Chapter 17 – Not What He Wanted

Tyler stood watching for the next twenty minutes as the kissing and fondling turned into outright groping and deep kisses. Soon Peggy had Tyrese’s thick cock in her mouth and was eagerly bobbing her head up and down, and teasingly biting the head of his dick. Rebecca and Lebron moved slower and it took awhile before Rebecca got Lebron’s pants off of him and had his erect cock in her hands.

“Tylerkins,” said Rebecca with a sly smile, “you have been a very good sissy today. Did you like cleaning the house for us?”

“Yes, Miss Rebecca,” said Tyler, his stare glued to Lebron’s cock, watching Rebecca’s hand slide up and down its length. His tongue involuntarily ran around his lips.

“I think you were a wonderful maid today and deserve a reward! Don’t you think so, Lebron?”

“I think our sissy is very frustrated, is what I think!” smirked the black man. “Tylerkins, do you want a reward for being a good sissy today?”

Tyler nodded meekly.

“And what would you like, sweet princess?” Tyler blushed as being called princess!

“M… Mister Lebron, sir. I’d… I’d like….. ”

“Yes, Tylerkins?”

“Mister Lebron, will you fuck me please, sir?” Tyler blurted this out as one fast stream of words and then hung his head in shame. He had finally said it. He had put into words the images that had been swirling around in his head for the last several hours. All the time he had been dusting and cleaning and vacuuming and serving dinner, his mind kept seeing all those cute sissy boys from the videos last night, taking thick black cocks in their boipussies, riding those thick black cocks, crying out in delight and spurting their yummy cream from their small sissy dicklettes! “I want you to put your cock in my pussy!” he repeated.

“My, my, our sissy has gotten brave!” said Lebron.

“Or just plain horny!” laughed Rebecca. “Tylerkins, sweetie, I’m not sure you have earned a fucking yet, but you may worship Lebron’s dick!”

Tyler knelt between Lebron’s spread knees and looked up into his eyes. Remembering his training, he said, “Mister Lebron, may I suck your cock?” Lebron nodded and Tyler reached out his hand and grasped the large black member.

It felt wonderful in his hand, and even better in his mouth as he eagerly wrapped his lips around the glistening knob. He was in heaven! He had a wonderful thick black cock in his mouth again and he rapturously began to suck and stroke the object of his devotion!

For the next ten minutes, Tyler did indeed worship that magnificent black dick. He ran his tongue along its full length; he took each of Lebron’s large balls into his mouth and eagerly sucked up their manly sweaty flavour; he gloried in the feeling of three then four then five inches sliding past his lips! He eagerly licked up and swallowed the precum that oozed from Lebron’s piss slit.

After awhile, he felt a tugging at his ass. He turned his pretty head to look, and saw Tyrese grasping his tail and pulling. The first couple of hard tugs dragged the butt plug partially from his ass, but each time his asshole refused to give up its captive and sucked the plug back in. On the third try, Tyrese put one hand on the sissy’s ass to steady himself and gave a much stronger pull. The plug popped out of Tyler’s ass with a loud squooching sound.

“Push, Tylerkins,” commanded Tyrese, giving his ass a playful slap! Tyler did indeed push hard, and the vibrating egg pushed out of his ass and fell to the carpet!

After being plugged and filled all day, Tyler’s pussyhole gaped wide and he felt so very empty! He needed something in there, something filling him up!

Lebron seized his head, and brought Tyler’s attention back to his cock. He placed his cock at Tyler’s painted lips and thrust his cock upward, lancing into the sweet youth’s mouth. “Suck me pretty one! Get me off!!”

Tyler returned to his sucking, but his attention was still on his ass. He smiled as he felt Tyrese’s strong fingers on his ass. The second black brother poured a copious amount of lube on his fingers, and on the sissy’s rounded ass, and using two fingers he worked the lube into Tyler’s boipussy.

Tyler raised his head and said, “Are you going to fuck me Mister Tyrese? Please put your cock in my ass pussy! I need to be fucked. I want you to be my first fuck!” He wiggled his ass, enticingly. “Please Mister Tyrese, fuck me!”

Lebron again grabbed his head, and more forcefully this time, he held Tyler’s head still as he again fucked his mouth, harder this time. “Oh, you are definitely going to be fucked, princess!”

Tyler smiled. He grinned. He wanted to laugh with pleasure as the two fingers continued to work on his ass. And then, they were withdrawn. “Are your ready to be fucked, Tylerkins?” asked Rebecca. “Are you ready to take a big black cock up your sissy pussy?” Tyler tried to answer, but Lebron would not remove his large cock from Tyler’s mouth. All he could do was try to grunt out a muffled assent, and nod his head.

