Ashleigh's Adventures Bk. 2 Ch. 03

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Ashleigh begins to train Tom's ass.
4k words
4.59
21.5k
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Part 13 of the 34 part series

Updated 10/31/2022
Created 10/25/2005
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Ashleigh was extremely busy at work on Wednesday. About 11am she looked up and saw Tom striding towards her. He was grinning from ear to ear. When he reached her desk he bent forward and kissed her lightly.

"Good morning, Ashleigh, you look really great this morning."

"Good morning, Tommy, thank you. I feel really great. Mr. Davis is expecting you. He said you should go to the shop whenever you get here. Here's your visitors badge, just sign the book, please."

"Yes, ma'am, whatever you say ma'am. Can we do lunch, ma'am?"

"Yes of course, kind sir, but not before 12:30 today, OK?"

"That's fine, princess, I'll pick you up out front."

In a moment he was gone, the door to the plant swinging shut behind him, and Ashleigh was left with the memory of his smile and wet panties.

Ashleigh walked quickly to the waiting convertible and slid in, moving straight across the seat to kiss Tom warmly. He returned her kiss, wrapping his arms around her, then gently pushed her back into her seat so he could drive to the restaurant. He drove directly to the freeway rest stop they had previously visited and they sat in the shade of a tree with their lunches. Tom told her of his recent meetings and the prospects of future business while they ate.

When they finished, during a slight lull in the conversation, Ashleigh took the initiative.

"Tommy, I know you like to fuck and you are great in bed, but have you ever really thought about the possible variations in the sex act?"

"I have to admit, princess, I think about it all the time when I'm not working. What kinds of things are you talking about?"

"Nothing in particular, I'm just curious about your views on the subject. I'm sure there are things you think you would like to try but haven't had the opportunity. There are also things you probably think you wouldn't like to try because you don't think they would bring you pleasure or because somebody told you they were nasty or something like that. What are your views about sex in general?"

"Hmmmm, I never really thought about it like that before. I suppose there are sexual activities that I don't particularly care to participate in but I'm not sure I could list them without some time to think about it. How soon do you want an answer?"

"Ahha, hedging your bets, I see. Actually, I'm not in any rush on that subject. We can talk about this more tonight. Anyway, my lunchtime is over and I have to get back."

Tom reached out and pulled her to him, kissing her passionately. Ashleigh melted as his hot lips burned a savage image of lust on her heart. In mere seconds, her panties were wet and she was thrusting her tongue into his mouth. They were both gulping for breath when they broke the kiss, and Tom very gently helped her to stand up. This time he held her close and kissed her ear. Ashleigh circled her arms around his neck and held him tightly.

Tom stopped the car at the entrance to the plant and turned off the engine. He leaned over toward Ashleigh, putting his right hand behind her head, and drew her to him. He kissed her gently and lightly massaged the back of her neck. Ashleigh murmured her delight at his touch and his kiss.

"Thank you for lunch, kind sir, but now I must go slay my dragons. I'll see you about 6 or so tonight."

"I'll be waiting, princess, have a lovely afternoon."

Ashleigh floated into the building. Inside there was chaos so her reverie was immediately interrupted with the demands of her job. By quitting time, she was eager to get away. She raced home and, after removing and carefully washing the butt plug, showered quickly. She then packed an overnight bag with work clothes for tomorrow and hurried out to her car for the cross- town drive to Tom's.

Ashleigh let herself into Tom's house with the key he gave her and found him in the kitchen. She put her bag down and moved to circle him in her arms. They kissed warmly, rubbing their bodies against each other.

"Good evening, princess, welcome home."

"Good evening, Tommy, what a nice way to be welcomed."

They kissed again, languidly, Tom's hands stroking her back and moving to cup her ass cheeks. His tongue was dancing in her mouth and she replied in kind. After a few minutes of serious kissing and fondling, Tom pushed her away slightly.

"I have dinner almost ready, princess, but it's up to you. It's just spaghetti so it can simmer for awhile if you'd rather wait. We can have a glass of wine and talk or something and eat later, or we can eat now and talk later. What would you like to do?"

"I'm starving, Tommy, I'd rather eat now -it smells heavenly. We can talk while we eat and get to the or something later, OK?"

