Stranded in Heels Pt. 05

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Sarah gives Doug the moon
3.2k words
4.88
2.2k
8

Part 5 of the 5 part series

Updated 05/01/2024
Created 03/23/2024
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Doug smiled and pulled his jersey over his head and dropped it in the floor. He pushed his boxers down his legs and stepped out of them. His 7" cock jutted from his slightly hairy midsection. He crawled onto the bed and took Sarah into his arms.

Again they kissed passionately. Sarah ran her hands over his body, feeling his skin. She put her hands on his chest and rubbed and pinched his nipples. Doug put a hand on her bare ass cheek and pulled the crotch of her panties against his throbbing shaft. They both moaned when he pushed against her, rubbing his hard cock against the small hard cock confined by her panties.

Sarah reached down and gripped his shaft. He moaned and his hips jerked when he felt her soft hand wrap around his dick. He moved his mouth to the side of her neck and her ear when she started to move her hand up and down his shaft. 'Was this how they would do it?' he wondered. 'Would she jack him off while they kissed?' He'd been thinking about this moment ever since he walked in and saw her in her panties earlier this morning.

Sarah kissed Doug's neck and the top of his chest. She started to move her body down, trailing licks across his chest until she got to his nipples. Doug inhaled sharply when she first ran her flat tongue across his nipple, then took it in her mouth and bit down gently. His nipples got hard and his hips rocked up to meet her hand.

She continued to move slowly down his body, toying with his sparse dark hairs with her tongue as she moved closer and closer to his middle. Doug had rolled onto his back and now had his legs spread in anticipation of her getting between them to take his cock into her mouth. He put his hands on the sides of her head as she ran her wet tongue around his balls and up and down his hard shaft.

Sarah put her hands on the insides of his thighs and pushed her head low, licking his balls, inhaling his sexy musky man-scent. She ran her flat tongue up and down the big vein on the underside of his hard shaft. Doug moaned and pumped his hips up against her. She wrapped her slender fingers around the shaft and pulled it out from is body. She tilted her head to look at him.

"Look at me, Doug," she whispered. He raised his head to look at her. She put the flat of her tongue against his cock just under the helmet head, then, still holding his gaze, tilted her head and took the head into her mouth. She slowly pushed her face down, taking more and more of him into her mouth. Doug moaned. His hands tightened on the sides of her head. His hips jerked.

Sarah pumped her head up and down on his cock, savoring his taste and smell, trying to decide if she wanted him to cum in her mouth or her ass. When she felt his dick throbbing in her mouth and knew he was getting close she made her decision. She pulled her head back and let his mushroom head slip from her lips. She kept her fingers wrapped around the pulsing shaft as she moved back up on top of him.

When her face was over his she flattened her body out on his, her chest against his chest, her torso touching his, her soft legs laying against his hairy legs. Her panty covered cock was pressing directly on his thick shaft. She lowered her mouth to his to kiss him. Doug opened his mouth to accept her tongue and push his against her. He pushed his hard cock up against her, and she humped hers down against him.

She slid to the side to lay face down on the bed next to him. She turned her head to face him. "I want you on top of me," she whispered hotly. "I want to feel your body on me while you take me."

As Doug rolled over on top of her she reached down to pull the thong to the side. Doug knelt between her legs. He gripped his shaft and rubbed his bulbous head up and down her ass crack. He felt her flinch when the tip of his cock rubbed against her puckered hole. He felt her push back against him, trying to force his dick into her.

"Push easy," she whispered as she pushed back against him. She felt Doug's head start to spread her tender hole. She moaned and spread her legs a little wider and tilted her pelvis to give him a better angle.

Doug felt her start to open for him. A shiver ran through his body when he realized what he was about to do. He'd never even tried to have anal sex with a woman. He tried to hold back, to resist the urge to jam his hard cock into her. A few times his hips jerked and he pushed harder than he meant to, and he heard her yip as if in pain, but when he started to pull back she stopped him. "Please don't stop," she whimpered. "Please fuck me," she said.

So Doug pushed. They both let out a sharp 'OH!' when his big head popped past her tight sphincter ring. Doug sensed that he needed to stop for a bit to let Sarah get used to it. When he felt her push back against him he started to push again. His dick slid steadily into her until his balls lay against hers and she could feel his curly pubic hair in her upper ass crack.

"Mmmm, yes, that's it!" Sarah sighed. She pushed back against him. "Lay down on me," she said softly. "I need to feel you laying on me while you're in me."

Doug lay down on her back. He kissed and licked her neck and ear, then lay his face sideways on hers as he started to work his hips to fuck his throbbing shaft in and out of her. His breath came in soft grunts as he pulled almost all the way out and then pushed all the way back in.

"Oh, yes, yes, that's it, baby!" Sarah moaned. She reached back and put her right hand on his thigh. She curled her left arm to put her hand on his face. She caressed his face while he rocked in and out of her.

