Learning To Swing Both Ways Ch. 04

Aaron returned to the pool and thanked Mack for a wonderful time. Mack nodded and reminded Aaron of the need to be discreet about the new relationship. Mali and Tola smiled and waved goodbye as if they were two little nymphs. Aaron left the property and then drove home. He thought about Mack's contact in San Francisco and wondered how it would work getting his own ladyboy. Aaron figured that it would be an expensive proposition. He dismissed it as he thought about his sex life. He had Edna in the office and he had no trouble getting dates on the weekend. A ladyboy might just complicated things at that time. He decided to call Jill and see what she was up to for the rest of the weekend.

JILL COMES AROUND

Aaron called Jill when he got home and she was thrilled that he called. They went out on Sunday to a place that had dancing as well as dinner. They enjoyed a wonderful meal and then danced late into the evening. As they were dancing Jill warmed up to Aaron and he was excited as he had never been able to get Jill in bed yet. Jill cuddled as close as she could get. Aaron began to kiss her neck and nuzzle her as they danced and then at the end of each dance they kissed on the lips. It was getting late and then Jill asked Aaron if he was going to invite her back to his place. There was only one answer and they headed to Aaron's condo.

When they got inside the condo, Aaron turned Jill toward him and French kissed her plunging his tongue in her mouth. She kissed him back with enthusiasm and he steered her over toward the bedroom. Aaron lowered the top of Jill's dress to her waist and bared her nearly flat chest. Jill had tiny boobs but she had hard little nipples that stuck out about an inch. Aaron sucked on her nipples and she loved it.

Jill called out to me as I was sucking her nipples. "If you want big boobs you know that I haven't got them."

I stopped sucking her nipples long enough to reply, "Don't worry I am a leg and ass man. I am not into big boobs."

Jill was thrilled and that night she couldn't wait to get Aaron's cock in her pussy. He went back to sucking her nipples and then he finished undressing her. The dress fell around her ankles and she flopped back on the bed. Aaron eased her pantyhose off her and then her panties. Jill had a cute pussy with a little tuft of brown hair above the opening. She was dripping wet when Aaron slid his tongue across her labia and then worked it into her sweet passage. Jill stiffened and came with a mild orgasm as he slipped his tongue in and searched for her hooded clit. Jill screamed out loud when his tongue touched her clit. Then Aaron pushed her legs further apart and spread her lips open with his fingers. Her erect clit was standing straight out and he bit it lightly with his teeth. Jill jumped with pleasure and moaned loudly. Aaron continued to lick and nibble her clit until she lost it and sprayed his face with her female love juice. Jill tired to push him away but he held her hands firmly and pressed his tongue into her twat. Soon she was pleading out loud for Aaron to stop that she couldn't take it any longer.

He stood up and removed all of his clothes as Jill lay on the bed recuperating. Jill looked at his hard cock as Aaron approached her and he could see she was pleased. He moved between her legs and slid his stiff cock in her pussy. She was a little snugger than Aaron thought she might be and he was happy that she could feel his cock on her vaginal walls. Aaron started fucking her slowly but then he needed to cum and he picked up the pace. Jill fucked back at him throwing her pussy up at him as he plunged his cock deep in her hole. They were both fucking frantically now and racing toward their mutual orgasms. Aaron was out of control as his seed flew out of his cock and splashed against Jill's vaginal walls and deep into her pussy. She strained as she too had another intense orgasm and she worked to keep her clit in contact with his cock. They started to move slower as they regained their composure. They were dripping wet with perspiration.

The two of them rested in each other's arms and Aaron stroked Jill's body. He loved the touch of her skin, her shapely legs and curvy sexy bottom. Jill loved to have her pussy played with constantly then she would get aroused and either she would mount him or he would mount her and then they would fuck again until she orgasmed. Jill orgasmed countless times that night and she seemed insatiable. After Aaron's third ejaculation, which was always a stretch for him, he had to resort to his fingers and tongue. They eventually fell asleep in each other's arms.

