"What?"
"It's just I don't like sleeping with a shirt on. Truth is your mother usually sleeps in the nude but tonight I will settle with just sleeping topless. Can you maybe help your mother pull her snug little tank top off of her . . . please baby."
Like she had to say please to such a request! "I . . . sure," he said trying to control his excitement. Was he really about to get a glimpse of those tits of hers!
His excitement died a quick death though when she added with a coy smile, "Of course, you better turn the light off first so you don't see anything you aren't supposed to, baby."
"Of course," he said, "I was planned on doing that anyways."
After reaching over and clicking off the light he found the room—much to his disappointment—to be utterly dark, leaving him no chance of catching even the smallest glimpse of her heavenly boobs.
"Here sit on the bed next to me, Jimmy," she whispered to him.
She found his hands in the dark and slowly guided them to the bottom edge of her tank top. The next three or four seconds might have been the most tantalizing of his young life as he slowly helped peel his mother's tight tank top off of her.
"Thanks baby," she said before tossing the top casually off into the dark somewhere. "That is much better."
"No problem," he said rising to his feet. He was about to walk away when she reached out and caught him by the hand. "Wait, aren't you forgetting something?"
"No . . . what?"
"How about a kiss good night. You know to celebrate our wonderful evening together."
"Sure," he said trying his best to sound casual. They rarely gave each other kisses anymore and when they did it was usually just a quick little peck on the cheek. He surmised because she was still a bit drunk and was more emotional than usual she wanted a kiss, but whatever the reason, he was happy to oblige her as he leaned down to give her the requested kiss.
The kiss turned out to be no simple affair. He was aiming for her cheek but in the dark somehow his lips found hers, in no small part thanks to her guiding hand. Their kiss lingered on a beat or two longer than was necessary before he managed, with a great effort, to break it off.
He wondered what, if any, reaction she might have to their kissing on the lips but all she did was let out a gentle sigh while snuggling under the covers—the darkness hiding the shameless smile on her face.
He was crossing the room and was about to exit when she called out, yet again. "Honey wait."
"What?" he said before sighing. He just couldn't seem to get out of her room.
After a brief pause she said softly, "I love you."
"I love you too Mom," he said before turning to leave. He was more than a little anxious to make good on his escape in order to get busy taking care of that fucking erection taking off her tank top had caused him to have. To this end he had just managed to step out of the room and was shutting the door when she called out to him again.
"And I love the way you have taken care of me tonight and I have another favor to ask . . ."
Lingering in the doorway he wondered: what possible favor could she be thinking of asking him?
"Oh, forgot it, never mind, you would never go for it."
"What?" he replied as he stepped back into her room curious. "Tell me."
"Well, it's just I had too much to drink tonight . . . kind of thanks to you and the room is spinning a bit. I was wondering maybe if you could come and crawl into your mom's bed next to me and just hold me until I fall asleep anyways."
Being stunned by the sheer audacity of her request, he lost his voice for a moment.
"I guess you probably think you are too old to hold your mother though huh," she told him in a voice resonating with sadness, "Sorry for even bringing it up. Just go to your own bed and forget I asked . . . your mom is being silly I suppose."
The marked sadness in her voice did it. He quickly moved toward the bed saying, "No, it's OK, I can lay down next to you for a few minutes and hold you until you fall asleep if that's what you really want."
"It is," she whispered. "But hey you need to get out of those jeans and take off that shirt. I know I haven't done your laundry in a while and your mom's sheets are freshly cleaned so . . ."
"OK sure," he said figuring it was dark anyways so she wouldn't be able to see the still somewhat pronounced tent pole sticking out from under his dark boxers.
After he hurriedly undressed he crawled into bed next to her. Alyssa was stretched out on side facing him and as soon as he got himself settled down she whispered, "I have changed my mind."
For a moment his heart sank; she didn't want him in her bed after all?
"Instead of you holding me, I want to hold you. It's been a long time since you let me cuddle you in my arms honey."
"OK . . . if that's what you want."
"It is. Now turn your back to me honey and just relax."
After turning over on his side with his back to her, he waited in breathless anticipation of being held by his "mommy".
He could fell her breath in his ear, tickling him, before she began to whisper, "Honey, your needy mommy just wants one more thing from her baby."
"What?"
"That kiss you gave me good night was so good it left my poor heart begging for another one. Please baby could you give your mommy just one more kiss good night before she passes out on you."
He sighed as he turned his head meaning once again to aim for a soft kiss on her cheek. She was having none of it. Using one finger she deftly steered their lips together.
They kissed softly, once, twice, their lips parting and coming together again. After the second kiss he tried to pull away but she murmured a single word that set his whole world on fire, "More."
Once more, their lips came together, delicately exploring, parting, only to come together again. They shared another three or four, he lost count, gloriously soft sweet kisses before she finally pulled back whispering, "Hmm, that was nice. We should make doing this a tradition."
He was afraid to ask. Make what a tradition? Sleeping together, him in his boxers only, her topless in a pair of sexy sleep shorts, or the kissing part? Or maybe, could he be so lucky, both!
Within less than a minute she was out like a light snoring softly next to him; her arms wrapped tight around him in a tight spooning position, her big tits squished nicely up against his back.
He laid there for a few minutes wondering if he could somehow extract himself from the bed, without waking her up, before finally giving up and succumbing to a restless sleep.
A few hours later, he woke up with a painful erection. At some point while sleeping he managed to roll out of her tight embrace. Sitting up, he rubbed his eyes while trying to figure out what to do about his morning wood. Glancing at the digital alarm clock on her nightstand he saw that it was morning; 4:07 to be exact.
He knew what needed to be done—retreat back to his own room and have a very hot whack off session while reliving taking off her tank top but this time with the lights on so he could see her glorious mounds of joy.
With this thought squarely in mind he was just starting to pull the sheet down as a prelude of getting out of the bed when she rolled over. Mumbling she reached out and touched him lightly on his arm, "Good you're still here."
He held his breath hoping she would quickly fall back to sleep but instead she began tugging on his arm. "Come on snuggle up next to your mom honey. She wants to be held."
Turning onto her side, she continued to pull softly on his arm. It seemed he had no choice. He carefully snuggled his body against her as they assumed a new spooning position with this time him holding her.
He tried to keep his lower body somewhat away from her, fearful she would feel his large erection poking against her backside, but she was not complying. "You are too far away hon," she whispered.
Reaching back she placed one hand on his hip pulling him forward as she pushed her lower body back. Mumbling softly she said, "Mmmm, that is better. Now you are snuggled up against your mother the way she likes."
He held his breath willing for his erection to die a quiet death but it was not working. Instead with her backside snuggled tight against his crotch his erection was growing even more powerful.
As her breathing slowed, and then became steady, indicating she went back to sleep he considered his alternatives. Escaping from her bed to flee to his own room in order to take care of business was seemingly out of the question considering the way she was snuggled against him.
On the other hand, willing his erection to die and pass gently into that good night was not working. Something had to give . . . but what?
When she sighed in her sleep and kind of jiggled her ass snuggling it tighter against him-- that is against his raging hard on-- the answer came in the form of his involuntary response: he simply could not help himself as started to slowly hump his mother's ass.
When she showed no signs of coming awake due to his soft humping, he became more emboldened. Knowing if he was going to do this it should be done quickly, Jimmy reached down and carefully managed to extract his rock hard seven and half inches from his boxers as he pulled it out of the fly in front.