Doug worked one of his hands under her and found her hard nipple. Sarah moaned when she felt him pinch her nipples while he slowly fucked her. She felt the pleasure start to build deep inside her. She felt her muscles start to flex and pulse around Doug's throbbing shaft. She felt his shaft throb even harder.

Doug pushed deep into her and groaned. "Oh, shit, Sarah, you feel so good!" he said as his cock erupted, spraying hot cum deep in her bowels. He held his dick deep in her, jerking to push it deeper, as spurt after spurt of his cum exploded into her.

"Ohhh, yes, yes, yes, yes!" Sarah squealed when she felt him hold his throbbing cock deep inside her. She knew he was coating her inner walls with his cream. She could almost feel the hot liquid filling her.

Then the felt her own little cock erupt and fill the panty liner in her panties with her own creamy cum. She felt a series of spasms, more than usual, and wondered if her cum was leaking out to make a mess on Doug's soft comforter.

When both of their spasms finally ended Doug collapsed on top of Sarah, laying heavy on her back, gasping for breath. They both moaned when he rolled off of her and his dick slipped out of her now sloppy hole. Doug lay on his side and worked his arm under her to pull her to him. When she looked at him he pulled her mouth to his and kissed her.

"That was incredible!" he whispered. "Thank you."

Sarah smiled at him. "For me, too. Thank you." She pushed her lips against his again, then rolled over to get out of bed. "I'll get a towel and clean you up," she said.

When she went into the bathroom she got some toilet paper and wiped the inside of her feminine pad and panties, then her ass crack. She sat down on the toilet and pushed more of his cum out of her, then got more toilet paper and laid it in her crack to be held in place by her pink thong.

She got a warm damp cloth and a hand towel and went back to the bedroom. She gently, lovingly wiped Doug's cock and balls and around his belly and thighs with the damp cloth, then dried him with the towel. She tossed the rag and towel back through the bathroom door and lay down next to Doug. He put his arm around her shoulders and let her snuggle into the crook of his arm with her head on his chest.

"How are you feeling right now?" she asked softly.

"I'm not totally sure," he said honestly.

"Do you regret it?" she asked.

Doug lay there for a minute, then squeezed her shoulders. "Not even a little bit."

"That was your first time? With a woman like me, I mean."

Doug nodded. "I hope I did it right," he laughed.

"Oh, honey, you did just fine," she said.

"So, um, do I need to do something... you know, for you?" he asked "One time when I was younger and Dani was talking to me about sex she said I should always make sure the woman had pleasure, too."

Sarah put her arm over his chest. "No, honey, you don't need to do anything for me," she laughed. "You already did it."

He raised his head to look at her. "So you, while I was... while we were..."

Sarah laughed and nodded her head on his chest. "Yes, baby, when you were blowing your huge load inside me I was making a big mess in my panties."

"Wow!" Doug said. "I didn't even realize you were touching yourself!"

Sarah laughed. "I wasn't. What you were doing felt so good that I got off with you. It doesn't always happen, but it's really good when it does." She rubbed her hand on his chest. "But even if that doesn't happen, pleasing you like that makes me feel so womanly that I'd be okay if I didn't get off. It's worth it to me to please you."

Doug squeezed her shoulders again. "Sarah, it's been a long day and I'm very tired. I really do need to check on the animals now, and then go to bed."

"Okay, baby," she said, rolling off of his arm.

He sat up on his elbow and looked down at her. "When I come back in to go to bed I wouldn't be mad if you were in there waiting for me," he said softly.

Sarah looked up at him and smiled. "I love the idea of sleeping in your bed with you," she said. "But I'm not ready for that yet. And I'm not sure you are, either. Right now we have this nice afterglow thing going on, but that will wear off by morning and you might feel different."

"And you wouldn't?" he asked.

She shook her head. "This isn't my first time, and I've spent the night with a man before." She giggled. "Sorry to burst your bubble, but I'm not an innocent little virgin."

Doug laughed. "I knew that," he said. "But what's that got to do with me feeling different in the morning and you not?"

She shrugged. "I'm not sure. I just don't want to rush you," she smiled. "What we have now could be special. I don't want to ruin it. Besides, I'm not ready for you to see me without a wig and make-up, and I'm not sure you're ready for that, either!"

Doug laughed and rolled out of the bed. "Ok. Good enough. But if you change your mind..."

"Thank you, sweetie. I'll see you in the morning."

When Doug left the room Annie came in. Sarah just realized that all three of the dogs had stayed in the living room while she and Doug were having sex. Sarah sat on the edge of the bed in her sleep bra and panties. Annie came to her and put her head in her lap. Sarah used both hand to rub and scratch Annie's head.

"Oh, Annie," she whispered. "What have I done?"

When she went to her suitcase for a gown to sleep in she saw Doug's t-shirt and put it on instead. She put her wig on the Styrofoam head and snuggled under the heavy blankets.

Sarah was again in the kitchen starting to cook breakfast when Doug came back in from caring for the animals. This time she didn't worry if the shirt pulled up to show her panties. Or since she was still wearing the thong, her bare ass cheeks.

