.
"Not quite. Cinderella was never as beautiful as you."
It looked as if all the blood in her body rushed to her head, and she gave a self-deprecating laugh. "I’m not beautiful."
"I think you are, and I think I am the luckiest man in the world right now."
Her blush deepened, but instead of commenting, a huge smile covered her face.
They collected their belongings and checked the room one final time before leaving. They took the elevator to the first floor but left the hotel through a side door rather than deal with questions from the woman working at the front counter.
"Oh shit," Emily said when she climbed into the passenger seat of Alex’s van.
"What’s wrong?" Alex hoped her cursing was not going to be a habit.
"I’m bleeding."
How she knew, he could not tell since it was dark. Alex kept a lookout while Emily changed into the spare panties and used the emergency pad from the van’s glove box. His daughter kept a couple in there for times when she forgot to bring one; Alex would need to remember to replace it to keep from answering questions the next time she borrowed his van.
They stopped on the way home at Sonic and bought another milkshake. They passed some time in the parking lot chatting so that it was 9:42 when they reached his house.
Alex walked Emily across the lawn to her house next door. It was hard not to hold her hand or kiss her goodnight. That had been one of her stipulations – no public affection or anything that hinted that they were more than friends.
"I guess I will see you on Wednesday?" he asked. Wednesdays were their "tutoring nights". Normally they just had dinner, and he helped her with homework if she needed it.
"Or Tuesday."
"Perhaps," he agreed. While he was on campus Tuesdays and Thursdays for his sole graduate class, his class ended thirty minutes before Emily’s next class which made it difficult to see one another. By the time her class was over Alex was twenty miles away at work.
Emily opened the door and started in. "Bye," she called over her shoulder with a knowing grin.
Then the door closed, and Alex stood outside wondering what he had gotten himself into.
alex2347
"You’re very beautiful," he told his neighbor.
Her cheeks reddened. "I’m not beautiful." Emily’s speech could be a challenge to understand when she grew excited or nervous. Alex had known her most of her life and still struggled sometimes.
He raised an eyebrow and moved to sit next to her. For the last few weeks he had reserved a room at the nearby Hampton Inn where they came to fulfill Emily’s part of their agreement. Alex was never sure why he left feeling like Emily was controlling the situation. Like tonight. She had insisted they make love for the first time. Not only would it be the first time together, it would be Emily’s first time, and he found the idea of being the one to take her virginity daunting.
His hand lifted to her cheek and cupped it; her eyes closed, and her face pressed against his palm.
"You are very beautiful," he said softly. "Your skin is soft as silk."
He ran a finger lightly over her dark eyebrow. "Your eyes are like polished sapphires sparkling in candlelight."
He traced the outline of her pink lips. "And your lips are perfect for kissing. Soft. Delicious."
Her chest rose and fell quicker, and the color in her cheek deepened. As his finger brushed her lips, they parted, and he felt her warm breath on his skin.
"Will you kiss me," she whispered.
Carefully he removed her glasses and placed them on the dresser. Wrapping one arm around her waist and placing the other on the back of her head to steady her, he drew her close. She tasted of chocolate from the milkshake she had eaten after dinner. The faint taste of chicken and peppermint from dinner and brushing her teeth. Her arms reached around his body and pulled him closer.
When their lips parted desire shone in her eyes just as Alex knew it must be in his. He wanted her. To feel her. All of her.
Until tonight their physical interactions had been reserved. He had felt her thighs beneath her skirt last week, and Emily had run a hand along the front of his pants to feel his erection. He had cupped her small breasts through her top two weeks earlier. In a way Alex enjoyed the slow, teasing pace they had been going. At night he tried to picture what she must be like; once they went all the way there would be nothing left to imagine. But Emily was eager, and he had forestalled her for as long as he could.
Shakily her hands lifted to the front of his shirt and fumbled unsuccessfully with a button. He took each of her wrists lightly in his hands to steady them. An embarrassed look came across her face when she was still unable to undo it. Alex sighed inwardly. Some days her cerebral palsy was better than others.
Alex leaned back and took his time undoing the buttons. When the last one was open, he guided her hands to the collar of his shirt. Her eyes gleamed as she pushed his shirt from his shoulders to expose his white undershirt. She did not have problems taking the hem of it and pulling it up so that he sat bare chested before her. Her eyes went wide.