"Sounds good to me. Put your things in the bedroom and freshen up if you like, I'll have dinner served in about 5 minutes."

Ashleigh kissed him quickly, then danced out of his way to retrieve her bag and take it to the master bedroom. She hung up her work clothes and decided to change as well.

When she returned to the kitchen, she was wearing Tom's blue dress shirt, unbuttoned to the navel, and her thong bikini panties, along with an impish grin.

"Wow. How am I supposed to concentrate on dinner with you looking so hot?"

"Just relax, Tommy, you know you'll win the prize. I think it's just more fun to tease for awhile, don't you?"

"It sure is. I haven't had this much fun in quite a while. I mean, except for recently with you."

"Don't blush, Tommy, I understand. Now, is there anything I can do to help with dinner?"

"No, I think we're quite ready. If you'd like to have a seat I'll bring the spaghetti over. You could pour the wine if you like, it's already opened."

After tasting his spaghetti and verbalizing her approval, Ashleigh began the subject she really wanted to discuss.

"Tommy, have you thought about our lunch discussion at all?"

"Well, only a little, I've been pretty busy this afternoon. I must admit you have captured my imagination with your questions, however. What exactly is it that you want to know? A list of my likes and dislikes about sexual behavior or what?"

"Well, something like that, but what I really wanted to know about was your attitude. After all, attitude is everything. Did you know that the greatest sex organ you have is between your ears? Think about it. When you decide you don't like something even before you try it, you will not like it. If you also decide that you love something even before you try it, you will love it, am I right?"

"Yeah, I guess so. I never thought about it like that but it sound reasonable."

"OK, so your greatest sex organ is in your mind. I know men are mostly visual so you therefore use your imagination a lot, right?"

"Right."

"So, when you imagine getting your cock sucked, how do you visualize it? I mean, do you visualize a particular person sucking you off or it is just a nameless, faceless person generating these great feelings in your cock?"

"Hmmm. Interesting question. Usually, before you came along, I would probably visualize almost anyone - probably the face of the girl in the magazine I was reading at the time but no one in particular. I visualize you now because I have had the experience but that is only recently."

"Could you get the same feeling if you visualized another man sucking your cock?"

Tom's eyes glazed over and Ashleigh held her breath. She was concerned that she had gone too far too fast and it seemed like forever before he answered her.

"Actually, I probably could, given that my mind is my greatest sex organ. When you think about it, a mouth is a mouth and the person it is attached to is kind of incidental. By the way, are you related to Ted? He asks these same kind of questions all the time - makes you wonder!"

"What do you mean, Ted asks these same kinds of questions all the time."

"Oh, don't get me wrong, not about sex, but Ted is always asking why not. It's a character trait that probably makes him as good as he is in the lab. He is always stretching your imagination to help solve a problem."

Ashleigh breathed a huge sigh of relief. Tom's admiration for Ted was evident in the statement and that made it a little easier for her to pursue the subject. Now that she knew Tom was open minded about sex, or so he said, she could explore just how open he was to the new ideas that she and Sharon were about to propose. She let the subject drop for the moment and suggested they clean up the dinner dishes.

After dinner they sat on the couch and sipped wine. Ashleigh again broached the subject of Tom's imagination in regard to sex.

"What kinds of things do you think you would like someone to do to you?" she asked.

"Well, let's see, apart from the obvious, I like to be touched almost everywhere. I'm not particularly ticklish so any part of my body would feel good, provided I was comfortable with the person doing the touching."

"Remember your greatest sex organ." She reminded. "It can overcome a lot of perceived problems, you know."

"Yeah, I guess you're right. If I knew there wasn't any danger, I mean, like a threat of future retaliation or something, then I suppose I could like being touched by almost anyone."

"Even if it was another man?"

"Well, yes, if I was in the right mood. I know, I know, my greatest sex organ. I guess I'll need some practice but if it is someone I know and trust, I could probably handle it."

"Someone like Ted, for instance?"

"Well, yeah, someone like Ted. He is a nice guy and I like him. Besides, I already trust him with my living. If he doesn't come thru for me in the lab I don't make any money. I never thought of Ted as being gay, if that's what you're hinting."