And then it was time. Hands firmly grasped him by the hips, and an object rested on his ass and then trailed down to his ass. It rested for a moment at the edge of his gaping boipussy and then slid past the entrance and slowly pushed in to his ass. His ass gave no resistance. It had been opened so well that day. He knew that in future, entrance would be harder, would take more time.

But this time, his virgin fuck, the first time a black dick entered his boipussy, it slid in so very easily. He could feel it travelling along his anal chute, easily passing the depth of this butt plug, travelling deeper into him, to where the vibrating egg had rested, and then the large black dick began to meet resistance as it reached a depth where his ass had never before been penetrated!

And then the dick pulled back, almost all the way out of him, he almost cried out to tell Tyrese to leave it in him, but it again reversed direction and pushed into him again and at last, he was not just being penetrated, he was being fucked. At long last his boipussy was being fucked for the very first time.

Tyler continued to suck on Lebron’s large truncheon, but his heart was not in the suck. He was concentrating on the sensations from his ass, from his boipussy! But something was not right. He had had his plug in him most of the week. He had been fucking his own ass for several nights with his dildos. He knew how the hard plastic and rubber felt in his ass. He had expected Tyrese’s cock to feel different. He had assumed that the flesh of a hard cock would feel so very warm in his ass. But it felt just like the rubber cocks he had been plunging into his own ass!

And then…. Tyrese walked around behind the couch that his brother rested on while Tyler sucked him. “Are you enjoying your first fuck, fagboy?” asked Tyrese.

Startled, Tyler released Lebron’s dick and turned his head. Behind him, he saw Rebecca! His former girlfriend had a mean gleam in her eye as she forced the strap on dick she was wearing into his sissy ass! Rebecca was fucking him! Rebecca was his first fuck! Rebecca had taken his virginity!

Tears came to Tyler’s eyes. He had been cheated! He had wanted this moment for days now. Perhaps even since the first moment he had seen the Washington brother’s large black cocks in the shower at the beginning of the school year! But is was not either of them who were ramming a large cock in and out of his ass. It was Rebecca!

“Surprised, Tylerkins?” laughed the rich bitch! “Surely you didn’t think that after all my hard work at showing you your true inner fagboy, that I would let this opportunity pass? There was only ever going to be one person who got to fuck this ass first! And you will remember this for the rest of your life!

“Remember this, sweet Tylerkins. No one pisses off Rebecca Hunter without consequences!” With these words she thrust her hips forward and lanced her cock deeply into his quivering ass!

This was not what Tyler had wanted. He had watched the videos of sissies and their black daddies. He had seen them enjoy those thick black cocks ramming in and out of their asses, spraying their juices deep into the fagboy’s asses. But he had also seen the tenderness between the sissies and their daddies. THAT is what he wanted. He wanted to feel loved while his ass was filled with a thick cock. THIS was not what he wanted. He didn’t want to be used just as a sex toy.

Tears flooded his eyes and he began to sob.

His sobs were choked off by Lebron’s cock as he vigorously thrust his cock into the sissy’s mouth. Tyler’s mind was not on the task however, centring instead on the pounding that Rebecca was giving his ass. “Suck harder, Tylerkins! I’m gonna cum… oh shit, here it comes!” cried out Lebron, and Tyler found his mouth flooded with the black brother’s sweet and salty nectar! Tyler swallowed, but as usual, Lebron’s load was too much for him and cum oozed out of his mouth and down his chin. Lebron pulled his cock out and splashed his last jet of jism across Tyler’s face.

“I love painting your sissy face with my cum, princess!”

Tyler suddenly moaned as a streak of pleasure suddenly hit his ass! What had that been? As Rebecca had thrust her cock deep inside him, the fake dick head had hit a spot inside of him that sent delicious tingles throughout his body.

Lebron got up from the couch, and Peggy waddled, her large distended belly rigid and not swaying at all, the two black babies inside of her stretching her to simulated obscene obesity. She put a couple cushions down on the couch before taking Lebron’s place in front of Tyler. When she sat, her pussy was elevated and she grabbed Tyler’s head, pulling it down into her quim, instructing him to eat her pussy!

No longer sobbing, and in fact, beginning to take pleasure in his ass fucking, Tyler was now servicing both of his former girlfriends. Lebron lit a large joint and passed it around to his brother, Peggy and Rebecca, all taking quick tokes from the reefer! Tyler smelled the acrid smoke but was not offered a hit, as his mouth was busy licking and sucking at the blonde’s pussy!

