When Tom entered the bedroom he found a nude Ashleigh lying on the bed with her arms stretched above her head and her legs spread wide apart. Her eyes were closed as he entered but opened when he sat on the edge of the bed.
"OK, princess, I'll try this idea of yours but you have to take it really slow. Just to get started, how about we watch some of my sexy movies? I haven't seen any of them for awhile so it will be something different."
"Oh, Tommy, what a wonderful idea. You get naked and get the video set up and I'll put on my dildo and have the K-Y Jelly handy for later. Mmmmm, what a delicious idea."
Tom stripped off his remaining clothes and walked into the closet to retrieve the X-rated videos he had there. At the same time, Ashleigh retrieved her double dildo and began spreading some K-Y Jelly on the part that would be inserted into herself, just in case. When she spread her legs and placed the head of the dildo at the entrance to her pussy, her fingers told her the jelly was completely unnecessary.
The dildo slipped into her dripping pussy with ease and she sat up at once to complete her preparations. Standing by the side of the bed, she buckled the strap tightly around her waist allowing the other half of the dildo to stick straight out in front of her.
She then applied a liberal amount of K-Y Jelly to the dildo and brought the jar with her as she walked into the living room where Tom was inserting the first tape into the tape player. He had already closed the blinds and dimmed the lights so all was ready for their new activities.
Tom chose a tape that showed some ass fucking scenes, although the participants were guys fucking girls. The attitude of the parties was catching as Tom and Ashleigh lay side by side on the blanket Tom had spread over the carpet.
Ashleigh carefully ran her hands over Tom buttocks and thru the slit between them, touching his asshole only lightly with her fingertips. At each touch, Tom's ass moved as if to invite a deeper insertion of her finger. She rubbed her finger tips in the jelly and began smoothing it onto his asshole. Tom spread his legs in an attempt to give her easier access while still concentrating on the screen in front of him.
As the action on the screen heated up, Ashleigh began to push more and more of her finger into Tom's asshole. She had one finger completely inside him, then began to add a second finger. Tom reacted with a loud sigh to the second finger being inserted and Ashleigh carefully slowed down the process. Finally, she had two fingers deep into his asshole and stopped her motions.
"How does that feel, Tommy, is it OK so far?"
"It's a little strange, princess. I can feel your fingers moving inside me and that's something I never thought I would feel but otherwise it's OK. My ass seems to have expanded enough to handle the width of your fingers so it's just uncomfortable but not painful. At least not now."
"Good. That's what it should feel like. Now, get up on your hands and knees and I'll keep my fingers inside you while you change positions. Go ahead, Tommy, get up."
Tom raised his shoulders by doing a partial pushup with his arms, then backed into a kneeling position. Ashleigh was kneeling herself so she could move her arm at the same time as Tom moved his ass. When he was in position, she leaned forward and whispered quietly to him.
"Tommy, I'm going to start moving my fingers in and out of your asshole to simulate fucking. I'll stop whenever you say but I think you have to get used to my fingers before we put the dildo in. Are you ready? Oh, my, your cock is certainly ready, it's huge."
"Yes, I guess I'm as ready as I'll ever be. I can watch what's happening on the screen at the same time as you finger fucking me. Go ahead but start slowly, please. It still feels very strange."
Ashleigh began to move her greased fingers in and out of his asshole, remembering to brush his thighs with her breasts and stroke his cock with her other hand. Tom began to moan but didn't otherwise stop her activity.
She speeded up her thrusts and Tom moaned again, this time asking her to slow down a little. After a few more strokes, Ashleigh removed her fingers from his asshole and moved to a kneeling position behind him.
Her pussy was dripping wet and she couldn't stand the sexual tension any longer. With each movement of her body, her internal dildo was sending waves of emotion throughout her body and she needed to be really fucked. She positioned the head of the dildo at the entrance to Tom's asshole and pressed forward slightly. Tom took a breath and held it. Ashleigh immediately told him to relax as best he could.
"Don't tense up, Tommy, that will make it hurt for sure. You just have to relax and let your body handle the changes for you."
She pressed her hips forward again and the head of the dildo breached his asshole. As his sphincter was already expanded from her fingers, the head of the dildo slipped in almost easily, causing very little pain in the process. Ashleigh continued her pressing and soon the length of the dildo was entering Tom's no longer virgin asshole. When her thighs met the backs of his thighs, she announced that she was completely inside him and that he should relax for a few moments.
Tom took several long, deep breaths as these new feelings overtook him. He felt the fullness of the dildo inside his asshole and the softness of Ashleigh's thighs against his own and his brain was confused. They had switched places this time and the realization of that fact numbed his brain. He watched as the girl on the screen took a huge cock up her ass and seemed to glory in the act. Then the guy began fucking the girl with his large cock and she seemed to really enjoy the experience.
Tom groaned as the large cock on the screen slammed into the asshole of the beautiful, young girl. Ashleigh noted his reaction and began to pull back in preparation for her first fuck as "the man". She pulled the dildo out of Tom's asshole slowly, almost to the head, then began slowly pushing it back into him until it was fully inserted as deeply as it had been.
"Oh, yes, that feels great. Oh, Ashleigh, no wonder you like to be fucked in the ass. It's terrific. Fuck me, baby, like the movie guy is doing, fuck me good but still slowly."
"Ohmygod, Tommy, do you really want to get fucked hard?"
"Yes, I think so. I want to feel that thing going in and out of my ass. It's such a great feeling. Let's try a few strokes at least, please?"
"Your wish is my command, master, here we go."
Ashleigh began pulling back again and loved the feeling inside herself as well as the feeling she was obviously delivering to Tom. She shoved the dildo forward hard, slapping her thighs against his and forcing the dildo deep into her own pussy at the same time. Both Tom and Ashleigh wailed at the same moment. Tom straightened his back and bent forward to better accommodate Ashleigh's angle of attack. This change of angle forced the dildo deeper into his ass as well as deeper into Ashleigh's pussy.
Tom was pushing back as she pushed forward. Somehow he realized that he was delivering extreme pleasure to her as well as to himself and it seemed like it could go on forever. After a time, Ashleigh grew tired and the speed of her thrusts diminished. She was coming with almost every other insertion and her body couldn't keep it up.
Tom's cock was near the bursting point. Finally, as Ashleigh slowed down, his cock exploded. The blanket below him was covered with his hot cum and Ashleigh leaned over onto his back in complete exhaustion. Ever so slowly, she began pulling her dildo out of Tom's asshole. When she was completely out of him, she laid back on the floor with her eyes closed.
Tom turned around and laid next to her, reaching out to hold her in his arms. He kissed her breast and licked the taut nipple, then moved up to kiss her cheek and finally her mouth. Ashleigh barely had the strength to return his kiss but managed to wrap her arms around his neck as she did so. They lay in a close embrace, not speaking for a long time.
