Ashleigh removed her fingers from Tom's asshole and reached for the butt plug. She carefully applied a liberal amount of K-Y Jelly to the length of the plug, then reached to caress Tom's ass with her left hand.
She moved the plug to the opening of his asshole, which was freshly lubricated from her fingers, and applied gently pressure. As the head of the plug began to enter Tom's ass, she reminded him to relax and not fight it. Tom began to moan as she applied more pressure. Then the head slipped into his asshole with a plop and Tom jumped.
"Easy, Tommy, that's the head. That's the biggest part. The rest of this is easy. Just relax and let me help you."
She let the head stay a moment so he could get used to the size, then began to apply pressure gently to slide the short shaft into his ass so the plug was fitted as nicely as hers. When the plug was firmly imbedded, she leaned forward and kissed his ass cheeks.
"It's completely in, Tommy, just relax and it will begin to feel better and better. Are you OK? I love you, Tommy, darling."
"I'm....OK...It's...just....very....different."
"Lie down on your side and get used to the feeling. Your cock is certainly reacting just fine. You're bigger than ever, Tommy, I can't wait for you to screw me with this big cock."
Tom rolled over on his side and smiled. He reached for Ashleigh and she came into his arms. She kissed him warmly, rubbing her breasts into his chest, toying with his cock between her warm thighs. It didn't take long for Ashleigh to generate a real need in Tom and she rolled him onto his back.
"Let me sit on you, Tommy, that way you don't have to move."
Ashleigh raised herself and spread her legs to straddle Tom. She felt her own butt plug move in her ass and knew she would very soon have both of her holes filled. She grabbed his cock with her left hand and positioned it at the entrance to her pussy. Closing her eyes to fully enjoy the sensation, she began to sink down over his really hard cock and moaned as he began to enter her.
"Oh, God, you're so big. I can feel both cocks inside me. Oh Tommy, it's wonderful. You are filling me up and moving my butt plug at the same time. Oh, you wonderful man."
Ashleigh continued to sink down, impaling herself on his hard spike until he was fully inside her. Tom felt the additional pressure of the butt plug but there was no pain or discomfort. He began to realize that his cock was fully inserted into her but it wasn't as hot as he imagined.
He found he could relax and let her use his cock without overheating himself. In this position, anyway, the butt plug was proving to be an asset. Ashleigh began to move her hips to please herself. Forward and back, left and right, around in circles, leaning forward to kiss Tom, then leaning back to reveal the base of his cock sticking out of her pussy. Tom massaged her breasts whenever they were in reach, pinching the nipples and grasping the fullness of them in his hands. Ashleigh moaned with growing excitement.
"Oh, yes, Tommy, play with my tits, rub them, pinch them, I love it, yes, yes, oh your cock feels so good, Oh I'm cummmmming."
Several times Ashleigh pushed herself to orgasm. Finally, she sat up straight, eyes closed, relaxing her breathing. Tom was still fondling her breasts and she placed her hands over his, pressing his hands into her flesh.
"Fuck me, Tommy, get on top or behind me and fuck me with this big cock of yours. Please, Tommy, I want to get fucked now."
Tom grasped her by the hips and rolled her over onto her back, keeping himself inside her through the move. She lifted her legs to circle his waist and locked her ankles behind him, wrapping her arms around his neck. Tom assumed the classic pushup position, resting his weight on his hands and his toes. He felt the butt plug in his ass as he began to pump his cock into Ashleigh's dripping wet pussy.
Tom marveled at the lack of sensation that seemed to engulf his cock due to the butt plug. It was as if his cock wasn't attached and he was just going thru the motions.
Suddenly the feelings returned in a rush and he felt the pressure to fill her pussy with his hot juices. He couldn't quite cum and he didn't want to hold back. The pressure became almost unbearable. Tom fucked Ashleigh as hard and as fast as he possible could, trying to empty his balls into her. Finally, he cock gushed his hot juices and his asshole tightened around the intruder causing double sensations in his groin.
Tom emptied his balls into Ashleigh's pulsating pussy and tried to compress the plug in his ass in the process. The sensations coupled together were overwhelming. Minutes after he finished pumping his juices into her, he still felt the continuing need to press forward caused by the constriction in his asshole. The feeling was intense but not painful. He found he really enjoyed the feeling generated by having the butt plug in his ass while he fucked Ashleigh.
As they rested, Tom realized the feeling of the butt plug was not the same as being fucked in the ass but maybe it was a step in that direction. He began to think that with Ashleigh's help he may someday experience something close to what she was feeling and have his curiosity satisfied.
For now, the butt plug was as far as he was willing to go but who knew what the future might bring. Whatever it was, he was certain that Ashleigh would have a lot to do with it. He leaned down and kissed her on the nose, causing her to open her mouth and search for his lips.
"So, what do you think? Was it nice? Did you like it? Shall we do it again? Talk to me, Tommy, I think it was delicious!"
"It was nice. It was interesting but not painful and yes, someday we should do it again. Thank you for pushing me to try it. It is a feeling I think I would like to experience again."
"Oh, that's good. We're going to experience lots of things, Tommy, just you wait and see. There's a whole world of experience just waiting for us. MMmmm, I can hardly wait."
When he finally removed his spent cock from her dripping pussy, Ashleigh convinced Tom to allow the butt plug to stay in place overnight. He had to have continuous pressure to remind his asshole that it had been enlarged so that next time the insertion would be easier.
After a lot of kisses and caresses, he finally agreed and they rolled together one final time before falling asleep.