“I think he is beginning to like this!” remarked Rebecca as she noticed Tyler’s ass pushing back to meet her thrusts. Indeed, the red headed sissy was wiggling his ass each time she jammed her strapon forward, trying to angle her cock to again find that delicious sweet spot that she had rubbed against before!

“Do you remember when I first fucked you, Peggy?” asked Rebecca.

“You mean my pussy, or my ass?” replied Peggy. “I know I was so scared of you when the boys held me down and you came at me with that monster strap-on! I’d never had sex with a girl before. The night after that school dance where Tyler and Jack dumped us just so they could play a prank on Milton… that night I was so mad and angry, and Madge and I ended up kissing and touching each other’s breasts… that was the only time I ever kissed a girl, before you came at me with that black strapon!

“Fortunately, both the boys had already been fucking me for weeks at that point and I was probably already pregnant. But I never knew you were into fucking girls, Rebecca!”

“You were my first that night Peggy! But you certainly haven’t been my last. Actually my most recent was Tyler’s mother the other day. Tylerkins, did you know that your mother is a sex hungry tramp? Oh, of course you do know. You helped Lebron fuck her didn’t you?

“You have a nice tight ass, Tylerkins. So much tighter than Mary’s pussy. Maybe next time I come visit your mother, I’ll fuck both of you!”

On her next thrust, Rebecca again hit Tyler’s sweet spot and he moaned. Rebecca drew back and thrust in, intentionally along the same route and again eliciting a delighted moan from the sissy.

“Oh yes, Miss Rebecca. Please, do that again!”

Over the next few minutes, Tyler moaned again and again as intense pleasure flooded his body. He arched his back and was kneeling upright. Rebecca grasped his nipples and toyed with them as she continued to pummel his ass. Finally, Tyler’s body quivered and shook and his erect clitty suddenly shot his small load of jism high into the air, landing across Peggy’s distended belly!

“Oh, that was sweet, Tylerkins” said Rebecca as she drew her dick back out of his ass. When it was fully withdrawn she took the tail plug which was laying on the floor at her feet and thrust it back into the sissy’s rectum! Tyler moaned again. At Rebecca’s command he licked up his own cum streaks off of Peggy’s belly.

Exhausted, Tyler sat on the couch beside Peggy who pulled his face to hers and gave him a deep kiss which he was eager to return, but for the moment he was too tired to put much effort into the pucker. From behind the couch, Tyrese stroked his head tenderly and asked, “Did you enjoy your first fucking, princess?”

Tyler still cringed at that nickname, but he knew better than to object. “Yes, Mister Tyrese. It was wonderful. I was afraid at first, but when she hit that spot in my ass, it felt so wonderful!”

Tyler was surprised when Lebron brought in warm cloths for each of them to clean up with. Evidently his maid duties were done for the day.

Rebecca fired up another joint, and the roach was passed around the friends, this time Tyler as included and he took several hits from this and the next. All of the friends sat around for the next two hours just relaxing and being mellow. Occasionally Rebecca or Peggy would tease and stroke the cock of on or the other of the brothers, and sometimes the men would tease the nipples or pussies of the girls. Tyler was not left out, several times running his hands along a thick cock or working his fingers into Peggy’s cunnie. He traded tender kisses with each of the four at one time or another, but throughout the evening, no one touched his small dicklet.

Around ten o’clock, Rebecca told Tyler that he had done well that day and perhaps they would keep him on as the maid permanently. They all had a small laugh at this which made it hard for Tyler to determine if they were serious or just having fun with him. Rebecca continued, “Tylerkins, it is getting close to your bedtime. You will be sleeping in the small room at the top of the stairs on the right. I want you to go upstairs and get ready. But instead of removing your makeup as most girls do before heading to bed, I want you to take your time and fix yourself up extra special. Then I want you to change into the clothes that are laid out for your, and then come down and say goodnight to all of us!”

Tyler headed up the staircase, remembering not to hurry, and also remembering to give his ass a bit of swish. The tail teasing his legs reminded him of the plug in his ass. Unfortunately it was too short to find that delicious spot that gave him so much pleasure!

It took him a half hour to first remove his smeared makeup and then to reapply it. He had paid attention that morning while his makeup was applied at the salon, and his efforts were now much better than just a few days ago. He then dressed in the clothing Rebecca had put out for him. Cute stockings and panties were the base, followed by a very frilly gossamer night gown. Demure two inch mules, covered in white fur fit onto his feet.

Before putting on the panties, which had the words “Virgin No More!” printed on them, he had to remove his butt plug with the tail, and insert a similar sized plug which had been left on the bed with the clothing. He washed the tail plug in warm soapy water before placing it on the dresser.

