His Female Client is Really a Man

Tim had just finished cutting the lawn and it was time to collect from Michelle Andrews. He always loved collecting from her as she always gave him the most incredible blow jobs. She didn't just suck his cock she made love to it. Sometimes she would make him last for 30 minutes before he unleashed a volcanic like ejaculation and sprayed his seed all over her lovely face. Once he came she would take his cock back in her mouth and suck him dry. Sometimes she would get him to cum two times before she was done with him.

She never asked for anything in return and he had never seen her naked. She was always tastefully dressed in a form fitting blouse and tight miniskirt which showed off her shapely legs and hugged her curvy bottom. He had offered many times to reciprocate by eating her pussy or fucking her but she always declined. She told him that she was pleased that she could bring him so much pleasure. He had no complaints as she gave him the best blow jobs ever. Even his girlfriend Cindy who was a great lay didn't suck cock like Michelle.

He was never completely naked either but nearly as he always cut the lawn wearing denim cut off shorts, work boots and socks. His 19 year old fit 6'2" body was well toned and tanned and she loved running her hands over him. He would be standing in her living room with his shorts and briefs down around his ankles with Michelle kneeling in front of him with her head bobbing up and down on his impressive cock. Her hands ran all over his abs, thighs, buttocks and chest as she took six of his seven inches in her mouth.

Sometimes he would cum in her mouth and other times on her body before she sucked him dry. It was always her call as to how she wanted it. That day she prolonged his release for so long that she knew it would be huge. One jet hit the back of her throat and then she pulled him out and stroked his shaft as semen flew all over her hair and face. When he was done shooting she took him back in her mouth and sucked him dry.

THE DISCOVERY

Tim had left the house after being paid and receiving another first class blow job. He loaded up his pickup truck and then he realized that he was missing his wallet. It must have fallen out of his shorts when he was getting his cock sucked. He went back in the house not bothering to knock as Michelle had said she was going to take a bath. Not in his wildest dreams would he ever expect to witness what he saw that afternoon.

When he entered the house Michelle was nowhere to be seen which was a not surprise to Tim. He spotted his wallet the floor and retrieved it. Then he heard voices coming from Michelle's bedroom. He knew she was alone and surmised that she was watching TV. However when he heard voices of people obviously engaged in sex he determined that she was watching porn. He was curious as to what she was watching and entered her bedroom.

The sight in front of him blew his mind. Michelle was totally naked with her blonde hair let down and her cute tits were on display. That wasn't all that was on display as she was stroking a small erect cock. Upon further inspection he saw that Michelle had a rubber dick stuck up her ass as she jerked off watching the porn video. He saw the pretty 30 year old woman naked for the first time. Except that she wasn't a woman.

"What the hell are you?" he blurted out

Surprised and shocked to see Tim standing in the bedroom Michelle cried out, "Oh Tim I'm sorry. I should have told you. I should have told you long ago and not led you on. Please sit down and I'll explain."

Tim sat down in the nearby chair. Michelle explained everything to Tim and obtained Tim's agreement to keep the secret. When Michelle finished explaining the situation Tim was more relaxed but still uncertain.

"Tim if you are still attracted to me I would love for you to fuck me just like you fuck a girl. Have you ever had anal sex?"

"Yes but I don't know if I could fuck you." Tim stared at Michelle's naked form and then asked, "What do they call you?"

Michelle smiled and replied "There are a few names for people like me. Transsexual or tranny for short, ladyboy is another and of course there are a few not as flattering. Now why don't you take your clothes off and join me in my bed."

Tim undressed ever so slowly as he started at the lovely ladyboy and by the time his underwear was peeled down his legs, Tim was rock hard. Michelle stared at the 7" cock and then lowered his mouth on the shaft and began to slowly suck the 19 year old dick. As he sucked Tim's cock, Michelle wondered how it would feel in his ass. It would be the thickest cock that he ever had in the ass and the prospect of it excited him but he was leery of it as well.

Michelle took out a tube of lubricant and applied it to Tim's cock. Tim stayed hard the entire time as Michelle stroked the impressive young shaft. "I like playing with your cock. You know that I could do this all day but I do want you to fuck me this time."

Michelle got on all fours and handed the lube to Tim. "Get my ass ready for your big cock."

