Tom and Reluctant Holly Desi


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Tom unlocked the door to his apartment and held it open for Holly. It was late on a Saturday night, and they had just returned from dinner.

“Thanks for letting me stay her for a bit,” Holly said, smiling. “My roommate’s boyfriend is in town, and she wants the place to herself for a while.”

Tom smiled. “It’s no problem. We can just watch TV. I have a bunch of movies on the shelf. Why don’t you pick one, while I fix us a drink?”

“Sure thing.” Holly smiled as she crouched down in front of Tom’s movie cabinet. Her skirt rode up her thighs, letting Tom see more of her shapely legs. Tom grinned to himself as he took her in. Gorgeous curly red hair, bright green eyes, and a touch of youthful innocence that he found intoxicating. He walked over to the bar, and made a pair of drinks for the two of them. He didn’t skimp on the alcohol.

Holly had already picked out a movie, and was fast forwarding it past the credits when Tom returned. He sat beside her on the couch and handed her the drink, and settled back to watch the movie. He pulled Holly back, so she could lean against him. She smiled appreciatively and snuggled against him.

After the drinks were gone, and they were half way into the movie, Tom pulled her hair off of her shoulder, and gently began kissing her neck. She cooed, a scrunched she shoulders, but didn’t pull away. His kisses started getting a little more intense.

“Tom,” Holly whispered, turning slightly to look at him, “please don’t start this.” Tom responded by grabbing her cheek with one hand, turning her head towards his, and softly kissing her full lips. Holly closed her eyes and moaned. Tom licked her lips through the kiss, and slithered his tongue between them. She parted her mouth to let him in, and he teasingly played with her tongue.

Tom caressed her cheek, and slowly worked his way down her neck. He reached her breasts, and massaged them. She moaned a bit, and tried to push his hand away. Tom’s other arm was behind her body, holding her, and he grabbed her arm with that hand, holding it still. Her other arm was trapped between their bodies, so she was defenseless. She struggled somewhat, but didn’t try very hard. Tom intensified the kiss, and kept up his gently massage.

Tom kept this up for a while, getting Holly used to the feel of his touch. After a while, he began unbuttoning her blouse, so gently that she didn’t even notice. He waited until her entire blouse was unbuttoned before sliding his hand inside. She gasped, and squirmed, but Tom kept her still. She tried to speak, but he kept her mouth covered with his. She lost herself in the kiss, and subsided. Tom went back to massaging her chest, this time caressing the softness of her skin.

His hands went all over her body under her shirt, until it was hanging completely open. His hands travelled all over her front and back. On one trip behind her, he stopped by her bra, and undid the clasp.

Holly’s eyes opened wide, and she broke the kiss with a gasp, shoving him away suddenly. She sat there looking at him, panting, with her hair disheveled, blouse open, and her bra hanging loose, although it still covered her ample chest.

“Tom,” she whimpered, with a touch of fear in her voice, “what are you doing? I told you I wanted to wait until… until…” Her voice trailed off. “Please, I thought you agreed.”

Tom put on his most winning smile, and looked at her sadly. “Holly, are you okay?” He looked at her with concern painted on his face. “You know I would never do anything to hurt you. I wasn’t going all the way. We were just making out. You said that was okay, didn’t you?”

Holly seemed to be having trouble thinking clearly. She was touched by the look of concern on Tom’s face. “Yes, I did say that was okay. But you were going farther than making out!”

Tom looked perplexed. “No, I wasn’t. We weren’t having . I just love the feel of your skin. I wasn’t anywhere near your… your… You know.”

“True,” Holly murmured. Tom could see she was trying to find a flaw in his argument, but the alcohol and ual excitement weren’t exactly conducive to rationality. He leaned closer to Holly, but she backed away, still a little wildeyed. But he kept leaning, and she kept backing, until she was lying on the bed, and Tom was hovering above her. She started to say something, but Tom stopped her with a deep passionate kiss.

Holly struggled, but her heart wasn’t really in it. Tom brushed her blouse off her shoulders and down to her elbows. This left her in a very vulnerable position, trapping her arms at her sides.

Tom broke their kiss, and planted dozens of kisses all over her face. He worked his way to her ear, nibbling on it. “See,” he whispered, “we’re just kissing. There’s no involved. There’s nothing to worry about.” He kissed his way down her neck and onto her shoulder. He moved her loose bra straps off her shoulders, exposing her breasts.

Holly gasped as she felt Tom’s warm mouth cover her breast, softly licking at her nipple. She arched her back, trying to get more of it into his mouth. Tom licked and sucked, getting both nipples completely wet. He didn’t stop until both nipples were extremely hard and sensitive.

Tom stopped, and sat up, leaving Holly whimpering. He took off his shirt, and threw it on the ground, letting Holly see his bare chest. “Wha… what are you doing,” she asked.

“My shirt was feeling a little confining. Doesn’t your feel that way, too?” When she nodded, Tom gently grabbed her upper arms, and sat her up, removing her blouse and bra, leaving her naked from the waist up.

“See, doesn’t that feel better,” Tom asked. He lay down on the couch, in the position Holly had been a moment ago, and pulled her down on top of him. He grabbed the back of her head and pulled her in for a deep kiss. His other arm was around her back, holding her tight against him, flattening her breasts on his chest.

Holly sighed and closed her eyes. She felt safe and secure in his arms. Tom continued his tender caresses. His one leg was positioned under and between hers, and he started to raise it up. It seemed innocent enough to Holly, since he still had his pants on. But the seams on his pants started to rub against the inside of her legs roughly. She started to squirm away from it, but that only succeeded in forcing her skirt to rise higher on her thighs. His leg was still there.

“Tom, please, stop that. Your pants are hurting me.”