A spray of perfume added to his alluring femininity. When he looked in the full length mirror, he was pleased with what he saw, a very cute boygirl!

When he returned downstairs, it was evident that the sexual teasing amongst the brothers and the two women had risen in pitch. The boy’s cocks were slick with saliva and the girl’s pussies both glistened with their juices. But everyone took a few moments to compliment Tyler on his appearance and to give him a soft good night kiss.

Rebecca then patted him on the bum and sent him upstairs to bed, just as if he was a young child saying goodnight to his parents and heading to bed!

*****

Chapter 17 – At Last!

As Tyler lay in bed, he rubbed his legs together, sending a tingle through his body. He loved the feeling of the nylon rubbing on nylon. His dicklette was hard in his panties and his fingers toyed with the head. He thought about jerking off but he knew that Miss Rebecca would be mad at him if he made cummies without her permission. So he just teased himself as he thought back on the delicious feelings in his ass as his former girlfriend had driven that plastic cock in and out of his boipussy.

Just as he was starting to drift off to sleep, the door to his room opened. Backlit by the light from the hallway, he say Lebron enter the room. The black brother quickly took off his clothes and then slipped under the sheets beside Tyler. Tyler rolled over and embraced Lebron. His mouth eagerly sought Lebron’s and they shared a deep passionate kiss.

Tyler melted against the black man, giddy with excitement about the possibility… no, he now knew, the certainty that he was about to get his ass fucked by a real cock!

For several minutes the two lovers kissed and fondled each other, hands caressing and teasing, tongues duelling. Tyler swooned in passion as Lebron’s rigid hard cock pressed against his own small pricklet as their bodies pressed together. Soon the covers were off and Lebron was laying on top of Tyler kissing him soulfully. Tyler sighed in disappointment when Lebron moved away, but it was only momentary, as Lebron had reached for a side table drawer, from which he removed a jar of Vaseline.

Kneeling between Tyler’s legs, he pushed the redhead’s bum into the air so that his knees here beside he ears. He easily grasped the plug in Tyler’s ass and pulled it free. He then took a large glob of Vaseline and with two fingers, then three, he spread the lube around and deep inside Tyler’s rectum.

Tyler squirmed. He squirmed from anticipation. He squirmed from excitement. He squirmed from the delicious feeling of having Lebron’s fingers deep in his boipussy.

Lebron wiped his fingers on the sheets and placed Tyler’s calves on his shoulders and nudged the head of his cock at the edge of Tyler’s ass. “Are you ready for this, sweetie? Are you ready to be fucked by your first real cock?”

“Oh yes, Lebron! Fuck me! Please, fuck my boipussy!” cried the feminized sissy!

Lebron pushed forward, and his cock slowly slid into the sissy’s ass chute. Tyler’s ass had been opened by the plug and by Rebecca’s pounding, so Lebron had no trouble sinking slowly into Tyler’s hot boipussy. Tyler’s hands gripped the sheets tightly as he enjoyed the sensation of the first time a real flesh cock penetrated him. The flesh felt so much better than plastic. It was warm, alive … it was wonderful!

And though he had been fucked by Rebecca’s strapon, Lebron’s cock was thicker, and it was longer! Tyler’s ass did resist the intruder, but it failed to prevent Lebron from thrusting all the way in. Lebron bottomed out and Tyler almost blacked out from the sheer pleasure of knowing he had taken his lover’s full length into his ass! Lebron pulled back and thrust again. Then again, and again and again. Tyler thrashed his head back and forth, emitting moans of lust, and drooling. He was in absolute fucking heaven. His beautiful, wonderful lover, was finally filling his ass and pounding him with his, well, beautiful, wonderful big black cock.

All of those pictures and videos of the sweet sissies serving their powerful black lovers had led him here, to this delightful bliss.

Tyler cried out as Lebron’s next thrust struck that sweet delicious spot in his ass! “Oh god, Lebron. Right there! Fuck me hard right there! Do it. Fuck me. Fuck me!!!!!”

Lebron grinned. The sissy had truly been broken. And he loved fucking sissies, especially turning straight boys into quivering fagboys! He and Tyrese had flipped a coin downstairs to see which of the two would be the first to fuck this white boy and he had won. Of course, that meant Tyrese was having his own mini orgy with Peggy and Rebecca, but he could get his own with those white bitches any time he wanted. Well, with Peggy anyway. Rebecca set her own agenda. He smiled at that thought. The rich bitch had certainly been right about this redhead who was right now stuck on the end of his large cock!

He released Tyler’s legs and lay down across the feminized lad, his cock still buried deep. Now the two were passionately kissing as Lebron continued to pummel the sissy’s ass. Tyler squealed non stop as his sweet spot was rubbed repeatedly.

