Fall 2001, 21 yrs. Old
I’d been working at Jackie’s long enough to realize her boutique offered more than high-end clothing. She also offered quality girls for occasional outside services. We never accepted money from a customer, or “client”. Jackie paid all of us very nice salaries, more than enough to live on, and to be able to buy the nicer things. Jackie actually encouraged us to save! I had no idea, and didn’t want to know, how she was paid.
While I wasn’t exactly comfortable with how my new life was progressing, I was having the time of my life! I liked being fucked, and I was getting plenty of ass! (Or, maybe, someone was getting plenty of my ass, ha ha!) While I was transitioning from boy to woman, I was also going from slut to whore, although I didn’t see it that way at the time. (I would come to regret and hate myself for being a call girl.)
Jackie would ask the other girls to deliver purchases after hours, then give them the next day off. Jackie made a few of the deliveries, but come in the next morning ready to fuck one of us very hard. Whoever she chose would spend much of the day in her private office naked sucking her or getting fucked very hard! More often than not, I would be her plaything!
Fred would pick my up whenever we had a date, and I would change into my Hello Kitty top and very short denim cut-offs. (He bought me my first set of Hello Kitty!). I’d put my hair up in pigtails for him and we’d go to dinner, and back to my place if he had the time.
Jackie informed me a customer requested I deliver a package. He’d seen me leaving with Fred in my outfit and wanted me to wear it when I came to his place. I agreed, and changed at closing time. I was hoping for some action. I hadn’t been fucked lately and was ready.
An average looking man in his fifties greeted me at the door. His look told me my appearance pleased him. He guided me to the living room, his hand on my bottom. I was set back a little to see a very young looking brunette seated on the sofa.
“This is my wife, Dianne.” He introduced. “The package is for her.”
She watched as he slipped his hand inside my cutoffs. I was a little embarrassed for her, but she seemed uninterested in his actions. He excused himself and left the room.
“May I ask your age?” I inquired. “You seem to be sixteen!”
She laughed and replied, “I’m 19. And, yes, I’m his wife. We married when I was 17. And you?”
“As long as we look young, he won’t care!”
She led me to the bedroom and kissed me passionately.
“I think you’ll do!” she said.
Inside the box were two matching baby doll pajama sets with matching hair ribbons and teddy bears.
“Yes…..you’ll do nicely!”
She whispered as we left the room, “We’ve played this game before. Call him ‘Daddy'.”
We held hands as we returned to the living room. ‘Daddy’ was naked, sitting on the sofa and stroking his cock. We both bit a fingernail and gave him a sexy pout. (Dianne would later teach me my ‘Sex Kitten’ looks.) I could see the undisguised lust in his eyes.
He had both of us sit by him. We took turns sitting in his lap, letting him fondle our breasts and suck them through the sheer tops. He reached into our panties, fingering her pussy and stroking my small cock.
We knelt before him and took turns running our mouths along his cock and sucking him. We would kiss with his cock head just touching our lips. We alternated sucking him and licking his balls. He sat with his head resting back and stroking our hair.
Dianne was sucking when he came into her mouth. He gasped in delight when she kissed me, sharing his load with me.
‘Daddy’ watched as we kissed, fondling each other through our thing gowns. He stroked his cock as we removed our panties and moved to suck each other. I lay on my back, Dianne placing her pussy over my mouth, lowering slowly allowing me to savor her aroma. She had a slight smell of jasmine. She tasted wonderful as I licked he clit.
I ran me tongue into her now very wet pussy. While I prefer men fucking me, I do enjoy the occasional woman. Dianne could have ridden my face all night!
Dianne wasn’t neglecting me, though. She took all my cock into her warm, moist mouth. She traced patterns on my balls with her nails. The sensations were more than I could stand. I filled her mouth with my cream. She sucked harder, trying to get more.
She sat up and ground her pussy against my mouth. I lapped her juices as she rode me to a loud orgasm, screaming my name in ecstasy! She rode my tongue a few more minutes then had a second, much stronger orgasm.
We knelt in front of ‘Daddy’ as he furiously stroked his cock. He covered our faces with his load and watched with delight as Dianne and I licked his cum off our faces.
We were still kissing and fondling each other as he thanked us and went to bed.
“He may be tired, but I’m not done with you yet!” Dianne said as she led me to her room.
A couple of weeks later, Jackie handed me another box for the same address. She told me to wear my tight skirt and heels.
Dianne greeted me at the door with a deep kiss. Her husband was kneeling by the couch, a ball gag in his mouth and his hands cuffed behind him. His cock was strapped into a little cage. Dianne led me to her room, her hips swaying seductively.
Damn, I wanted that ass!
