Return To Pleasant Street Ch. 12

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Tim Dooley visits his pregnant ex-babysitter.
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Part 12 of the 14 part series

Updated 10/23/2022
Created 12/07/2003
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D.C. Roi
D.C. Roi
1,333 Followers

SURPRISE

Tim Dooley is another of my neighbors on Pleasant Street. Tim's only twenty and is attending the local community college. To save money, he's still living at home with his parents.

Tim works part time at a local restaurant, mainly nights, and he doesn't have class every day. He likes helping out around the house, and sometimes runs errands for his mother. As far as I know, he's not dating anybody right now.

Lori Jacobs also lives on Pleasant Street, with her husband Lincoln. Lori's pregnant and the other day at the market I happened to overhear her telling one of her friends that her husband seems to have lost interest in sex since she began to show.

Tim and Lori know each other. Actually, Lori used to baby sit for Tim back when she was a teenager.

Let's suppose that Tim has always had a crush on Lori. And let's suppose that fate somehow throws Tim and Lori together. What might happen?

OH MOMMA!

"Could you do me a favor and drop some stuff off at Lori Jacobs' house today?" Tim Dooley's mother asked the young man one morning.

"Sure," he replied. He'd be only happy to see Lori, who he'd always had a crush on, again. Actually, he'd had the hots for her ever since she used to be his baby-sitter, a long time ago. She was, in his opinion, one of the hottest girls he'd ever seen. She was very petite, but just the same, she had always had an incredible body, at least in Tim's opinion. She had starred in many of the young man's sexual fantasies over the years, but she was a lot older so he'd never even considered asking her out. When he learned she'd gotten married, he was depressed for days.

He knew she'd moved back to Pleasant Street after she and her new husband purchased her parents' home when her folks retired and moved to Arizona. He'd been meaning to drop by and welcome her to the neighborhood, but hadn't gotten around to it.

"The stuff I want you to take is in the living room," his mother continued. " It's your old crib, playpen, and a few other things like that. I'm positive your father and I won't need them any more."

"Baby things?" Tim thought. "Is Lori pregnant?" he asked, surprised that he felt a little twinge of disappointment. So much for a visit with his "sexy" former babysitter.

"I think she's almost seven months along," his mother informed him. "I thought I told you."

"If you did, I don't remember." Tim replied. So much for his sexual fantasies about his former baby sitter. "What time is she expecting me?"

"I told her you'd bring the stuff over this morning," his mother replied.

Since he did have the day off, Tim didn't mind taking the baby things over to his former baby sitter's house. He carried the items out to his car and stuffed them in the back seat. After he finished, he went back in the house and had breakfast. After his mother left for work, he headed for Lori's house.

Lori greeted him at the door wearing a pink sweat suit. The snug-fitting outfit did nothing to hide her obviously swollen belly. Tim was surprised to note that it didn't look as if she'd gained much weight anywhere else, though. The rest of her tidy little body looked a lot like he remembered it. Her dark hair, which she once wore long and straight and almost reached her waist, was now cut in a very short pixyish style that looked very good on her. It actually made her look younger, Tim thought. And, even though it was fairly early in the morning, she looked as if she was wearing makeup. Obviously the Lori wasn't letting the fact that she was pregnant give her an excuse to let herself go.

"Hi, Timmy," she said, "How have you been? It's been ages since I've seen you. Your Mom said you'd bring over some baby things today. I understand you're in college now."

"Um...I have the stuff Mom sent over," Tim replied. He lifted the folded porta-crib to show her. "This is some of it. There's more in the car."

"Put it over there," Lori said. She gestured toward a corner of the kitchen.

Tim set the porta-crib and high chair he had been holding down where she indicated, then he went out and got the remaining items and set them down next to the first ones. "There, you won't have to buy a crib, porta-crib, high chair, or changing table now," he said.

"Thanks so much for bringing those things over," Lori said. "Everyone's been so nice. What with buying the house, money's kind of tight. It sure helps that we won't have to buy some of the expensive baby items."

"From what I've seen, it happens every time a woman gets pregnant the first time," Tim said. "Most of that stuff was mine."

"No kidding!" Lori looked surprised. "Oh, I'm not being a very good hostess. Would you like a cup of coffee, Timmy?" She paused, grinned, and chuckled. "You are old enough to drink coffee now, aren't you?"

"Yeah, I'm old enough," Tim said. He liked the fact that she was teasing with him. "I'd love a cup of coffee."

"I have a pot on," Lori said. "It's out in the kitchen. She started for the kitchen.