They sat there in silence before Emily leaned forward and kissed him again. This time her hands ran along his skin; the rough feel of her braces contrasted with the softness of her fingers. He broke the kiss and took one of her hands. The sound of the Velcro being undone filled the silence. First one and then the other of her wrist braces were removed and dropped into the floor atop his shirt; he pulled her close and resumed the kiss.
Her hands felt cool as they glided along his back. Her kisses grew more ardent the longer she explored his body, especially when the tips of her fingers dipped into the waist of his pants. His manhood strained against its prison; it yearned to be free and to explore her body.
Emboldened, Alex slipped his hand beneath the back of her top and traced her spine up to the band of her bra. She stiffened in his arms and froze. After a moment’s hesitation, she moved back from him and met his eyes. Cautiously, like one might approach a deer in the forest, he took the hem of her shirt and lifted it to expose a pale stomach. As the shirt rose, her ribs came into view. Despite a voracious appetite, Emily looked underweight. Her eyes squeezed closed when the shirt moved up to expose a nearly flat chest encased in a black lace bra. She lifted her arms over her head to allow him to pull the top off.
As soon as it was off Emily crossed her arms across her breasts. Taking her hands, Alex moved them to his sides so he could study her. Compared to him, she looked so small. At eighteen, she was shorter and more petite than other girls her age.
Her skin felt so cool when pressed against him. They resumed their kiss while learning the feel of one another. It was all he could do not to just press her down and climb atop her.
A tug at his waist made him open his eyes and look down to see her fingers struggling with his belt. He helped unbuckle it and let her pull it free from its loops. Then she started working on the button to the front of his pants.
At forty-three Alex was just a bit overweight. He ran four times a week and ate relatively healthy, but his weight plateaued not quite where he wanted. His doctor seemed content with his weight and blood pressure and did not say he should lose more. He suspected if he gave up his chocolate addiction that he would shed a few more pounds, but it was hard to do. He loved chocolate. Now, when faced with this slender young woman, he was all too conscious of those extra pounds, and suddenly the chocolate did not seem that appealing. What would she think when she saw him naked? Emily managed to open his pants and release his eager manhood. His shaft stood out against his underwear, and she was staring at it as if it were a weapon. They sat there silently; Alex watched her, and she watched his manhood. The look on her face said she was having second thoughts.
Alex did not think his penis was large. At best he assumed it was average. None of the women he had been with had commented on its size; of course, there had only been four not counting Emily. Had she ever seen a penis before? Surely she had. Yet, it was probably very different seeing a real one and one on television or the computer.
He was at a loss on what to do next. Should he try to remove her skirt? Kiss her more? Wait? He did not want to rush things and scare her, but he did not want to wait so long that the mood was lost.
The decision was taken from him by her lips pressing to his. He jumped when he felt her fingers brush the tip of his penis through his cotton underwear. The touches were timid and brief. He slid his hand along her side and cupped her breast and held it earning a soft moan. This time he gasped when her fingers closed around his erection.
When the time seemed right Alex stood and allowed his pants to fall to the floor. He kicked off his shoes and stepped out of the pants before tugging his socks off. Her eyes stared wide eyed at the bulge in his white briefs.
Alex lowered himself to one knee by the bed. Her boots slid free easily to display the white braces around her ankles. Once they were removed Alex worked the beige knee high socks off to expose tiny feet with toenails painted pink. Painting her nails was something new that Emily had started once they had decided to enter their strange arrangement.
It was hard to believe, but Emily was his sugar baby.
The idea was preposterous. The two of them had lived next to one another for over a decade. Emily had played with his daughter, and his daughter Lindsey had babysit Emily for a couple of years. During the last three years of high school he had helped her with math and science homework. Now she was a freshman in college; Alex had practically watched her grow up.
Out of the blue Emily had proposed the idea a month earlier. It seemed innocent enough at first with an occasional lunch date and dinner date. Over four weeks things had turned more intimate until their relationship culminated into tonight. Tonight Emily would lose her virginity, and Alex was responsible.
When he sat back on the bed, Emily’s face was the color of a beet. To his surprise she stood, took a deep breath, and pushed the skirt down to her ankles to reveal a pair of black lace panties. A bush of black, curly hair could be seen through the thin material, and his manhood ached in response.