Tim took the lube and squirted a gob right on Michelle's anus and then pushed it in. Tim worked first one finger and then a second In Michelle's asshole. Michelle put his head down on the bed and arched his back further emphasizing the shape of his curvy ass. Tim was still amazed how much Michelle resembled a young woman and it served to turn him on even more. Tim caressed Michelle's lovely ass as he lubricated the anus. Satisfied that Michelle's ass was ready; Tim knelt behind him and eased his cock into the lovely curvy ass.

Michelle placed his hand on Tim thigh as if to guide the penetration. "Nice and easy, let me stretch out for you slowly," Michelle gasped as his ass was spread wider than ever.

"Oh my, you really know you have someone in you when you're there," Michelle gasped.

"God you are really tight."

Tim took his time slowly feeding his cock into Michelle's ass and then withdrawing it slightly. Each time Tim would go a little deeper and then stop to allow Michelle to adjust. Michelle felt Tim's pubic hairs tickle his buttocks and he knew that he was buried to the hilt. Tim began a slow methodical fucking of the receptive ass and he relished every second he was in the beautiful derriere. Tim reached around as he leaned over and his hands brushed against Michelle's tits. He held the tits and caressed them teasing the nipples as well. At that moment Tim truly felt like he was fucking a girl in the ass. Tim that felt that familiar twinge and he pushed his cock all the way into Michelle's ass and held it there as he fired a barrage of cum into the rectum.

"Oh I feel it, I feel it!" Michelle exclaimed as round after round was released from Tim's cock.

Tim placed his hands on the smooth curvy ass cheeks and caressed them as her filled the lovely ass with his seed. He stayed hard and continued to fuck slowly until Michelle begged him to move to their sides. Keeping his cock deep in the shapely ass, Tim guided them on their sides and then he resumed fucking. He had his left arm wrapped around Michelle's waist and he was holding a tit in his left hand. Tim right hand sought out Michelle's stiff 3" cock and jerked him off as he fucked him. "Oh that's it play with my clit," Michelle moaned.

"Oh fuck!" Michelle gasped as he felt fingers wrap around his small erect cock, jerking him with sure strokes.

"Let it go," Tim whispered as he rocked his lower body, plunging into Michelle faster, deeper and harder, the thrusts growing more frantic. "Come for me," he said really getting into it.

Raw whimpers spilled from Michelle as his entire body stiffened with that moment of exquisite tautness that always came before his release. Michelle felt the warm tightening inside his chest, a feeling so overwhelmingly intense it rendered him breathless. Ropes of thick cum exploded from Michelle's cock onto his belly in long hard spurts, some going above his head to splash against the headboard and land on the pillow. His mouth opened in a silent scream as his body convulsed violently on the bed. He couldn't remember when he ever came so hard.

"Oh my God," Michelle gasped as he tried to take deep breaths. His cock was still spurting onto his stomach.

Looking down at the ladyboy lost in so much pleasure, Tim was in awe. Michelle was something to behold when he ejaculated. Tim wished he could hold off his own impending orgasm and keep his cock within the twitching tissue of the anal channel for a while longer. But he didn't stand a chance against those sweet contractions around his cock. He felt his orgasm start in his lower back, travel up and then down his spine, race into his balls, and then explode through his cock.

"Fuck." Tim roared as he gave in to his own urgent release, filling the rectum with his hot cum. When the last spasm faded, he held Michelle tightly to him.

Tim then placed both hands on Michelle's tits and held them firmly. The two of them then lay in bed perspiring and breathing hard from their sexual marathon. Checking the time and realized that they had been having sex for over an hour. Michelle suggested a shower and they showered together.

Tim could not keep his hands off of Michelle's shapely body and he loved washing the tits and ass. Tim got hard again and he had to try to fuck Michelle one more time. He slipped his soapy cock into the receptive ass again and they fucked until he felt the sensation of an orgasm but didn't really cum. Then they finished their shower and got dressed. Tim left the house but not before he and Michelle agreed to be discreet about their new found relationship.

ENCORE

Tim had a wonderful weekend with his girlfriend Cindy and they had marvelous sex together. She was not into anal but she was great in bed and gave good head. On Monday it was back to cutting lawns which he did to earn money for college. He had a number of clients but only one on Wednesday, Michelle.

The following Wednesday, Tim couldn't cut the lawn fast enough and when he finished within minutes they were naked and in bed together. Michelle sucked Tim's cock which helped cool Tim's jets when he shot his first load quickly in Michelle's mouth. Michelle was ready to fuck as Tim would be able to last longer before he shot his second load. Michelle knelt on the side of the bed and wiggled his bottom at Tim inviting him to play with his lovely ass.