"No, absolutely not, Ted is not gay. He is a sensitive guy who may be open to expanded sexual activity, however. Sharon thinks he would like to experience some sexual contact with another man as a part of widening his sexual horizons and she asked if I would see if you would be willing to go along with the idea."

"Are you serious? Ted wants to have sex with me?"

"No, darling, he doesn't want to have sex with you, not yet anyway. Sharon has been noticing that he needs to expand his sexual horizons and she is looking for a safe way to do that for him. I suggested that we might engage in a foursome of some sort but that might mean that you and Ted would have the opportunity to become intimate with each other. Sharon and I have already become intimate, if you haven't guessed, and we were wondering if you boys would like the same kind of experience. You see if we work it the right way, we could all enjoy each other. What do you think?"

"Are you suggesting that I have sex with Sharon and Ted?"

"Not both of them at once, unless you really get horny, but yes, in a way, I am. You see, Sharon and I were talking about having a private party with some games. The games of course would be somewhat sexual and that led to the question of whether or not you and Ted would be willing to take the chance of having sexual contact - or even outright sex - with each other during the course of the evening."

"Say, for instance, that we play strip poker and Sharon loses. If she loses the next hand when she has no more clothes to lose, she will have to perform some personal service for the winner. If the winner was you or Ted, no problem. If the winner was me, also no problem, agreed?"

"Yes, I'm following you, go on."

"Change the scene and suppose that you are the first one naked. Then you lose the next hand and you are to perform some personal service on the winner. Again, if the winner is me or Sharon, no problem. What if the winner is Ted?"

"What would you be willing or not willing to do with Ted in that instance? You see, we are not talking about love here, just sex. Would you rub his back? Would you kiss him on the mouth? Would you suck his cock? Would you fuck him in the ass? Would you allow him to suck your cock or fuck you in the ass? Do you see the consequences? We don't know what your limits are, if any, and we don't know Ted's limits either."

"Wow, that's quite a leap from ordinary sex. I suppose, in a way, it's not really that far fetched. After all, it would be in the context of a game and I wouldn't have to say I love him. Boy, I don't know. When you think about it logically, touching another human being is just that - touching another human being. In that sense, it could be pleasurable if you let it, right? I mean regardless if it was a man or a woman doing the touching."

"On the other hand, I've been brought up like most other men to be macho and to think exclusively about women as the objects of my sexual desires. I'm not gay and I prefer women but I don't know how I would react if Ted - or any man - was being really intimate with me. Wow, - that's quite a challenge."

Ashleigh was sitting quietly during his monologue, allowing him to convince himself that he could handle it and perhaps even get some enjoyment from it. Finally, she spoke up.

"Let's go into the bedroom and try something, I promise it won't hurt."

"Ok, but you haven't arranged for Ted to jump out of my closet or anything, have you?"

"No, darling, it will be just us but I want you to exercise that imagination of yours just a little and let's see what happens."

Ashleigh took his hand and led the way to the bedroom. She instructed him to strip and lie on his back with his eyes closed. She also stripped so he could see that she was naked. When he was positioned in the center of the bed, she began with his toes, rubbing his feet and ankles and sucking on his toes. With each new move, she asked if he liked it and Tom replied in the affirmative. Some things he liked better than others but overall it was very pleasurable. Ashleigh noticed his cock growing harder as time passed.

She rubbed his lower body with both hands. When she reached his cock she grabbed it in one hand and Tom groaned. She began to rub his cock and play with his balls in the other hand. As she did so, Tom was moaning louder with each stroke. Then she suggested to him that these were Ted's hands massaging him. She was amazed that his cock grew even harder at the suggestion.

Without saying another word, she placed her mouth over the head of his cock and swirled her tongue around it. Tom moaned even louder as her actions took him to the edge of orgasm. Ashleigh removed her mouth and pinched his cock just behind the head to prevent him from coming at the moment. She asked him whose mouth was just on his cock and he didn't answer.

"That's right, Tommy, it could have been anybody's mouth on your cock and it would feel just as good, wouldn't it? It really doesn't matter if it's me or Sharon or Ted or somebody else who is sucking your cock as long as it gives you pleasure, you're happy, right, darling?"

"Yes, yes, please suck it some more, whoever your are, it feels great."

"That's my Tommy, open your imagination to the world of sex. It can be so much more interesting if you let it."