Alex stood with her; his tall body loomed over her short body. His hands were trembling now as they reached to the front of her bra and unclasped it. The garment joined the other clothes in the floor, but his eyes were fixed on her breasts. They were more or less bumps with nipples and light brown areolas. Never had he seen such small breasts. They were fascinating.
Emily’s hands rose and crossed over them self-consciously. Alex gave her a reassuring smile and embraced her. Their difference in height made it awkward to kiss while standing, and he was painfully aware of his erection pressing into her stomach. Slowly the tension melted from her, and her fingers found the waist of his underwear. Her body moved back to watch his underwear fall, and her eyes widened at the sight of her first penis.
Just as Alex had studied Emily’s breasts, she stood gazing down at the member that was to go in her. Compared to her body, it seemed too big, and for the first time he wondered if he would hurt her. Gingerly her fingertip brushed the tip, and it throbbed in response. If she kept doing that he would climax before they ever had sex! Then she giggled! Actually giggled! His cheeks heated, and he realized how she must have felt earlier.
A smile covered her face. Emily was beautiful when she smiled, and he thought he could watch her all day just smiling. It was not the forced smile that people sometimes gave when trying to put on a positive face on an unpleasant situation. This was a smile that said she was happy to be here with him at this moment.
It was his turn to watch wide eyed as she slid her panties off and stood there with her arms to her side as if posing. For the first time he gazed at her completely nude body, and it struck him that he was the first man to see her naked. Her skin was pale and appeared to glow in the soft light of the electric candles they had scattered about the room. It was rare to see her in anything other than a long skirt or jeans, and he had his first good look at her legs. They were slender and smooth and unlike any other he had seen. They looked frail and almost too thin. A thick patch of untrimmed black hair covered the area between her legs.
Alex stepped forward and pressed her body to his. It felt strange holding her. The first time with a new lover always felt strange, but for some reason this felt even stranger.
"You are incredibly sexy," he whispered into her hair.
She pulled him closer causing his penis to press harder into her. "So are you."
Alex led her to the side of the bed, and he climbed to the center so she could stretch out next to him on her back. With his head propped on his hand, he trailed a hand down her body. Emily did not stop him when his fingers brushed her pubic hair.
"You don’t have hair down there," she said in a nervous voice. "I thought everyone did."
"I prefer it shaved. It gets itchy in the summer." He refrained from telling Emily that his last girlfriend preferred it that way when she performed oral sex.
Emily considered this. "Do you want me to shave down there?"
Alex did but shook his head not wanting to spoil the moment. "Maybe later." His hand caressed her pubic hair, and her thighs parted slightly when his hand dipped between her legs. She was damp but not wet. Perhaps he should have brought KY Jelly. A large tube was stored in his nightstand as Linda, his previous girlfriend, had always needed it during intercourse.
Her eyes bulged when he let his finger slip between her labia, and her hand moved his away from between her legs. Her body trembled slightly.
"Are you okay," he asked.
"I.. I don’t…" Her mind struggled to put words together in a coherent thought. "I’m just not ready for that."
He kissed her lightly on the lips. "That’s okay. You have to tell me what you like and don’t."
"What do you like?"
What he wanted more than anything at that moment was to stretch out on her and fill her with his shaft. What he said instead was "I like a lot of different things."
"Like what?"
His hand moved to cup one of her breasts. "I like touching your breasts."
She smiled and blushed. "What about kissing them?"
"I don’t know. I’ve never tried."
Emily gave a giggle that made him painfully aware of her youth and how much older he was than she. God! She’s younger than my daughter!
"You could try. If you want."
For answer Alex leaned over and kissed the base of her breast. Slowly he made a circuit around it before moving to the other breast and then returned to the first. His mouth made a moist trail spiraling around first one breast and then the other until it reached her nipple. Emily gasped and then moaned; her back arched as his mouth closed around the nub and kissed. Her fingers clawed at the bedspread until he released it.
She lay panting for a long moment before asking, "And?" That seemed all she could say.
"I like it a lot."
"What else do you like," she asked breathily.
"I like touching you." To suit his words he ran his hand down one side of her body and along a leg, then back up to repeat the process for the other side. "And kissing you."
Alex kissed her lips. This time he did so only briefly before moving to her cheek. Her head tilted as his lips traveled down her neck to her shoulder. He continued across her chest and only made one lap around each breast before finding his way to her stomach. Suddenly her hands grabbed his head when his lips first touched her pubic hair.
"Don’t."
Alex turned his head to rest it on her stomach so he could look up at her.