Tim was rock hard and his meaty 7" dick looked obscenely big lined up with Michelle's tiny pink rosebud. Michelle had never had a cock as large as Tim's but he was confident that he could take him again. Grabbing the buttocks in his hands, he pulled the rubbery edges of the sphincter apart with his thumbs. Using the bottle of lube that Michelle had handed him, Tim made sure that the anus was well greased for action. He pushed his cockhead against the snug aperture that resisted him at first. However, he calmly persisted and nudged his thick tip against Michelle's taut pucker. He kept pressing into the backdoor until the elastic ring yielded, dilated and allowed the hardness to slip inside. They both gasped aloud as Tim slowly penetrated the tight slippery orifice, his cockhead disappeared into Michelle's butthole as if sucked in by a hungry anus.

"Oh Tim, I can feel you sliding in me! You're so big, oh my God!" Michelle panted as he felt his snug little hole stretching out around Tim's rock-hard girth.

Tim's cock suddenly felt impossibly huge as it opened up the tiniest, most delicate, most private of gateways to his body. In spite of the intense pressure in his anus, Michelle had a boner. He took it in his hand and stroked it as the thick cock moved past the sphincter. He stroked faster while he attempted to keep from cramping. It worked and his sphincter stopped clenching around Tim's embedded muscle and the discomfort of being stretched out diminished. It still felt strange, but in a good, arousing way. Tim's patience and his gentle caresses on the sensuous ass soothed Michelle. The sense of naughty pleasure radiated from his dilated anus and his pulsing cock.

"Are you okay?"

"Yeah, much better, I think you can give me more now. I'm ready for more cock, Tim, give it to me."

Grabbing the bottle and pouring more lube right over his dick and the stretched sphincter, Tim started feeding more of his meat into Michelle's tight ass. He went in as slowly as possible, pressing into his anus with shallow gentle strokes and then stopping, waiting, adding more lube and finally retreating a bit before restarting that gradual anal penetration all over again. Tim pushed himself a little bit further into Michelle's taut rectum. He basked in the unique, irreplaceable sensation of fucking a beautiful ladyboy ass. It was a glorious, indescribable feeling, one that he had experienced just a few times in his life with girls. Michelle was so tight that he seemed like an anal virgin. That made Tim delirious with desire as he sank more and more of his thick shaft inside the marvelous ass. Tim knew he'd be eternally grateful to his pretty lover for allowing him to penetrate the magnificent bottom yet again.

By the time he had managed to wedge his entire length inside Michelle's cock hugging rectum, he was on the verge of cumming. The look of the oily distended anus wrapped around the base of his dick and framed by those gorgeous splayed ass cheeks was incredibly erotic. However it was nothing compared to the feel of being buried to the hilt inside Michelle's beautiful perfectly shaped ass. Not in his wildest imagination would Tim have ever thought that fucking a gay ass would bring him so much pleasure. He had crossed the line and he loved every second of it. He knew then that he would have to have Michelle again and again. He wondered if once a week would be enough.

The virginal like tightness of Michelle's passage was exquisite. The slippery, velvety warmth of his anal walls snugly enveloped the aching boner from tip to base. As he enjoyed the clenching spasms of Michelle's anus, Tim gritted his teeth and tried his best not to cum too soon. He savored the delicious pressure of the spongy rectum holding firmly onto his dick, milking him and keeping his throbbing shaft cozily trapped in the anal depths.

"I'm all the way inside your ass! Your ass feels incredible, absolutely incredible! You were right; it is as good as any girl's ass, even better."

Michelle was speechless, overpowered by the intense sensations that radiated from his stimulated anal nerve endings and prostate. Without even noticing the transition from discomfort to delight, he had started to enjoy getting anally penetrated, actually reveling in the feel of absolute fullness that made his rectum pulse with ecstasy. For Michelle it was a revelation to have his asshole stuffed so full of cock.

"Tim, this is awesome to have so much cock in my ass. You are so deep in me, so hard and big in my ass!"

"You're fantastic, Michelle! Your ass is so hot and so fucking tight! You can't believe how good you look with my big dick in your beautiful bottom."

Just before Tim picked up the pace, Michelle instinctively wiggled his lovely bottom back against him. At first he gently moved his dick stuffed ass but soon he began rocking rhythmically back and forth, butt fucking himself while Tim held still.