In the morning Jill was ready to go again and Aaron was thankful for his early morning piss hard-on. He could always last a long time before he took his first piss in the morning so he was able to fuck Jill through multiple orgasms satisfying her needs. Aaron got up and left her lying on the bed drained from the intensity of her climax and he went to the bathroom to relieve himself. When Aaron returned to the bedroom Jill was playing with her pussy again and he was ready to get off. He crawled between her legs and slipped his cock back in to her wet pussy and they fucked until they both came again. Aaron shot wads of cum into her that morning and he was surprised with the volume and force of his ejaculation. They then showered, dressed, ate a light breakfast and then departed the condo. Jill went directly to work and Aaron headed off to his office.

EDNA'S NEWS AND JILL'S ACCEPTANCE

That Monday morning Aaron arrived at work and he was greeted by a bubbly and excited Edna. Edna had been hired to work as a female impersonator at a San Francisco club. Aaron was pleased for Edna but now he would need a new assistant. To celebrate Aaron fucked Edna in the ass and then they discussed the time frame of Edna's departure. The club wanted Edna to start as soon as possible and Edna was anxious to begin the new career. Aaron said that Edna could leave immediately and then they fucked once more as a farewell.

Aaron knew he would have to move quickly and then he remembered that Jill said that she did not like her job. Aaron asked Jill if she would be interested in working for him and she couldn't say yes fast enough. She was ecstatic and told him that she could start in two weeks. Aaron said that he would begin Jill's training in the evening at his office.

That week Jill would arrive at Aaron's office and go through about three hours of training. Then they had sex together before Jill returned to her own apartment. The following two weekends they didn't leave Aaron's condo. They had continuous sex and stayed naked for the majority of the time. Jill loved being naked and displaying her lithe body. Even when they watched television or a movie she wanted her pussy played with constantly. It was that weekend that Aaron also started playing with her ass.

Jill liked her ass fondled and the anal intrusion of Aaron's finger. He always greased her asshole with lube and then fingered her ass as he played with her pussy. Aaron fingered her asshole every time that he ate her pussy. He also fingered her bum when he fucked her doggy style. One time when they showered together, Aaron washed Jill's ass thoroughly pushing his soapy fingers deep into her rectum. After their shower he had Jill get on the bed on all fours and he licked her pussy from behind. Then he moved his tongue up to her nether hole and teased her with the tip. Aaron continued to lick and probe both her pussy and asshole with his tongue and Jill went absolutely wild. She had one of the most intense orgasms Aaron ever saw her have just from the cunninglus and anal stimulation.

I told Jill about his first assistant Cathy and how that was his first time rimming anyone. Jill was intrigued with Cathy's passion for anal sex and she admitted that she had often thought about it but had never tried it. Jill told Aaron that she trusted him and that if he wanted to try it with her that she would. Jill had a perfect bubble ass for butt fucking as it was round and smooth and perfectly contoured for her lithe body. Aaron told Jill that they would work up to it and that he would introduce her to anal toys and stimulation that would loosen her up and bring her pleasure. Aaron was really anxious to fuck her ass but he did not want to injure her or scare her away.

As Jill settled in to her new role they continued to have torrid sex and Aaron introduced her to more and more anal pleasures. He kept adding toys to their relationship and the ones she enjoyed the most were the anal beads and a vibrating dildo. The first time they used the anal beads Aaron thought she was going to pass out. He ate her pussy and he popped one bead out of her ass at a time as she orgasmed until all six beads were removed. Jill screamed out loud and her body went into convulsions with the intensity of her climax. Jill also loved the vibrating dildo in her ass as Aaron fucked her pussy doggy style. As she became accustomed to the beads they increased the size of them and they would keep increasing the size each time she became comfortable with the intrusion. They had reached the point were we felt she was ready for Aaron's cock.

JILL'S BIG STEP

One evening Aaron fucked Jill and ate her pussy until she had multiple orgasms and she was totally relaxed. He rolled her over and had her kneel on all fours on the bed. He used his fingers to lubricate her ass putting plenty of the slick substance in her asshole. Jill cooed as Aaron fingered both her asshole and her pussy simultaneously. He placed his hand in the small of her back and pushed lightly so that Jill arched her back and accentuated her curvy ass. He was so ready to fuck her ass that his cock seemed harder than ever and throbbing in anticipation of taking her anal cherry.