"I just… I don’t want to do that. Not right now. Is that okay?"
He sighed. Not because she had stopped him, but because of her attitude. "Emily. Look. Don’t apologize or feel bad about telling someone to stop if they are doing something you don’t like."
"I just don’t want you to be disappointed."
He sighed again. "How can I be disappointed? Not many guys my age are asked to make love to a beautiful young woman less than half his age. If we stopped right now I would not be disappointed."
Emily beamed. "Do you want me?"
Alex laughed so hard tears formed in his eyes. When he could finally speak he answered "I want you so much it hurts. It is all I can do not to just take you!"
Emily gave what he supposed was meant to be a luring smile. "I don’t want to hurt you. Maybe you should get on top of me."
He climbed from the bed and retrieved the folded white sheet he had brought. He left it folded and placed it on the center of the bed before helping Emily atop it. His anxiety grew as he realized what he was about to do.
Emily looked just as nervous but parted her thighs so he could lie between them. It looked as if they strained to widen enough to accommodate him. Looking into her blue eyes he saw his own worries.
"Are you sure," he asked.
Emily nodded. "Do you want to?"
"If you do, I do. If you want to stop, we can." A part of him hoped she would.
For a moment it appeared that Emily might say to stop. Instead she wrapped her arms around his neck. "I want you."
The tip of his manhood penetrated her nether lips and found the opening to her womanhood. She was moist but not as much as he had thought. Again he wondered if they should wait. Carefully he pressed forward.
A grimace covered Emily’s face.
"Are you okay," he asked.
She only nodded.
"Do you need me to stop?"
She shook her head.
Her opening was tight. For a moment Alex wondered if he was sticking it in the wrong place. That would definitely be embarrassing and painful. His hand reached between them and felt to confirm that his shaft was going the right way.
Satisfied he was, Alex gave a gentle thrust.
"Ow! Ow! Ow!" Emily clawed his back and writhed beneath him. Tears brimmed in her closed eyes. "Ow!"
Alex stopped and gave the girl beneath him a worried look.
"It hurts," she gasped.
When he started to pull free, she held him. "Don’t stop."
"We can wait," Alex assured her.
"I don’t want to."
Slowly he pushed into her until he hips were pressed against her. Emily’s face was a mask of discomfort, and he felt bad. Only the press of her hands on his back and the lifting of her hips made him continue.
"I think we should stop," he said.
"Hold me," she said.
Alex lay atop her trying to hold her while shifting his weight so he was not crushing her. Emily wrapped her legs around him and held him in her. Her body clenched his shaft tightly.
"Do you trust me," he whispered.
"Always," came a soft reply.
"May I have your hand?"
Her hand moved from his back so he could grip it. Shifting to make room between them he slid her hand between their bodies, and her body tensed.
"Will you try something for me?"
She nodded reluctantly.
"I would like for you to touch yourself. Down there."
Her mouth opened, and Alex thought she would protest. After a moment, her hand slid on its own to her nether region.
"How does it feel," he asked.
"Weird."
"Have you ever done this before?"
Her face reddened and her head shook vehemently.
Alex simply lay there and felt her beneath him. His eyes watched her face. The tension slowly changed to what might have been surprise. The motion of her fingers changed from stiff jerks to gentle circles now. Her lips parted.
"How does it feel now?"
"It tingles…" Her voice was filled with awe. "It tingles… A lot."
His patience paid off. Emily’s body relaxed, and he could feel her dampness growing. When he pulled backward, much of the friction was gone. Just short of pulling free, he slid forward. It was definitely better. Emily’s finger continued to move.
The teen lay beneath him with eyes closed and look of pleasure on her face. The anxiety was mostly gone now, and her hips moved to a rhythm of their own. Alex tried to match his thrusts to her motions, but it was nearly impossible.
"Oh… Oh…" Emily’s hips lifted from the bed. "Oh…" Her body trembled against him.
It was just too much. Alex groaned and felt his seed flow in bursts into Emily. A primal urge took over, and he thrust his full length into her. He pulled almost free and thrust again.
Emily cried out. Her hand shot from between her legs and clutched him at the same moment her legs wrapped around his body. She convulsed against him.
"Oh god! Oh god!" She repeated it over and over into his shoulder.
Then it felt like she melted. Her hands and legs released him, and her body plopped onto the bed. Her breasts rose and fell rapidly, and her blue eyes stared up at him in amazement.