Tim followed her to the kitchen. As he did, he noticed that her bottom, which he'd always thought was one of the better ones he'd seen, looked just as good as it always had, if not even better. Her buttocks moved wonderfully under the soft material of her sweat suit as she walked ahead of him.

"Watch it, there," Tim cautioned himself. "You shouldn't be having those kinds of ideas about a pregnant lady." But even though he tried, he couldn't stop having exactly those kinds of thoughts.

Lori and her husband had a nice house, neatly kept, with modern furnishings. The kitchen was large and had a breakfast bar. Tim sat on one of the stools. Lori poured two cups of coffee and set them in front of them. "Do you take cream or sugar?" she asked.

"Black."

"Me, too." She climbed up on the stool next to his.

"You cut your hair," Tim said.

"Yeah, I hated to do it, but it was a real pain having to deal with that long hair and being pregnant," Lori replied. "I may let it grow again once I have the baby, I'm not sure."

"I like the short haircut," Tim said.

Lori smiled at him. "Do you?"

He felt himself blushing as he nodded.

"So you're at community college?" she asked.

"Yep, in my second year," Tim replied.

"What are you studying?"

"I'm getting my associate's degree in English," he said. "I've been offered a partial scholarship in a teaching program after I graduate."

Lori giggled softly. "I have a hard time picturing you as a teacher," she chuckled. "I remember you as the bratty kid I used to baby-sit for."

"Was I really that bratty?" Tim asked.

Lori laughed. "No, not really. Actually, you were a pretty good kid," she said. "You didn't give me half as much trouble as some of the kids I sat for." She shook her head. "That seems like another world, though. Seems like just a little while ago I was your sitter, now here I am, pregnant, and you're all grown up and in college."

"Time marches on," Tim said. "Although I'm not that sure I'm all grown up yet."

"Sometimes time marches," Lori snorted. "But sometimes it crawls."

Her comment puzzled Tim. "What do you mean?" he asked.

"You've never been pregnant," she replied. She laughed. "And I guess you never will be, huh, being a guy and all. This has been the longest six and a half months of my life."

"Isn't the pregnancy going well?" Tim asked.

She shrugged. "It's normal, I guess. The doctor says everything's fine and the baby is healthy."

"You scared?"

She nodded. "I sure am."

Tim patted her on the shoulder. "No problem. You'll do fine."

"That's easy for you to say," Lori retorted. "You don't have to go through having your body get all gross and disgusting. After this one, I'm not having any more kids. No way. This one's already messed up my life enough."

Tim didn't think her body was gross and disgusting at all. "Oh?" he said, interested in her comment. "How is that?"

She sipped her coffee and nodded. "My husband, Link, was all excited about my being pregnant...until I started to show. Then, all of a sudden, he's 'sleepy' or 'tired' or something every time I hint at wanting to make love. He hardly ever hugs me or kisses me any more and he told me he thought I should be wearing pajamas to bed!" She stared into her cup, then looked up at him. He could see the tears that had welled up in her eyes. "I'm sorry, I shouldn't be bugging you with my problems."

"That's OK," Tim said. "I don't mind." He took a sip of his coffee and smiled at her. "You know, I think you look great...hot, really." The minute the words were out of his mouth, he thought, "What the hell did I say that for?"

"You're kidding!" Lori looked amazed. "How...how can you say that? I mean, my body's so...so yukky."

Tim shook his head. "I don't think so," he said. "I think you're even prettier now that you're pregnant."

"Timmy Dooley, what's gotten into you?" Lori asked. "I don't remember you being like this when I used to baby sit for you." She grinned and shook her head. "I wish my husband felt the way you do about how I look." She patted her belly. "I know you're trying to be nice, but I'm a realist. I see myself in the mirror. I guess I can't blame him."

"You look good to me," Tim said without thinking. "You always have." The minute the words left his mouth, he felt his face getting warm.

Lori stared at him with a surprised look on her pretty face. "I...I do? You really mean that?"

Tim nodded. "I sure do," he said, "there's something about a woman who's regnant, a kind of glow..."

"Yeah, sure," she snorted. "You can say that, but you don't mean..."

Just like that, she was crying. Tim had never been comfortable around crying women and wasn't sure what to do. He did know that sometimes a hug helps, so that's what he did. He slid his arm around his former baby-sitter and leaned forward a little. "You'll be ok, you really will," he said softly. "And I did mean what I said about you being prettier now than you were before you got pregnant. I think you're the prettiest woman I know."

