Ashleigh woke up and looked at the clock. 5am. Suddenly the thought struck her that she was at the wrong house. Not that she didn't like being here in Tom's bed with him sleeping beside her but her work clothes were across town at her own apartment. She slipped quietly from the bed and went into the bathroom, closing the door behind her. After her shower, as she just finished drying herself, the door opened and Tom entered completely naked.
"Good morning, princess." He said, "You're up early today."
"Good morning, Tommy," she replied, as she stepped toward him.
She reached out with her right hand to grasp his hardening cock and, wrapping her left arm around his neck, kissing him deeply.
"I have to get across town to change before work this morning." she said, as she released him. "I didn't bring any work clothes with me."
She left the bathroom and began to pack. Tom completed his morning ablutions and returned to the bedroom still naked.
When he entered, Ashleigh had her bag packed but she was also still naked. He noticed she held her panties and a small dildo in her hand as he approached.
"Tommy, will you do me a big favor? I'd like you to put this butt plug in my ass, please, but no funny stuff because I do have to go to work."
"Of course, princess, but why do you want this thing in you if you're going to work?"
"Sharon mentioned that the day may come when you would like to fuck my ass and if I wasn't ready it would really hurt instead of feeling really great. She suggested that wearing the butt plug for a few days would adjust my ass so it would be ready for you. Was she right, Tommy? Would you like to fuck my ass?"
"Absolutely, princess, you've got a great ass and I'm sure it would be a great pleasure to fuck it."
Tom closed the distance between them and kissed her gently.
Wrapping his arms around her, pressing his cock to her wet pussy, he increased the pressure of his lips and was rewarded with her tongue in his mouth. After several seconds of delicious kissing, Ashleigh broke away.
"I said no funny stuff, Mr. Tom, I'm late already. Now, will you help me with this thing or should I do it myself?"
"Get up on the bed, I'll do it."
Ashleigh reached down and slipped her panties over her ankles, then turned and knelt on the bed with her ass high in the air. Tom retrieved the K-Y Jelly and used his finger to spread some on and in her asshole. Ashleigh wiggled her ass at his touch. He then covered the butt plug with the jelly and placed the head at her opening.
"Are you ready?"
"Yes, Tommy, just do it slowly please."
He pressed the plug forward against the resistance of her sphincter. Almost immediately her sphincter relaxed and the head popped inside her asshole. Tom paused as she groaned and waited for her to indicate that he should proceed. When she nodded to him, he pressed the remaining length of the plug into her and patted her ass lightly.
Ashleigh rolled to her side, then to her back, taking deep breaths in the process. Resting on her back for a moment, she smiled widely at Tom, who was looking a little concerned. She folded her legs up and pulled her panties up to her hips, raising her hips to complete the process, then sat up and turned to drape her legs over the side of the bed. With a deep breath, she lifted herself to a standing position, wiggled her ass a little to adjust the plug, then smiled at Tom and walked easily to him.
"See", she said, "It's really not bad once it's in. During the day it just stays there and I notice it a little when I move around, but it feels nice. Thank you, kind sir."
She kissed him lightly, stepped past him and continued to dress.
Tom began his dressing with a grin on his face than couldn't have been erased with dynamite. A few minutes later, Ashleigh was ready to leave.
"When can I see you again, Ashleigh," Tom asked, "Is Wednesday night ok? If you like, we could go to dinner and a show or something."
"That would be great, Tom, call me when you get a chance and we can talk about it. I really have to go now or I'll be late for work. Bye, honey, talk to you soon."
Ashleigh kissed him warmly, then walked out of the room, overnight bag in hand. Tom heard the front door close and continued with his own morning routine.
As Ashleigh drove away from Tom's house, she was grinning from ear to ear. She had been thoroughly fucked by both Tom and Sharon this past week, had a butt plug in her asshole as she drove, and Tom was anxiously looking forward to seeing her again. It was a wonderful morning.
It was a busy Monday morning at work. Ashleigh was being asked to do a variety of things in addition to her reception duties. Every once in a while the butt plug would remind her it was still there and she smiled to herself. About 11am, the phone rang for the umpteenth time.
"Carter Industries, Ashleigh speaking, may I help you."
"Hi, Ashleigh, this is Sharon. How are you doing?"
"I'm fantastic, Sharon, how are you?"
"Never better, sweetie, how did things go with you and Tom after we dropped you off last night?"
"Oh Sharon, I can't talk now, I'm at the front desk. Can you call me at home tonight? I really need to talk to you. By the way, I'm wearing your little friend and it is getting very comfortable."
"You mean the butt plug? Why you little devil you. Did you put it in at Tom's?"
"No, HE put it in me this morning before I left."
"My God, Ashleigh, you are a bold one. I will definitely call you tonight. We have to talk!!!! Bye for now."
The rest of the day flew by and suddenly it was 5pm and time to leave.
When the phone rang at 7:30 that evening, Ashleigh answered it on the second ring. She was expecting to hear Sharon's voice so she was surprised to hear Tom's. After a little small talk, he asked how her asshole was managing to which she replied that it was doing quite nicely. They discussed the coming tennis outing on the next weekend and she mentioned that Sharon had given her some lessons and she was quite ready to participate. Finally, he asked if she would have dinner with him on Wednesday at his house. When she agreed, he suggested she bring a change of clothes so she could spend the night and go directly to work the next morning. Ashleigh agreed to his requests and stated she would arrive about 6pm. Moments after hanging up with Tom, the phone rang again and it was Sharon.
Sharon immediately began asking questions about Ashleigh's evening with Tom and the morning insertion of the butt plug. Ashleigh repeated the events of the evening and the morning in complete detail, along with a discourse on her feelings. Sharon was quite pleased with the events and with Ashleigh's reactions to them.
Sharon then recounted her own evening with Ted, in detail, including the discussion about sex between the men.
She went to great lengths to impress upon Ashleigh that Ted's reactions, while verbally conservative, were dramatically different between his legs as his cock grew extremely hard while he was introduced to the idea of being sucked and fondled by a man.
"I think he secretly would like to experience having sex with another man and is afraid to let anyone know about it. How do you think Tom would feel about the idea?"
"I don't really know but I think I can find out on Wednesday. I'm having dinner at his house Wednesday night and he asked me to bring a change of clothes so I can stay overnight. That should give me a good opportunity to find out more about his ideas regarding sex. Where are you going with this, Sharon, it sounds to me like you have some kind of plan in mind."
"Not really, Ashleigh, but I was thinking that if we four got together for an evening and it turned sexual, it would be much more fun if the boys could participate as much as we could. I know, for instance, that they would both enjoy watching us make love to each other and I don't think they would mind making love to us in the same room, even switching partners, but I don't think they are ready for touching each other yet."
"You're probably right about that."
"What we need to do is to find some easy way for them to get some experience, in complete privacy of course. Is this something you'd be interested in? I'm not jumping the gun here, am I?"