Learning To Swing Both Ways Ch. 04

"Your panties are very wet Jill. Would you like me to take your panties off you?" he teased her.

Jill nodded and gasped, "Yes, please take my panties off."

Aaron eased her panties down over her buttocks, past her thighs and then let them slide to her ankles. Jill stepped out of them and he put them on his desk. He returned to fondling her ass and thighs and he soon had her squirming with desire. Jill moved her body as if she were trying to get Aaron's hand near her pussy so he slid it between her legs and stroked the outer lips of her labia. Jill squirmed under the touch an emitted a soft groan. He started to push Jill's skirt up but she stopped him and then she took it off. It was a wrap around mini and she had it off in an instant. She looked so sexy standing there leaning forward slightly over his desk. Her cute ass was framed by her thigh high hose and her short blouse ending at her waist line. She actually looked hotter by keeping the blouse on.

Aaron ran my hands all over Jill's ass, thighs and pubes feeling her wet pussy. He slipped his finger into her vagina and then added a second one. He took some lotion from his desk and he pushed a finger between the cheeks or her ass and massaged into her nether hole. Then he fingered Jill's ass and pussy at the same time. She was going wild with the double penetration and cried out to him.

"That's it finger me, play with me. Make me cum, please make me cum," Jill pleaded.

Aaron continued to work her ass and pussy and within minutes she had her first orgasm. Jill held onto the desk with both hands as her body jerked and spasmed with her climax. He worked his fingers in and out of her holes as she clenched and relaxed her vaginal and anal muscles tightening herself on the digits. He pulled his fingers from her holes and he stood up behind her. Aaron dropped his pants and boxers to his ankles and brought his rock hard cock to her buttocks. He let it rest against the hot flesh of her ass and he leaned over and whispered in her ear.

"Where do you want it first today? Do you want it in your ass or do you want me to fuck your pussy first?" he teased her and then licked her ear.

"Fuck my pussy first and then my ass. I want you to cum in my ass," Jill murmured.

Aaron then eased his cock into her pussy and fucked her from behind until she had another orgasm. Then he moved his cock to her ass and fucked her for a short time before he unloaded his semen in her anal canal. Jill looked so hot leaning over the desk with his cock sliding in and out of her asshole that he just couldn't prolong my ejaculation any longer. He leaned over her and she milked his cock dry until it softened and popped out of her ass.

Their sexual encounters in the office usually ended up the same way, with Aaron cumming in Jill's ass but only after she had cum herself two or three times. Jill would surprise him from time to time. One day she leaned over the desk and as he ran his hands up her legs he discovered that she had already removed her panties. Another time she just walked in without her skirt and panties looking very hot in just her hose and blouse. Once she brought one of the dildos with her and put it in her pussy so that when Aaron took off her panties he would find it. Jill liked being fucked in the ass and having her pussy filled with the fake cock.

Jill eventually moved in with Aaron and they had morning sex before they left his condo. On the way home from the office Jill would remove her panties and Aaron played with her pussy. Once they reached the condo they were both very hot and they went inside and fucked like rabbits. Jill had really adapted to anal sex and Aaron came in her ass at least once a day. She still loved the anal toys as well especially the beads. Jill picked up a unique dildo that had two cock heads on a handle. It looked like a big letter Y. Jill would put one cock in her pussy and the other in her ass for double penetration. Sometimes they would be in a 69 position and she would suck Aaron's cock as he double fucked her with the dildo. Jill went wild and juiced all over the fake cock as Aaron filled her mouth with cum. There seemed to be no end to her creativity and willingness to try new things although she had no interest in bringing other sex partners into their relationship.

TWO YEARS LATER

Jill received a great job offer and it made sense for her to take it. Aaron and Jill continued to live together but Aaron needed a new assistant. He decided to call Mack to see if he knew of anyone. Mack suggested that Aaron could have one of his lady boys.

"That won't work Mack. I'm living with Jill and she wouldn't want someone as pretty as Tola or Mali in my office," Aaron responded.

"Hey no problem they can just dress like young men. They ask about you all the time anyway. It would be a good way for them to earn some money in addition to the allowance I give them," Mack suggested.

"That could work, as long as they looked like young men. Which one do you suggest I hire," Aaron asked.

"Hire them both but you only have to pay them what you would pay one assistant. Hey I just thought of something. Hire them as husband and wife and then Jill won't suspect anything," Mack offered.

"That's a great idea," Aaron replied and then asked, "When can they start?"

"Tomorrow if you want, they don't drive so they will be taking public transportation," Mack advised.

"Tomorrow is great. I can also pick them up and drop them off on certain days," Aaron added.

"Consider it done," Mack said concluding the conversation.

Aaron hung up the phone and he was excited about having Tola and Mali work for him. He thought of all the possibilities with those two beautiful ladyboys. Aaron had missed them since Jill had moved in with him but now he could renew his action with those two hotties. Things had slowed down with Jill as they do in most relationships so Aaron should have plenty of energy for the ladyboys. Life was good!