Lori leaned toward him as his arm went around her, and put her head on his shoulder. She let him hold her as she cried. It surprised Tim to feel his penis stiffening in his jeans when she pressed against him.

"Th...thanks, Tim," she stammered into his shoulder, "I...I needed that. God! It's been so long since I've had a hug."

She went to straighten up, went off balance, and almost slipped off the stool. Trying to support herself, she wound up with a hand between the young man's legs, brushing against his stiffening organ. He pushed her back up onto the stool, but her hand didn't seem to want to lose contact with what it had found.

"You...you..." Lori gazed at him wide-eyed.

Tim wasn't sure what to say, so he kissed her. He wasn't sure what she'd do about that, but he couldn't stop himself. He didn't seem to have a lot of impulse control.

Lori moaned softly and returned his kiss with far more passion than he expected. Her slender arms slid around his neck and her swollen belly pressed against him, amplifying his excitement. He thrust his tongue between her lips and it was met by hers. Her arms tightened around his neck and her tongue lashed his.

He slid his hands under her sweatshirt, cupped her breasts, and rubbed his thumbs over her erect nipples. His action brought impassioned moans from her. Her breasts were hard and felt swollen.

"What...what are we going to do?" she gasped when the kiss finally ended.

Tim didn't respond. Instead, he managed to get her bra undone and once he did, his hands cupped her hot, smooth flesh, and his thumbs resumed their caress of her rock-hard nipples. Lori's mouth fell open and her head rolled on her shoulders.

"Oh! Oh, Timmy! Oh, God, Timmy!" she groaned, her hands pressing his against her. "Yes! Oh, yes!"

Tim had never made love to a before in his life and was a bit nervous. He was pretty sure there wasn't much chance of harming the baby, but wasn't sure how to get Lori her from the kitchen to a place more appropriate for making love.

Lori solved the problem for him. She slid off the stool, holding his hands against her breasts, and looked up at him. "Let's go to the bedroom! Please!" she moaned. "Please! Don't give me time to think!"

Tim knew where the master bedroom was and it didn't take long to get there. Once inside, he stripped Lori's sweatshirt off, then pressed her back until she was sitting on the bed.

"I...I'm not...pretty...this...way..." she murmured, "I..."

Tim silenced her with a kiss. "You're gorgeous," he said after the second kiss ended. At the same time, his hands worked her sweatpants and panties down over her swollen belly.

"How...how can you...you...stand...to...to look at me?" she whispered. She buried her face in the crook of his shoulder.

"Like I said, I think you're gorgeous," Tim said and meant it. "I always have." He'd often fantasized what she'd look like naked, and had actually seen her in pretty scanty bikinis a time or two, but he found the way she looked now incredibly exciting. She had gained a little weight, but only in her belly which was stretched tight and had blue veins showing against her pale skin. Faint stretch marks were evident, too.

Lori's breasts were swollen, too. Bluish stretch marks showed on their pale surfaces. Her nipples, surpassingly large, protruded from the rounded masses they capped.

Tim leaned forward, drew a rigid nub between his lips and began suckling, like a baby. Lori moaned and clutched his head. "Oh! Oh, God, Timmy! So Long! It's been so long! That feels so good!"

"How could her husband not want to do this?" Tim wondered while he sucked her distended nipples and lashed them with his tongue. Not only were they wonderful to look at, they were incredibly sensitive, too! While he tantalized her breasts with his lips, his hands slid gently over the rest of her body.

He got a surprise when the baby inside her moved and one of its appendages pressed against his seeking hand. Surprisingly, contact with the baby inside Lori added to his desire. Over her belly, through her pubic hair, his hand moved, seeking her vagina, wanting to add to the thrills he was giving her.

"Uh!" Lori grunted when his finger contacted her labia. "Oh!" she gasped and her hips thrust upward when his fingers contacted the swollen bud of her clit. "That feels so good! Ah! Ah! Ah!"

She was soaking wet! Tim couldn't imagine why her husband didn't want to make love to her! She was so lovely and so responsive! His fingers slid through her swampy opening, then he thrust one finger into her. His thumb rubbed her clit while his digit probed her insides.

"Yes! Oh, yes! Yes!" Lori cried, her hips twisting and turning wildly. "Yes!"

Tim abandoned her breasts and began kissing the tightly stretched skin covering her distended belly. Once again, he experienced contact with the baby inside her when it kicked against his exploring lips. All the while, his finger continued to thrust into her and his thumb kept rubbing her swollen clit. Lori was going wild.

"Yes! Oh, yes! More! More!" she cried. "I love it! So long! So long! It's been so long!"