“Are you my sissy, Tylerkins?”

“Yes Lebron. Oh, keep fucking me! I’m your sissy. I’m your fagboy! I’m whatever you want me to be. Just keep pumping that cock in my pussy! Oh that is so fucking good. Oh sweet Jesus, I’m… I’m going to cum!!!” And Tyler’s dicklet spurted its cream all over his chest!

“Your ass is SO tight, fagboy. All you sissies have such tight asses, at first! But once you’ve been fucked regularly for a year or two, you will start to loosen up!”

“But right now, you have… oh god, you’ve drained me, princess! Here it comes! Get ready for your first ass dump!” And with that, Lebron thrust deep into Tyler and Tyler suddenly felt the odd sensation of copious liquid filling his ass. Lebron was cumming inside of him!. Tyler squirmed at the delightful feeling of hot cum filling up his bowels!

Lebron thrust in and out a few more times, his cock now making squelching sounds as the cum leaked out of Tyler’s ass. Finally he withdrew his cock, and flopped onto his back, panting. Tyler could feel the warm cum leaking from his ass and pooling on the sheets. Much as he wanted to cuddle, he first went to the bathroom down the hallway and grabbed warm cloths and returned to wash Lebron’s cock and to wipe up the bed. Returning to the bathroom he sat on the toilet and expelled as much of Lebron’s cum as he could, wiping his ass carefully.

Returning to bed, he had to lay on the wetspot while he rested is head on Lebron’s chest as they cuddled.

Soon the pair drifted off to sleep, a contented smile on the face of the thoroughly fucked sissy!

Chapter 18 – Encore, encore!

Lebron awoke the next morning to a delightful sensation he knew only too well. Almost every time he went to sleep cuddling a girl or a sweet sissy, when he woke in the morning it was to the delicious sensation of having his large cock sucked. This morning was no different. Tyler had woken before him and was between his spread legs, the glans of his large cock buried in his mouth, his rouged lips eagerly bobbing up and down the few inches of cock that he could manage to fit in his mouth!

When Lebron groaned and shifted position slightly, Tyler looked up, and pulled his mouth off of Lebron’s black dick. He smiled at his lover and said “Good morning, Mister Lebron, thank you for the wonderful fucking last night!” He then bit at Lebron’s cock playfully.

Lebron reached own and grasped Tyler’s arms and drew him up his body. As Tyler sat astride him, he pulled the fagboy’s face down to his and gave him a deep soulful kiss. Tyler shivered in delight! He now sat directly atop Lebron’s groin, the black cock trapped underneath him, but quiveringly hard. As they continued to kiss Lebron’s strong hands grasped Tyler’s ass cheeks and pulled them apart. He also shifted position and his cock sprung free. He moved his hips so that his cock ran up and down Tyler’s ass cleavage, toying with the boygirl!

“You have such a round girlie ass, Tylerkins! I’ve wanted to fuck that ass ever since the first time I saw you in the showers!” Tyler trembled as the big cock poked at his anal entryway!

“And you have such gorgeous eyes, princess! Even with your makeup smudged you have eyes that any man could easily fall into! I bet if you tried, you could get almost any man to kiss you!” Tyler blushed. He did not want any man to kiss him. He wanted Lebron to kiss him. Only Lebron! Well, maybe Tyrese. Yes, definitely Tyrese! Lebron’s fingers toyed with Tyler’s asshole. And his cock poked against him there to.

“Do you want me to fuck you again, Tylerkins. Do you want me to ram my cock up your delicious girlie butt again?” Tyler bit his lip and nodded vigorously. Lebron reached over to the night stand and grabbed the Vaseline. He directed Tyler to take a big scoop of the lubricant and then to reach around and grease Lebron’s cock. Meanwhile Lebron took a healthy dollop on his own fingers and pushed this inside of Tyler’s ass. Tyler shivered in anticipation!

“Push back, sweetie.” said Lebron as he used one hand to steady his dick and the other to pull one of Tyler’s plump ass cheeks aside. The sissy scooched back a bit and felt the glans of the dick make contact with his slickened pucker hole. He raised his hips slightly until he felt the head slip into his ass, and it then began to slide effortlessly up his poop chute and he sat back, putting his weight into Lebron’s lap. Tyler sighed and then squealed, his tongue rolling round his crimsoned lips as he sat, taking the full length of Lebron’s dick deep inside his ass. This was heaven he thought. This was fucking terrific!

“Oh god, this is heaven! This is fucking terrific,” he cried out! He placed his hands on Lebron’s chest to steady himself as he began to raise and lower himself on the thick cock in his ass. It felt so delicious inside of him. His own four inch dicklet was at rigid attention and quivered when Lebron teasingly flicked his finger at it!