"This feels so good!" Michelle moaned as he slid his stretched anus along Tim's tool in slow shallow strokes. He resumed stroking his own cock and cried out, "I love your big hard cock stretching me!"

Tim let Michelle follow his instincts and just watched as he worked his sweet round ass on the thick cock. The shapely frame shivered in delight as he sodomized himself with longer and deeper self-fucking strokes, Tim grabbed the lube and added more of the slick fluid to the portion of his boner that Michelle let glide out of his ass each time he rocked forward.

"You're truly amazing Michelle!" Tim exclaimed as he started to gently hump into the perfect bubble butt. "I mean it, you're so fucking hot!"

"Tim, fuck my ass," Michelle panted, looking back at Tim with a look of desire on his beautiful face. "Really fuck my ass now, I need it!"

Tim let out a contented sigh and started moving inside Michelle's warm oily asshole. He sodomized him slowly, gently, savoring Michelle's heavenly tightness and losing himself in the spectacle of his dilated anus. Tim withdrew and then gradually pushed himself all the way back inside the smooth welcoming sheath of Michelle's rectum. As Tim made love to the ass in a calm fluid rhythm, Michelle felt light-headed with pleasure and he could barely find the energy to moan out his cry of ecstasy.

Michelle unable to speak and groaning incoherently, managed to make his wanton desires clear by pushing his round tush back into Tim's skewering shaft. Michelle urged him to cram his dick harder and faster into his slick anal tunnel. Tim grabbed Michelle's firm round bubble butt in his hands and began driving his stiff meat into the clingy anus with gusto. Michelle and Tim butt fucked like animals, grunting and gasping together. Tim loved the rubbery grip that Michelle's snug rectum had on his shaft, and he was glad he had used so much lube and took such a long time letting him get used to his girth. Without the lube, Tim doubted he'd have managed to cram his big thick cock deep into the hot bowels; he was just so incredibly tight.

Michelle responded and Tim began ramming his pole into his gripping channel with longer and faster thrusts. He was amazed by the way Michelle kept up with his vigorous rhythm, pushing his curvy bottom back to meet every lustful plunge. Tim picked up his pace even more and started to really pound the butthole, burying himself as deep as he could inside the steamy rectum each time. Michelle just moaned louder and slammed back more frantically, making his perfectly shaped tush slap against Tim's groin. Michelle stroked his erect cock ever more desperately as Tim reamed his surrendered ass, he yelped and whimpered in unrestrained pleasure, an indication how much he loved every passionate second of the butt stretching sodomy. Tim found it immensely erotic to see how aggressively Michelle was participating in their anal coupling, his clear appreciation of their ass fuck fueled Tim's ravenous desire to mount the beautiful bottom again and again and again.

As time flew by, the two new lovers got totally consumed by their shared anal lust. Michelle suddenly started yelling out and thrashing as if he was having a fit. He rapidly stroked his cock and cried out as he spewed semen all over the bed covers. "Oh God, Tim, I'm cumming." Michelle's anal orgasm was unlike anything he had ever felt. It felt like his whole body was cumming. It was unbelievably, unbearably good.

Looking over Michelle's shoulder, Tim watched as five or six streams of semen shot out of his lover's cock. Michelle's sphincter clamped firmly around him and the taut rectum milked his cock in deep suctioning squeezes, Tim fought to ride out his monumental climax bucking his hips harder to keep driving his pole in and out of the contracting snug anus. He grabbed onto Michelle's round buttocks and jammed himself forcefully inside his ass over and over again. Tim was desperate to cum with him.

Lost in his mind blowing orgasm, Michelle was so far gone that he couldn't even hold himself up on his knees. His legs buckled as Tim pillaged his twitching asshole, butt fucking him with all he had. When Michelle fell forward, Tim went down with him. Holding onto his curvy rump, Tim plowed the enveloping anus with abandon, pressing himself onto Michelle's sweat slick back. Spreading his legs wide as he lay on his belly was all Michelle could do while Tim's huge cock glided in and out of his clenching rectum at a furious pace.

Lying on top of Michelle, pumping his raging boner wildly into the tight slippery asshole as he rushed to his climax, Tim went rigid and unleashed a savage flurry of butt drilling strokes. As his balls drew up and his cock started to flex erratically in the depths of the conquered ass, Tim rested his head in the hollow of Michelle's shoulder and nuzzled his neck. Nearing what he knew would be a massive ejaculation, Tim whispered into Michelle's ear.