As Tim kissed his way down over her swollen belly, Lori realized what the young man planned to do. Her hips arched upward, off the bed. "Yes! Eat me, Timmy! Give me your tongue! Give me your tongue!"

His tongue replaced his thumb on her clit and she exploded. "Wah! Yes! I'm...oh, God, Timmy...I'm coming! I'm coming! Oh-oh-oh-oh-oh-oh-uh-uh-uh-uh!"

Tim, with his face buried between Lori's legs, could feel how frantically her hips were twisting, thrusting, and squirming. "How long has it been since her husband made love to her?" he wondered. Obviously quite a long time, given the power of her orgasm! His erection jumped and stiffened, trying to tear its way out of his jeans. He wanted her! He wanted her bad!

He began to shed his clothes while he continued working her over with his fingers and tongue. It seemed to take a long time before her orgasm was complete, but eventually the wild spasms shaking her body began to calm and she lay still on the bed, her chest heaving, staring at him.

"My God, Timmy! That was so incredible!" she gasped. "Oh, God! I needed that so much!" She watched while Tim finished taking his clothes off. When he was naked, he stretched out next to her on the bed and she was in his arms, kissing him while his erection pressed against her distended abdomen.

"I want more, Timmy!" she exclaimed between kisses. "I don't care! I want more! I need more! What you did, that just took the edge off!"

Tim's erection, trapped between their bellies, felt movement as the baby once more shifted inside her. It was unbelievably thrilling to the young man!

Tim had every intention of giving her what she wanted. Actually, he was so turned on he couldn't have stopped if he'd wanted to, but he sure as heck didn't want to stop and, obviously, neither did Lori. He intended to give her as much as she could handle. The only thing he was worried about was that he was quite a bit bigger than Lori. He didn't think the missionary position would be a good idea. But there are other ways to make love.

"Roll over, so your back's to me," he said.

"OK." Lori turned, then snuggled back against him, her firm bottom caressing his erection. "Oh, Timmy, I like this!" she cooed. "I like having you against me like that!" She moaned softly as he slid an arm over her and cupped a bloated breast, tweaking the nipple. "Yes! Oh, God, Timmy, yes!" she crooned. She moved her hips and his swollen organ probed between her firm wonderfully shaped buttocks.

Tim slid his hand down her leg, pulled it back over his, then he pressed the tip of his erect penis against her wet labia. He shifted his hips a little, and his engorged shaft began to enter her.

"Oh!" she groaned. "That's it, baby! I want you! Put it in me, Timmy!" Her hand pushed his aside and her hips moved, trying to get more of him into her. He could feel her fingers pushing at his erection, trying to stuff it inside her! She really did need this!

He pushed his erection deeper and deeper into her surprisingly snug opening, feeling her warmth engulf him and the rippling walls caress him. Ripples of delight went up his back. He struggled to hold back, to slide into her slowly, so he could savor the fantastic sensations.

"Oh, God, Timmy!" she murmured. "It feels so good to have you me! I needed this so bad!"

"How...long...has...has... it... been?" he grunted. Waves of ecstasy washed over him. This was far more exciting than he ever dreamed it would be.

"Too damn long!" she replied. She began rocking her hips and his erection slid easily in and out of her snug slit. "Way too damn long!"

Tim was more aroused than he could ever remember being. He needed to come! He gripped her hips and drove into her, shaking her petite body. It did occur to him that the baby probably had no idea what was happening, but that thought faded as passion engulfed him.

"Oh, God, Lori...I...can't...I can't wait!" he groaned. "I'm too close! I'm gonna come! Oh, Jesus, am I ever!"

"Come, baby!" Lori crooned. "I want to feel you come! Please!" Her hips began moving with increasing urgency.

Tim couldn't hold back any longer. Like and uncoiling spring, his insides unwound, spewing what felt like an endless supply of his hot cream. "Ah, yeah! Take it!" he cried, as spasms of wonder wracked his body.

"I can feel it! Oh, God, I can feel you coming! It's so hot!" Lori cried as his spend splattered her insides. Her body quivered. "Yes! Oh, yes, Timmy! I...I'm...oh, God...I'm coming! Again! I'm coming again! Yes! Yes!" Her tidy bottom squirmed against Tim, milking all of the joy she could get out of him, wringing every last bit of pleasure possible from their passionate connection.

Her wild motions eventually calmed, then stopped, and they laid there, pressed together spoon fashion, with Tim's half-hard erection still in Lori, savoring the aftermath of their wild encounter.

D.C. Roi
D.C. Roi
1,333 Followers
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