“C’mon baby, fuck yourself on my big meat stick! You know you want to get me to shoot in that pretty ass again, don’t you!”

Tyler loved bouncing up and down on Lebron’s thick truncheon, but his leg and thigh muscles were not up to the task and he soon tired. Lebron took over, thrusting his ass upwards and spearing into Tyler’s boipussy, but this was awkward for him. He threw the sissy off of his cock and knelt on the bed, pulling a kneeling Tyler towards him. Tyler was on hands and knees, as Lebron spread his ass cheeks and thrust his full length into his anal passage. Tyler squealed at the force of the thrust. He pulled a pillow towards him and buried his head as Lebron set up a savage thrusting!

Lebron was not satisfied with his angle of penetration. He rose from his knees, momentarily pulling his cock from the fagboy’s ass. He stood over the sissy, straddling his bum, and dipped his cock easily back into the gaping asshole. He then set up furiously pounding his cock into the white sissy boi’s posterior!

“Oh yes,” cried out Tyler, as Lebron’s pumping dick thrust across his sweet spot. He was seeing stars! “Fuck my ass, Lebron! Don’t stop! Pound my boipussy!”

With one last mighty thrust, Lebron collapsed onto Tyler, flattening him on the bed. Lebron cursed and swore as his cock erupted and spewed his jism deep into Tyler’s ass. Tyler groaned at the weight pressing on him and at the delightful sensations of his ass being filled for a second time. This time when Lebron pulled out, he grabbed the butt plug which had fallen onto the floor the previous night and jammed it into Tyler’s gaping rectum.

“I want you to keep my cum in there for awhile, Tylerkins! I want you to know you are my cum dump!”

Tyler reached up and pulled Lebron’s face to his. He hungrily kissed his black lover. “I’ll be your cum dump. I’ll be your princess! Just promise me you will fuck me like that every day!” He sucked eagerly on his defiler’s tongue as he hugged him tightly.

Lebron slapped his ass playfully. “Go jump in the shower and get cleaned up. But leave the plug inside you until you absolutely have to take a dump!”

Tyler looked at himself in the mirror. His makeup was a mess again, but he thought he still looked like a pretty sexy sissy! He could compete with any of the sissies he had been watching on his videos! He smiled over his shoulder at Lebron as he swished out of the room!

He was naked as he walked down the hallway to the bathroom. He stopped at the linen cupboard to grab a large fluffy towel and a face cloth. As he passed Peggy’s room, he noticed the door was open a crack and her heard muffled moans from inside the room. Curiosity got the better of him, and he poked the door open enough to get a view of Peggy’s bed.

He expected to see Tyrese and Peggy fucking or sucking. Instead, he discovered Peggy standing but bending over the bed, her large milk laden tits swaying above her taut belly. Peggy was panting a swearing softly, as Rebecca stood behind her, wearing her large strapon, and ramming the it deep into Peggy’s ass! Rebecca was setting up a furious pace.

“Take it Peggy! Take my prick up your ass! Oh god, we should have been doing this years ago!” cried out Rebecca.

Tyler closed the door silently and continued to the bathroom where he showered and cleaned himself up. As he showered, he could feel Lebron’s cum sloshing around his bowels. When he dried himself off, Peggy was waiting outside the bathroom door for her turn in the shower. Peggy smiled at Tyler and hugged him. “Did you enjoy yourself last night, Tyler?”

“Mmmm…” said Tyler with an embarrassed smile on his face, “it was wonderful!” He giggled.

“I never figured you to be a sissy, Tyler. But now that you know your true nature, I’m glad you are able to enjoy yourself. I’m sure we are going to have so much fun together!” said the blonde as she kissed him sweetly. “The boys are sex crazy. I’m sure you will get all the fucking that you want! And you don’t have to worry about getting pregnant, like me!”

“Peggy, I don’t know what…”

“Oh don’t worry about me, Tyler. I was shocked when I found out I was pregnant. I cried a lot! But soon I realized that this was the best thing that could happen to me. I’ve always wanted to be a mother! This got me out of my mother’s clutches. You know, she actually had my life planned out for me. She wanted me to marry Jack! Yuck, could you imagine!

Tyrese has promised to marry me once he finishes university. That’s till at least four years away, but I can wait. Meanwhile I will be busy bringing up the boys!” she patted her large belly. “I suspect they are going to be quite the handful!”

