Doug slept surprisingly well. He wasn’t sure he would, but once Jasmine snuggled up against him, it felt like the most natural thing in the world. During the night Jasmine had turned away and Doug rolled with her and woke pressed against her back. He felt his ‘morning wood’ pressed against her ass but didn’t want to move, even though his bladder was what woke him up. He also didn’t realize Jasmine was awake and simply liked the feel of his hard cock against her.
When she realized Doug was awake, she pushed against him in a stretch, grinding her ass against him. She felt his hand on her hip pulling her even tighter. She thought for a minute about what she had planned and decided to put off the asking for a little morning fun. It had been a while since she woke up with a handsome man who she actually liked.
With one hand she reached to the nightstand where she kept her clutch, retrieving a small foil pack and turning to face Doug. She reached down and held his cock, enjoying the hardness. She didn’t say anything but showed him the condom. He looked hesitant and glanced toward the hotel room’s bathroom. She smiled and nodded, getting up with him.
He was surprised when she went into the bathroom with him, his cock leading the way. When they got in there, she held him and aimed him at the toilet. He was hard, so it actually took a while. It was another new experience. Once done, she cleaned his tip with a square of tissue and stood in his place. She liked that he was quick on the uptake as he held her while she took care of business. He also cleaned her.
They both went to the single vanity and sink to brush their teeth and the two of them started jostling for position in front of the mirror. It was playful and they kept sliding their bodies against each other. By the time they were finished, they were both hard and very turned on. Without a word, they went back to bed.
She laid him on his back and unwrapped the condom and spoke for the first time. “Normally I would do this with my mouth, but this is a lubricated condom, and to be honest, I hate the taste. The first time I tried that, it was really awful.” She made a face that had Doug laughing. She unrolled the condom on him, the reservoir tip flopped over, which always made her smile. She stroked his cock a few times, then straddled him.
He watched with very little expression as she took his cock, pointed it straight up and settled down on him. When she felt him touch her, she aligned it carefully, and, moving very slowly, she felt his cock pop into her, right past her sphincter. She paused there and looked down at Doug. His hands were on her thighs as his gaze was between them with his head angled so he could see her cock.
Slowly she pushed herself down until he was completely inside her. She squeezed her muscles a bit and let him adjust to the feeling. She saw his face slowly change.
“Holy fuck!”
Jasmine smiled at both the expression and the look on his face. She felt that Doug wasn’t normally one to curse, but she also knew that unless he was in the habit of fucking virgins, he had never been in anything as tight as her ass. She lifted up and sank back down. She saw his eyes close and felt him push up toward her.
She moved very slowly, relishing both the feel of him and the honest look on his face. There was no guile, no secret agenda of the many guys who secretly wanted a transsexual, but his face was almost boyish in its lack of complexity. He was simply enjoying it and after several strokes, he looked up in Jasmine’s eyes. She was smiling down at him as she slowly rode him. She pushed down and stayed there, using her muscles on him as she took her own cock in her hand and started stroking herself to hardness.
Doug didn’t say anything else, he wasn’t sure what to say or do. His cock felt like it was encased in a velvet glove, he could feel her in ways he had never felt a vagina, not even his wife the first time they had sex. He paused in thought, it was the first time in hours he had thought of his wife and then he got distracted as she rose up and down again to get his attention when she felt he was wavering mentally.
Doug caught her eye again, she was upright and looked so incredibly beautiful that her cock actually seemed incongruous. It didn’t fit the image in some ways and yet in others, it fit absolutely perfectly. He thought about last night when he tasted it and when he felt it inside of him and recalling all that combined with this morning made him close his eyes briefly as he arched his back and pushed up deeper into her.
Jasmine saw his eyes close and then open again. His look had changed, she could tell he was feeling everything and was really enjoying it. She was as well. Yes, she worked part-time as an escort and had sex with most of her clients, but she rarely enjoyed it like this. Doug was the first one she ever slept with, and by that, she meant actual sleep. She had a few clients pay for the entire night, but she never slept, never let her guard down. Doug was something new for her and she decided to enjoy it for the both of them.
Her cock was hard, so she leaned down and took his hands from her thighs and put them on her breasts. She knew they weren’t overly large and she never wanted surgery, but her breasts were sensitive and when she felt his fingers tighten on her nipples, she hissed in appreciation. Doug was starting to get into it, even the newness of this wasn’t stopping him from doing what came naturally for a man with a woman.
He wrapped his arms around her and pulled her down against him. His cock stayed inside her, just barely. Then he kissed her! They had kissed last night, and while the kisses were good, there was a nervousness that made them feel slightly awkward, even in the elevator after dinner. Any sign of that was gone. Doug was kissing her as a lover. His tongue slid into her mouth and she started sucking on it like it was a cock. She felt him slip out and reached down to put him back in. Then she sat up and took her own cock in her hand, stroking it firmly.
She kept his cock buried within her as she stroked and looked down on him. “I love a cock in my ass!” She said smiling at him.
He was transfixed by her, her body moved sinuously without lifting off his cock, her hand moving quickly. Then, like last night, she spit on her cock. A move that would seem to feel wrong but fit so perfectly. Doug looked as her cock glistened while she stroked it.
“I’m going to cum on your chest again.”
Doug knew she wasn’t asking permission, just telling him what was about to happen, and he was looking forward to it. He watched as her cock seemed to grow, the small head expanded and darkening. He saw her hand seemed to blur on her cock. She was squeezing it so hard and brushing the glans with the edge of her thumb. With a small exhalation, she started cumming. It flowed onto his belly rather than shooting to his chest. It looked a bright white that also coated her hand as she kept stroking her slowly softening cock. Then she bent down and kissed him, trapping her cum between them.
“Now fuck me, please.”
Without a pause, he flipped them over. He knelt between her legs looking down at her with a look she rarely really saw, passion. He lifted her legs and when she held them up, he took his cock and pushed it against her ass, it popped back in easily. He started fucking her steadily, not quickly, but firmly. He grasped her calves to keep them elevated and looked at his cock going in and out of her. Her own cock was still gooey and there were strands of cum connecting them that were slowly settling down on Jasmine.
He started moving faster. She wanted to slow him down a little, but he felt so good! Now it was her turn to close her eyes and push her head back. She grunted as he pushed into her deeply.
Doug saw it and heard her noises, it really thrilled him. This whole trip was a fantasy come true, but it was so much more than that. His fantasy paled beside the reality. He started going faster, there was no way to stop or slow down. She was so tight, so hot, and seeing her react just sent him to the edge. He started climbing what he always thought of like a ladder. He can’t remember climbing so quickly or as high as ever before.
She felt him harden even more and knew he wouldn’t last much longer. He pushed deep and his whole body went stiff as he started to cum. It felt like being struck by lightning.
He felt wonderful as he pushed in as hard as he could and she could feel him cum into the condom and for a second wished he was bare so she could really feel it. It lasted only moments but felt much longer. Then he fell on top of her. As she held him, she could feel his racing heart and labored breathing. She loved that tiny period of time when someone was totally unguarded and vulnerable, so she just held him as he still felt so perfect within her. She felt him come back to himself.
They laid together both recovering as Jasmine thought about how to ask him for what she wanted.