Jill felt the thick head of his cock between her rounded buttocks and just outside her nether hole. She knew that it was finally about to happen and she felt her stomach turn with the thought of committing such a depraved act. Aaron put an ample amount of lube on his cock and then added his saliva to it making it as slippery as possible. Once he was satisfied that his cock head was slick enough he introduced it to the tight ring of Jill's anus. Jill looked back over her shoulder at Aaron as she felt him pushing his cock against that intimate part of her body.

"Please go easy, be gentle," she reminded me.

Aaron slowly pressed against her tight opening and noticed that Jill was holding her breath. He told her to relax and breathe deeply as he continued pressing forward. Jill felt the initial thrill of her sphincter being forced open by his thick cock and her first response was to try and avoid the anal invasion. Aaron held her hips and he continued to push forward past her resisting body. Jill's mouth gaped open and she grasped the bed sheets in both hands as his cock head cleared her sphincter and lodged in her anal channel. Jill unintentionally flinched and caused more of his cock to slide inside. She cried out.

"Are you okay?" I asked.

Jill nodded and then she once again reminded Aaron to go slow. He gave her a few seconds to recover and then pressed forward again and her flower opened up for him. She just needed a few minutes to get used the unfamiliar sensation of being so filled from behind. Jill then responded unexpectedly as she accepted his cock in her ass. She pushed her butt back toward him and then moved forward. She did this for awhile and it seemed as if she were accepting and rejecting his cock at the same time. Finally Aaron's cock was buried to the hilt in her ass and they began moving together. He felt his balls slap against her pussy each time he thrust into her hot ass.

"Oh, this is so sexy. It feels so good but I feel dirty at the same time. If my parents could only see their precious daughter now," Jill murmured.

Jill had been raised by very strict parents and she had always been taught that pre-marital sex was taboo and dirty. Aaron also wondered what her parents would say if they could see their daughter with a 7+ inch cock in her ass. Jill's lust took over and she rolled her ass in tiny circles as she was consumed with her first anal fuck. Aaron looked down at her firm buttocks and he marveled at the way his thick shaft stretched her nether hole. He tried to imagine Jill's parents, whom he had never met, standing on either side of her watching as her asshole opened and contracted around his cock.

Jill reached between her legs and into her puffy cunt. Her juice was oozing from it and she rubbed her stiff and aroused clit. Aaron picked up the pace and began to fuck Jill's ass with steady full thrusts. She gasped at the new almost unbearable sensation surging through her rectum. There was no pain now but just a glorious feeling of being stuffed with cock. She felt full and a little bloated but the pain had disappeared quickly and the bloated feeling was gone also. Jill loved the taboo feeling of being filled with cock in her ass. The thought of this forbidden act along with her clitoral stimulation pushed Jill closer to yet another climax.

Aaron was trying to hold off his threatening ejaculation as Jill's movements intensified with her pending orgasm. They were both perspiring and Aaron held to Jill's shapely buttocks as he slowed his pace slightly in an effort to slow his eruption. Jill groaned loudly as her head dipped down to look between her legs and she pushed back in an effort to get more of his cock in her.

"Oh Aaron, fuck me. Fuck me in my ass, it's so good so wicked, I love it," Jill cried out.

Jill was going wild with his cock in her ass and he had never seen anyone take to anal intercourse with such abandon for their first time. Jill balanced herself on both hands as she thrust backward impaling her ass on his thick cock. Aaron knew that he could not hold out much longer. He reached around with one hand and found Jill's pussy and engorged clit. With the other hand he pinched the rock hard nipples sticking out from her flat chest. Her clit throbbed as it clamored for attention and her pussy clenched his fingers as it released her warm love juice. The points of her nipples were excited beyond desire and his cock was clamped in her well stuffed bottom.

Jill was out of control as all she knew at this point was that she was being fucked up the ass with a very thick cock and it felt fantastic. She was on the verge of her most intense orgasm ever and she struggled frantically seeking her climax. A few more seconds of rubbing her stiff clit sent Jill into a mind blowing orgasm. Her body stiffened and then spasmed out of control as she moaned loudly and struggled to breathe. The intensity of her climax was too much for Aaron and he grunted as he shot his spunk into her forbidden tunnel. Jill's eyes flew open in surprise as she felt his hot thick semen rush into her rectum and splash off her bowels. Her face was pure ecstasy as she turned to look at Aaron as his cock continued to spurt its sticky fluid up into her.