When Tyler returned to his room, he sat for awhile and applied his makeup which had been laid out for him. As he was finishing, Rebecca entered to room carrying a bikini which she left for him. She also bent him over and gave him another injection in the ass, giggling as she did so and giving his ass a playful swat. As his head began to get fuzzy, she lit up a joint took a toke and then handed it to Tyler. He took a strong hit and went to hand it back to her, but she told him to finish it himself. For the next few minutes they made idle chit chat as Tyler finished the roach and then donned the bikini and the three inch clear plastic heels that Rebecca had also brought him.

Rebecca inspected his makeup and nails, complimented him on a job well done, and they proceeded downstairs. Rebecca walked behind and suggested Tyler put a bit more wiggle into his step and carry his wrists a bit more limply. Tyler complied.

Chapter 19 – Sissy bliss

Breakfast was served around the large dining room table. All five friends ate large portions and talked animatedly throughout. The food was cooked in the Hunter kitchen by Rex Hunter’s staff and Smithers was drafted to bring the food over to the gardener’s house. Tyler was a bit disappointed that the boys’ father, George, did not join them, but could not exactly say why.

As he sat down he got a delicious kiss from each of Tyrese and Lebron. He sat beside Lebron and when his hands were not busy with his food, he held Lebron’s hand briefly. As he shifted on his seat, reaching across the table to grab the plate of bacon, or to pass a plate to someone else, he could feel the hard plug in his ass, and he made small rude squelching noises as Lebron’s cum tried to leak out around the plug!

After breakfast, Rebecca gave Tyler permission to go upstairs and remove the plug and clean his ass out. As he sat on the john he could not believe how much cum slid out of his ass an into the toilet bowl! After cleaning himself up, his bikini bottoms hugged his ass much more comfortably, though he felt so empty!

Returning downstairs he found everyone out by the pool. He found an empty lounge chair. The sun was bright and it was going to be a hot day, even though it was still spring time. Being a red head, Tyler burned easily. Tyrese walked over to him and rubbed sun lotion all over his exposed body. He took particular care on the sissy’s long legs and up to his crotch. The outline of Tyler’s dicklet was easily visible inside his tight bikini bottoms. Well, it had been soft before Tyrese started greasing him up, but as soon as Tyrese touched his legs, Tyler’s boy clittie had become rigid. Tyrese managed to “accidentally” brush against it a few times as he applied the lotion, making Tyler moan each time.

The morning was spent at leisure around the pool. Coffee was flowing. A few joints were lit and shared. Occasionally one or the other of the quintet would dive into the pool to cool off. Tyler’s cockette stayed rigid most of the time – he seemed to always be excited, but did not know why! He dozed on and off, rolling over every one in awhile at the suggestion of Peggy or Rebecca.

It was a blissful morning, which stretched into the early afternoon. At one point, Smithers brought around a tray of hot dogs and hamburgers, and lemonade, though Tyler discovered this was strongly spiked with vodka. At Rebecca’s urging he drank three glasses and was feeling quite woozy.

Lebron came over and put some more lotion on his body. Tyler soon fell asleep under the hot sun. He had no idea how long he slept but he was awoken by a large splash from the pool. When he lifted his body to look at the pool, he saw that the boy’s father was swimming strokes. George Washington was a large powerful man and Tyler’s groin stirred watching him cut through the water. After ten minutes of strong strokes, George heaved himself up the ladder and out of the pool. Tyler got up and handed him a towel, somewhat disappointed to see that he was wearing baggy trunks, so that Tyler had no idea what he might be packing inside of them. Tyler, wondered why he was disappointed not to find out.

As George took the towel from Tyler, their fingers touched and Tyler felt a strong tingle through his sissy body. He looked up into George’s eyes as the black man started to dry himself. George was a very tall, very large, very powerfully built man. “Thank you for the towel Tyler! I am going to have some of that lemonade. Will you sit with me while I rest?”

Tyler could not find his tongue and just nodded. George took his hand and led him to one of the glass topped tables at pool side. The sissy’s heels clicked on the concrete as he minced along beside the tall gardener. George actually pulled Tyler’s chair out for him as he sat! There was a drinks trolley beside the table with many bottles of liquor and also a refreshed pitcher of lemonade. George asked Tyler if he would like something. Unable to find his voice, Tyler pointed one red nailed finger at the lemonade and giggled.

As they sat sipping their lemonade, George commented, “You are looking exquisitely lovely, Tyler! When I first met you just a couple weeks ago, you seemed to be a somewhat unhappy lad. Rebecca and my sons have told me a bit about you and they seemed to feel the same way about you. I am so glad that you are at last finding yourself.”