Tom looked up at her sorrowfully. “I’m sorry. I had no idea. Let me get rid of them then.” His hands slid from her back to his waist, and he started loosening his pants.

Holly’s eyes went wide. “Tha… that’s not what I meant.”

“Didn’t you say the pants were hurting you?” Holly nodded. “Then if I get rid of them, they’ll stop hurting, right? It’s not like my legs can DO anything, right?”

Holly nodded in confusion. “I guess.”

Tom slid his pants down his legs, and let them fall to the floor beside the couch. Then he pulled Holly back down to him, resuming their kiss. His bare leg went back between her legs, slowly moving up and down. Her skirt kept moving higher and higher, as his leg forced it up her sweet thighs.

When her skirt was up to her hips, Tom stopped caressing her back, and started caress the outside of her nowbare thighs. He slowly worked his way to the back, and then began to caress the inside. As soon as he did, Holly clamped her legs shut, trapping his hand between them.

“That’s far enough,” she muttered into his mouth. She continued to play with his tongue.

Tom sucked on her tongue. “But I’m just caressing you. It’s no worse touching your thighs on the inside than it is on the outside.”

“But still…”

“Besides, you’ll have to open up so I can get my hands out of there.”

Holly seemed to agree with this, and parted her thighs slightly. Tom immediately resumed his caress, working his way higher. On some strokes, his hands rubbed her buttocks, and every now and then, his hands rubbed against the panties covering her vagina. Very shortly, his hands found their way there more and more often. Eventually, he concentrated there, massaging her softly. He could feel the dampness there. They were almost completely soaking wet.

On one stroke, his fingers slipped underneath her panties, as if by accident. Holly tried to sit up, but Tom held her tight. “Tom…” She pleaded.

“Oh god, I’m sorry,” Tom answered. “Your panties are so wet, they just slipped under there.” He tried to remove them, but they seemed to be tangled up in them. In his struggles, his fingers kept rubbing against her clit.

Holly looked at Tom with a cross between anger and pleasure. “Tom,” she began…

“I’m sorry, Holly. They’re just kind of stuck.” He tried again and again, but couldn’t seem to free them. “Maybe it would be better if I just pulled them off.”

Holly shook her head, “No, you can’t.”

“Shall I just leave my hand here then,” he asked. He struggled some more, rubbing forcefully against her clit.

Holly moaned. “No…”

“Then let’s get rid of them.” Before she could answer again, Tom pushed her off him, to the side, with her back on the back of the couch. He pulled his hands down the center of her thighs, dragging the wet panties with them. He grabbed them, and pulled them off her legs, and threw them to the ground.

“There, now isn’t that better?” He grabbed both her face between both hands, and began kissing her again. Very slowly, he repositioned them so that she was lying on her back once again, and her was on top of her. He held her tight, and opened her thighs with his leg. She started to say something, but he shushed her, muffling her protests with his mouth.

Eventually, both of his legs were between hers, and he rutted against her, his manhood still encased in his underwear. Holly relaxed, not caring about anything except for Tom’s tender caresses.

Tom’s rutting stopped, and his hands left her body, even though his kissing intensified. Holly sighed when his hands returned, and massaged her breasts. She didn’t even notice that his hips between her thighs no longer had the feel of his underwear.

Holly did notice when she felt the tip of his cock press against the opening of her vagina. “Tom…” She whispered. “Please don’t…”

“Shhh,” Tom replied. “Don’t worry, you know I won’t do anything to harm you.” With that, he kissed her again, and jerked his hips forward, slowly sliding inside. He reached her maidenhead, and crashed through it violently, until she was completely impaled.

Holly gasped with a guttural moan. Tom remained there for a moment, letting her get used to the feeling of a man within her body. Then he pulled out, leaving only the tip inside, and plunged in again. He fucked her again, and again, and again. Holly kept trying to say something, but the force of his thrusts kept her breath coming in short inaudible gasps.

They kept up their lovemaking for a long time. Holly was so wet and tight that Tom could barely contain himself, but he wanted to hold back. Eventually her noticed the telltale signs. Holly’s face began to get flushed and her breath became shorter and shorter. Suddenly she screamed and thrashed her head from side to side as wave after wave of passion coursed through her body. Tom held her sweaty body tight even as he felt her pussy contracting around his sensitive cock.

Tom couldn’t hold back anymore, and impaled Holly to the hilt, holding himself there. He didn’t have to wait long before his cock expanded slightly just as his seed burst forth, deep inside her. His cock twitched as her pussy milked him of every ounce of cum.

As their orgasms subsided, Tom collapsed on Holly, their sweat mingling, his hips still rutting slightly. Holly looked up at him with the content look of a pleased woman. But her eyes held a touch of fear. “Tom, did you… did you come… inside,” she asked quietly.

Tom nodded, and kissed her cheek. “Yes, my love. You were just too irresistible. I couldn’t help myself.”

Holly began to cry softly. “But Tom, it’s almost my time of the month. I might be… might be…”

Tom raised himself up slightly, and smiled down at her. She smiled nervously. “Well then, Holly, we’ll take care of it. I’ll take care of you both.”

Holly, still smiling nervously, said, “Do you mean that? Really?”

“Holly, my love, I’ll never leave.” His smile was filled with warmth.

Holly purred, tears of joy rolling down her face. “Oh, Tom!” She pulled him down and kissed him fiercely.

The moment subsided, and Holly looked up at her lover. “Well, since I didn’t wait, and you’re still here…” She smiled ily at Tom, and with lust in her voice, asked, “Why don’t we do it again?”

Tom smiled and took Holly in his arms. She smiled and wrapped her limbs around him, holding him tight. She would never let him go.

This Tom and Reluctant Holly

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