"Give it to me, cum in my ass, oh I can feel it. it's so good so nasty," Jill cooed as she was overcome with passion

Jill fell forward on the bed as Aaron continued to marvel at the beautiful ass that he had just deflowered. As she lay before him she clenched and unclenched her ass muscles causing cum to ooze out of her asshole. It looked like a small spring as the semen intermittently bubbled up and trickled out of her ass between her ass cheeks and over her puffy pussy lips. Aaron stayed hard and stroked his cock as the last tiny drops landed on her ass. He then realized that he was going to stay hard and he decided to try and fuck her ass again.

Aaron told Jill that he wanted to fuck her ass again and in an almost business like fashion she pushed her self back up on her knees. She turned her head to the side and smiled at him waiting for the second penetration. He pushed his still erect slippery cock into Jill's now gooey asshole. Jill felt her sphincter being stretched again but this time she welcomed the sensation of her ass being filled with his thick cock. As he pushed inside her his spunk from the previous ejaculation was squelched almost obscenely with his cock. His previous deposit squeezed out around his shaft and oozed from Jill's asshole running down between her buttocks and plopping on the bed sheets.

Jill was an extremely hot woman and her fucking technique was incredible. Aaron stayed crouched behind her and placed his hands back on her hips as he fed his long thick cock deep into Jill's accommodating back passage for a second time. Jill pushed her hips back at him and her bodies slapped loudly together.

"Yes, yes, oh I love it. Fuck my ass with your hot cock," Jill yelled to him and then she cried out, "Make me cum again fuck my ass with that big cock."

As before Jill lowered her head to the bed and turned it to the side as she grasped the bed sheets. But this time she grabbed the sheet in the thrones of passion and not because of apprehension. Aaron could feel her taut muscles massaging his shaft in her ass as he held on to her slim waist and he caressed her curvy firm ass cheeks. Her sphincter grabbed the base of his cock as she worked her lithe athletic body. Jill was an incredible sex partner who had just turned into a fantastic ass fuck. Aaron knew that he was getting close to losing it again as Jill manipulated his pecker with her undulations and sphincter muscle and that he would soon be adding more semen to join his previous load in her ass.

Jill had her hand back on her clit and rubbed herself frantically as she had another violent orgasm thrashing and panting wildly. He felt his seed travel along his scrotum and then spurt into the recesses of her ass. Jill felt the second ejaculation shoot into her bottom and she wallowed in the feeling of the warm liquid once again soothing her ravaged ass. Jill squeezed her sphincter muscle extracting every drop of cum from his cock until he went soft and slipped from her hot gooey ass with an audible pop. Jill collapsed face down on the bed and savored the moment. She knew now that she was hooked on anal sex and that she could expect to be ass fucked regularly from now on. Aaron flopped next to her and held her to him as they kissed and rested.

"I never thought that I could get so turned on from anal sex. It was incredible I felt like I would never stop cumming. The feeling of your hot semen shooting into my ass was unbelievable. I never expected it to feel so good just from being so full," Jill murmured as they lay together.

"I am so glad that you liked it as you know I loved fucking your ass," Aaron replied.

Jill then cuddled back up to him and they dozed in each other's arms. Later they had vaginal sex as Jill rode his cock until she came and collapsed on him as he shot another wad in her pussy this time. For the next two years Jill and Aaron would have a very steamy relationship.

JILL ENJOYS SEX IN THE OFFICE

Jill loved having sex in the office. She would lock the office suite door and then come into Aaron's office. Jill would then pretend to show him something important and she would come around to his side of the desk and lean slightly forward. Jill always wore mini skirts that showed off her shapely legs and blouses or sweaters that ended at her narrow waist. Aaron slid his hand up her leg and he felt her tremble slightly as we had played this game before and she knew where it was going. He let his hand ride up and down her stocking covered leg for a few minutes. Then he let his hand wander above her knee and past the top of her elastic top hose. Jill shivered as his hand touched the bare skin of her thigh. Aaron caressed both of her thighs and he could tell that she was getting hot. The back of his hand brushed against her panty covered pussy and he could feel that the panties were soaked with her excitement. Jill moved her legs wider apart causing the skirt to tighten around her shapely ass. Aaron rubbed her inner thighs between her legs and flicked his fingers over the material covering her vulva. Jill jumped involuntarily when she felt his hand on her pussy.