The vodka in the lemonade was very strong. Tyler wanted to tell this man that he was wrong, and that he had never wanted to be a sissy, that it had all been Rebecca’s doing. But all he could do was bow his head shyly, and giggle softly. George reached out and rested his hand on top of Tyler’s. Tyler was startled by the touch. But he did not draw his hand away.

When he looked at the older man, he saw a solidly built handsome man with graying hair and hard chiselled features. George’s chest was covered in a thick matt of curly hair which was mostly gray, but with some black throughout – what they called salt and pepper, he imagined. Tyler found himself yearning to run his fingers through that chest hair, and rest his head on that massive chest. He found himself turning his hand to actually hold George’s hand and give it a squeeze!

The two sat amiably holding hands for another fifteen minutes or so. George talked mostly about his background, and a bit about his life bringing up his sons without their mother being around and again reiterating that he was very happy not to have a woman in his life. Tyler mostly just listened, blushing Occasionally when the gardener sprinkled his conversation with compliments to Tyler on his appearance. Their hand holding had progressed into a bit of playful hand stroking and at some point Tyler realized his cockette was rigid in his bikini briefs, and that George could see his obvious excitement through the glass table top. But as hard as he looked, Tyler could not make out any sign of the older man’s own cock in his bathing trunks.

Smithers came out to the pool deck and announced that dinner would be served in the dining room of the mansion in exactly one hour. Everyone gathered up their belongings and headed inside to change for dinner. George gave his hand to Tyler to help him to his feet, then put an arm around the sissy’s waist and gave him a brief kiss on the cheek, saying that they would talk more over dinner. “Thank you for the delightful conversation, Big Daddy!” demurred Tyler as he walked away.

Rebecca directed Tyler to return to his room to take a quick shower and then to dress for dinner. She said that Peggy would help him. As everyone else trotted off to their rooms, Tyler helped Peggy with her belongings and walked with his blonde ex-girlfriend and she slowly waddled along. With her belly full of two large black baby boys, Peggy was not moving fast!

When they got to his room, Peggy told Tyler to take a quick shower as others need to jump in after him. He disrobed and wrapped a large towel around himself for his scurry to the bathroom. In the shower he scrubbed away all of the greasy sun screen. He was surprised to discover that he was deeply tanned all over his body, except for distinct tan line where his bikini top and bottoms had kept him protected from the sun!

Returning to his room, Peggy supervised as he put on his makeup, correcting and improving only a few errors that he made. “You look so sweet, Tyler! You are definitely a boy, there is no mistake about that. But you make such a pretty sissy!”

Tyler blushed at her words. He put on the bra and panties that Peggy handed to him, and then took a few minutes to get his stay up stockings on straight. “I hope Lebron thinks so!” he said dreamily.

“Don’t you be getting any ideas about Lebron, Tyler! He isn’t the type to be a one woman man – or one sissy man for that matter. That boy is never going to settle down with one girl. And if he did, it would most likely be Rebecca. That boy knows a good thing when he sees it and if he is going to settle for one woman, she will have looks AND money!

“But… but he told me he really liked me!”

“Of course he did, sweetie. And was he trying to get into your ass at the time? That boy will say anything to get a gal or sissy into bed! But then, I bet he didn’t have to try too hard, did he? You were really begging for it last night, weren’t you?” Peggy grinned, and Tyler nodded slightly.

“And don’t get any ideas about Tyrese either!” said Peggy as she helped Tyler into his clothes for the evening. Rebecca had decided that Tyler should wear a black pants suit with very feminine lines. “Tyrese is MY man. I told you we will get married when he gets out of university!

“If you want a man of your own, you are going to have to look elsewhere. But I suspect you won’t have to look very far!” Peggy removed the studs from Tyler’s ears and replaced them with some dangly earrings. She put a choker necklace around his neck and added a couple strands of pearl bracelets to his left wrist.

Peggy sprayed some perfume on Tyler and then handed him his purse. “You are ready. Now go enjoy your dinner!” She gave the sissy a loving hug.

“What about you?” asked Tyler. “You aren’t ready yet!”

“I won’t be eating with you, sweetie. Remember, I am the maid. I may not be much of a maid these days in my condition,” she grinned and shook her belly. “But I am still just the maid. Yes Rebecca and the boys are my friends, and when they eat here, I eat with them most of the time. But I never eat dinner at the big table at the mansion. If I wasn’t preggers, I would be serving the dinner.”

“But that’s not right!”

“Yes it is, Tylerkins! The Hunters were very kind to take me in and give me a job when my parents threw me out. You have to remember, this is a job for me, not just a place to live! The fringe benefits are really nice. I get fucked a LOT! I’ll be eating the same food as you, but Smithers will bring it to me over here! Now GO!”

 

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