"Good morning," Doug said when he came in. He took his coveralls off and walked to the breakfast bar. "There you are teasing me again."

Sarah laughed as she poured coffee in a cup for him. "What makes you think I'm teasing?" she said coyly as she put the cup down in front of him.

Doug reached out and ran his hand over her bare cheeks under the t-shirt. "I know you're not," he said huskily. "So, now you have your girly gowns and you still chose to sleep in my t-shirt?"

Sarah looked at him and blushed. "Yeah," she said. "It felt cozy."

She went back to her breakfast preparations. "So I was looking at the weather on my phone and it looks like it might start to thaw out today."

Doug nodded. "Yep. They reopened the turnpike this morning. It's still pretty slow and dangerous, though."

She nodded. "I saw that. I'll just have to wait and see, I guess."

Doug nodded. "There's no sense in you taking chances," he said. It was almost as if they both were hoping the weather wouldn't improve enough for her to leave. It seemed like it had been much longer than just two nights she had been at his house.

"Hey, after my shower this morning how about you give me a tour of the barn and introduce me to your animals?" she asked as she put the plates on the table.

Doug nodded. "We can do that."

"Um, Doug?" Sarah asked. He looked up at her. "Are we okay? I mean, after..."

Doug smiled. "As far as I'm concerned we're good," he told her. He paused for a moment. "When I was coming back in from the barn just now I wasn't sure how I was going to feel when I saw you this morning," he admitted. "But I'm fine. I hope you are."

Sarah smiled and nodded. "I'm fine. So, let me get these dishes cleaned up and I'll go jump in the shower."

While she was at the sink Doug walked up behind her. He pressed his body against hers and reached around to rub her chest and belly. "You wouldn't happen to want some company in that shower, would you?" he asked, kissing her on the neck.

Sarah stood still and let him kiss her neck, then twisted around to face him. She put her arms around his neck and looked into his eyes. "Doug, really look forward to sharing a shower with you," she said softly. "But not yet. I'm not ready yet."

Doug smiled and gave her a peck on the lips. "Okay," he said. "I can wait."

Sarah hugged him. "Thank you."

Doug stepped away from her. "I've got a couple of things I need to do in the barn," he said. "After your shower you can walk on over there if you want. Will that be okay?"

"Sure thing, sweetie," she smiled. "I'll be over there in a bit."

"Wear Dani's boots to the barn," he told her, grinning. "They're easy to clean."

Sarah looked at herself in the full length mirror. She liked the look. She was glad she'd worn a pair of jeans for the drive to Danielle's cabin last Thursday. She didn't need to fluff them... they fit tight enough that she didn't have to worry about wrinkles. She turned and looked at her butt, and liked what she saw. She hoped Doug would like it, too.

She put another pair of spandex thong panties on, again with a feminine pad in the front triangle. Then she put on a fresh pair of black pantyhose. She didn't really know why, but she had a feeling that Doug had a thing for feet in pantyhose.

She pushed her feet into Dani's boots and headed for the barn.

She found Doug working on a piece of equipment she recognized... she'd seen the football team at school use one. It was a big four-wheeler with a small pick-up bed on it. This one also had a big rack on the front.

"Hey," she said when she walked into the barn.

Doug looked up and smiled. "Hey. Hang on just a sec and let me get this put back together."

"You get it all fixed up?" she asked.

"Just tinkering with it," he said. "I'm going to be increasing my herd this spring and summer so I'll be using it a lot."

Sarah sat down on a big wooden bucket. "I talked to my principal before I came over here," she told him.

"Oh?" Doug said.

Sarah nodded. "She said the roads there are still pretty bad. They've already cancelled school for the rest of the week."

Doug nodded. "Nice. At least for the kids."

Sarah nodded. "Teachers are back on Thursday and Friday for the meetings we were supposed to have today and tomorrow," she told him.

"Okay," Doug said. He was wondering where she was going with this. He looked up at her. "So, are you trying to tell me you're leaving this afternoon?"

She shrugged. "From what I've seen on the news the turnpike is in pretty good shape."

"When do you have to be back?" he asked. "For work, I mean."

"I really need to be at work Wednesday morning to get ready for Thursday morning," she told him.

He stood up and took wiped his hands. He reached out and pulled her to her feet. "Will you stay one more night with me?" he asked quietly.

Sarah smiled and nodded. "I'd love to."

"I want you to sleep with me," he told her.

She took a deep breath. "That would mean letting you see me without my wig and make-up."

Doug pulled her to him for a kiss. "Good. It's time you let me see the real Sarah. I think I'll like her."

Sarah put her arms around his neck. "I hope so," she said as she let him push his lips against hers.

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AeneaTAeneaT7 days ago

I’ve loved this story, it’s told so sensitively and realistically. I think Sarah doesn’t have to be described as CD like at the beginning, just a pre-transition trans woman. But Doug’s sensitivity is so warm and loving, I wish I could find that for myself. Please keep going.

SexySenior56SexySenior5610 days ago

Too short! You’re such a tease!

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