She leaned forward and kissed his nipples, taking each one into her mouth gently and applying slight pressure. Tom groaned his appreciation. She moved up his body with little kisses, ending with her mouth on his and her tongue inside it. After a few minutes, she broke the kiss and instructed him to roll over.

When he was positioned on his stomach, she began again at his feet and elicited more groans. When she reached his ass, she instructed him to raise up onto his knees. After he did, she leaned forward and kissed his ass cheeks, stroking them with her hands at the same time.

Finally she grasped his cheeks in her hands and spread them apart, baring his asshole. She leaned down and licked it and Tom groaned loudly. Upon questioning, he revealed that his asshole seemed to be really sensitive and he loved having her tongue on it or in it.

Ashleigh leaned over to the bedside table and retrieved the K-Y Jelly. Placing a small amount on her finger, she easily covered his asshole inside and out while Tom moved and groaned at her actions.

With a command to stay put, she got off the bed and went to her overnight bag. She returned with the butt plug in her hand and covered it with the jelly. She kissed and licked his ass cheeks as she prepared to invade his asshole. Finally, she placed the head of the dildo at the entrance to his asshole.

"What are you doing?" he demanded.

"Hush, baby, this is just the little butt plug that I wear. I promise, you'll love it."

She pushed the plug forward and Tom groaned as his sphincter resisted. On her whispered orders to relax, Tom finally allowed the plug to pass into him with a pop. She let it stay while he got used to having the intruder in his formerly virgin asshole. Tom groaned the whole time but his cock got harder and bigger than ever. Ashleigh reached between his legs and began pumping his cock with her left hand as she pushed the butt plug forward with her right hand.

When it was completely inside him, she instructed him to roll over and lay on his back. When he completed the maneuver, his cock stood straight up as hard as a steel bar and he was grinning even with his eyes closed.

"Thank you, Tommy, you've been such a good sport. Here is your reward."

Ashleigh said as she straddled him with her hand on the hard tool. She placed the head of his cock at the entrance to her dripping pussy and began to sit down, impaling herself on his hard spike. She moaned loudly as each inch of his hard cock entered her until their pubic hairs were meshed together.

Ashleigh began rocking herself back and forth on Tom's hard cock, moving her hips in slow circles at the same time. She took his hands and placed them on her breasts. Tom immediately covered her breasts, then moved to grasp her hard nipples between his thumb and forefinger. As he twisted her nipples, Ashleigh cried out for him to pinch them harder.

"Pinch them, Tommy, pinch them hard. Yes, that's it, harder, oh Tommy harder, help me cum. Oh God, Oh Yes, Yes, Yes, that's it."

Ashleigh stiffened and her hot cum splashed over Tom's hard cock as the first of her orgasms hit her. She rested momentarily then began another series of movements that resulted in another orgasm. She drove herself to cum several times before the heat of her cunt and the heat of her cumming became too much for Tom. With one loud groan, he blew his hot cum deep into her pulsating pussy, his cum blasting into her in streams that lasted a long,long time.

Even after he came, Tom's cock remained hard for her to use for more orgasms of her own. In a fog of afterglow, Tom realized that the butt plug in his ass had caused him to have a more intense orgasm than he had ever had before and it also allowed him to remain hard for Ashleigh to continue her orgasms. He was secretly very delighted with this beautiful lady and vowed to do whatever she asked of him.

Finally exhausted, Ashleigh fell forward, resting on Tom's chest. He kissed her tenderly and encircled her with his arms, his cock still inside her dripping pussy. A few minutes later, Ashleigh raised her head and kissed him warmly.

"Oh Tommy, that was fantastic. Thank you, my darling, thank you."

"I should be thanking you, princess. I never had such a good time and stayed hard for as long as I did tonight. Your idea about the greatest sex organ really works. I don't have a great imagination like you do so I'll make you a deal. I'll go along with whatever you want in regard to sex so long as nobody gets hurt and everybody agrees. This idea sure turned out great."

"That's a deal, darling, and I promise you won't be disappointed. I won't guarantee you'll really like everything but if you at least try we will all have a great time. Now I think we need to get some sleep, tomorrow is a workday, you know. Would you like me to remove the plug or do you want to do it?"

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