"Oh shit," she said with a final shudder.
Alex’s eyes widened, and his mouth dropped open. He had never heard Emily curse before. In fact he would have been less shocked if his daughter had. When Emily saw his face, she blushed.
"Sorry."
His manhood lost its hardness and slipped free earning a disappointed moan from Emily. He stretched out on his back next to her and guided her head to rest on his shoulder. The teen snuggled close to him and gave a contented sigh.
"That was perfect," she said and hugged him tightly.
Alex relaxed at the tone of her voice; she sounded genuinely pleased. A thought came to him, and he rose slightly to look down. The only spots of the sheet were from his semen; there were no bloody spots.
They lay in silence listening to each other breath and the din of the traffic outside. Alex closed his eyes and sighed in relief that this was over; the next time would be less stressful. Each subsequent time would be easier.
The sound of an alarm jerked Alex from sleep suddenly. The sound came from his iPhone sitting on the nightstand, and he awkwardly groped for it with the arm not pinned by Emily’s sleeping body. How she was sleeping through the noise amazed him. Earlier he had set his alarm for nine as Emily said she needed to be home by ten. Such an early curfew frustrated her, but Alex empathized with her parents. He could remember his daughter being this age, and the thought of her doing something like this made him cringe.
Emily lay on her stomach with the comforter pulled over her naked form, which only half covered him. It reminded him too much of being married to his ex-wife, the blanket thief.
"Time to wake up," he said and gave Emily a kiss on her head.
She grumbled something but did not stir. Gently he turned her onto her side.
"Emily, time to get up."
Again, she grumbled and rolled back onto her stomach while pulling the comforter over her head. Alex fought down a surge of frustration. He climbed from the bed and crossed to the other side of the bed where he sat and uncovered his sleeping lover. He rolled her onto her back and gave her a gentle shake.
"Emily, time to get up."
This time when she complained and tried to roll back over he stopped her. "We really need to get up."
Her eyes opened slowly and took him in. "Do we have to? I was so comfy."
"I’m afraid so."
Groggily she sat up and blinked the sleep from her eyes. "I wish we didn’t."
They had slept a little over an hour, and Alex felt tired too. Not quite to the extent Emily acted. He found his clothes and dressed quickly. By the time he had tugged his last shoe on, Emily had managed to don her panties, skirt, and socks.
"Here." He held up her bra. She blushed but let him slip the lacy garment over her arms and fasten it closed.
"I must be Cinderella and you my Prince Charming," she said with a laugh when he knelt to replace her ankle braces and boots.
"Not quite. Cinderella was never as beautiful as you."
It looked as if all the blood in her body rushed to her head, and she gave a self-deprecating laugh. "I’m not beautiful."
"I think you are, and I think I am the luckiest man in the world right now."
Her blush deepened, but instead of commenting, a huge smile covered her face.
They collected their belongings and checked the room one final time before leaving. They took the elevator to the first floor but left the hotel through a side door rather than deal with questions from the woman working at the front counter.
"Oh shit," Emily said when she climbed into the passenger seat of Alex’s van.
"What’s wrong?" Alex hoped her cursing was not going to be a habit.
"I’m bleeding."
How she knew, he could not tell since it was dark. Alex kept a lookout while Emily changed into the spare panties and used the emergency pad from the van’s glove box. His daughter kept a couple in there for times when she forgot to bring one; Alex would need to remember to replace it to keep from answering questions the next time she borrowed his van.
They stopped on the way home at Sonic and bought another milkshake. They passed some time in the parking lot chatting so that it was 9:42 when they reached his house.
Alex walked Emily across the lawn to her house next door. It was hard not to hold her hand or kiss her goodnight. That had been one of her stipulations – no public affection or anything that hinted that they were more than friends.
"I guess I will see you on Wednesday?" he asked. Wednesdays were their "tutoring nights". Normally they just had dinner, and he helped her with homework if she needed it.
"Or Tuesday."
"Perhaps," he agreed. While he was on campus Tuesdays and Thursdays for his sole graduate class, his class ended thirty minutes before Emily’s next class which made it difficult to see one another. By the time her class was over Alex was twenty miles away at work.
Emily opened the door and started in. "Bye," she called over her shoulder with a knowing grin.
Then the door closed, and Alex stood outside wondering what he had gotten himself into.
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