The box had matching corsets with garters and long seamed stockings. The box also had a riding crop. We helped each other dress, kissing as we went.
Her husband’s eyes were filled with lust as he saw us walk back.
“Follow my lead,” Dianne said.
Her husband, ‘the Bastard’ as we called him tonight, knelt face to the floor, ass raised. Dianne laid the crop across ass.
(Swat!) “You Bastard!” (swat!) “You though you could fool me!” (Swat!) “Didn’t think I’d find out about your secretary, did you!” (Swat!) “What’s wrong with me?” (Swat!) “Aren’t I beautiful enough?” (Swat!)”aren’t I young enough?” (SWAT!)“Isn’t my ass good enough?” (Swat!) “Don’t I get on my knees and suck you enough?” (Swat!) “Do I ever tell you no?” (Swat!)
She continued her litany, swatting his ass until It was red as a beet! Tear’s streamed down his face as she continued swatting him.
She handed the crop to me and walked around to face the Bastard. She removed the gag and inserted a restraint that kept his mouth from closing. He’d be able to suck a cock and not bite it! She cupped his chin and leaned over putting her face close to his.
“You will call us Mistress’!” (Swat!) Dianne nodded approvingly and mouthed “Harder!”
“Do you understand?” (Swat!)
He nodded and I swatted him a lot harder. He flinched and yelped. Dianne smiled, pleased with me.
“Yes, Mistress!” (Swat!)
“You will do whatever Mistress Angie and I want!” (Swat!)
She stood in front of him and commanded he lick her. He could only flick his tongue across her clit. She’d back up slightly, making him creep forward on his knees.
“You’re not licking me good enough!” (SWAT!)
I continued laying swats across the Bastard’s now very raw ass. Just sliding along a cheek made him flinch. Soon Dianne’s eyes took on a vacant look as she came. She was flushed to the top of her pointy little nipples.
She motioned me around front and bent over, grabbing her knees.
“I haven’t made him suffer enough, have I?” she winked as she asked me.
I took the hint and swatted her lovely round ass.
“Ooohhh, Yeeessss!’ she moaned (Swat!) “I’ve been a naughty girl!” (Swat!)
I must admit, I was having loads of fun!
The Bastard watched lustfully as I swatted Dianne’s beautiful ass a few more times. I pulled her close and forced my tongue into her open mouth. She cupped one of her breasts and grabbed my erect cock, stroking me. His cock strained painfully against the little cage and sweat ran down his face.
“I bet you’d like to fuck my tight little ass, wouldn’t you!” she teased. “Instead, you bent your cute secretary over your desk and fucked her, didn’t you! And you didn’t even invite ME!!! I like to have fun, too!”
She looked at me and said, “I’m going to let Mistress Angie fuck my ass! But you’re going to lick it, first and get me ready!”
Dianne told me to swat him regularly while the Bastard licked her. I swatted him for nearly twenty minutes. His ass was so red, I couldn’t see him sitting down for quite a while.
Dianne bent over and held her knees while I pushed into her. I grabbed her hips and pulled her back against me as I thrust into her ass. She was very tight and warm. Her smooth channel rubbing against my cock felt wonderful and I soon filled her with my cream.
“Don’t you wish you could taste this cream?” Dianne taunted. “I bet it’s delicious!
She bent over in front of the Bastard and let him see my cream leaking from her asshole. He wanted to lick her so bad, his face was turning red.
“Suck Mistress Angie hard, first. Maybe I’ll let you lick me clean while she fucks YOUR ass!”
I pushed my cock into his mouth and face fucked him until I was hard again. Dianne watched as I grabbed his hips and forced my way in. I didn’t use any lube. He cried out at the sudden intrusion. He was even tighter than Dianne!
She backed to his face and commanded he lick all my cream off her legs and out of her asshole. She fingered her clit and was soon moaning with delight. She came 2 or 3 times while I fucked the Bastard. He grunted each time I thrust in to him. I managed to fuck him about twenty minutes before I filled his ass.
Dianne left the room and I stuck my cock into his mouth. “Suck me clean!”
Dianne returned with a large strap-on dildo. She lubed it slightly, then rammed it into the Bastard’s ass. He cried out around my cock. I was very glad for the restraint. He was trying to grit his teeth against the pain. It took him nearly an hour to suck me clean, Dianne hammering his ass the entire time. Sweat was pouring off both of them.
We’d finished, and Dianne removed his cuffs. She commanded him to make us coffee. He knelt behind me as I sat on the bar stool, my ass hanging over the edge. He licked my ass while Dianne and I enjoyed our coffee and visited.
As I left, Dianne had removed his cock cage and was on her knees sucking him off. I suspect the rest of the night, the tables would be turned and she’d be the slave.