Fall 2001, 21 yrs. old
Jackie rarely discussed her personal life. What we knew about her revolved around the shop. We knew she had a business partner in another city. We also knew she occasionally went out with some of her customers. She never mentioned having a lover.
Jackie is a transsexual woman of French Canadian descent, in her mid-forties. She stood about 5’-6”. She has dark hair and dark eyes. She was voluptuous, built like the actresses of the 40s and 50s. She had wide hips and a full bottom. She had full breasts with large, dark nipples. She also sported a 7-1/2” cock, almost 2” thick, which she used on her staff quite regularly.
Jackie also was a dominant top. She’d play bottom occasionally, but she preferred fucking women and other trannies. We assumed she’d fuck men, but never saw her with one socially.
One morning, not long after we opened, a tall, dark, elegant man walked into the boutique. Jackie’s mouth dropped, but quickly closed. She blushed as she walked meekly to this stranger. He kissed her hand and spoke softly, she blushed deeper and turned away shyly. Who was this man who affected Jackie so?
She introduced us to Mr. Delgado. He was her on again, off again lover! Currently, back on again, it appeared.
Mr. Delgado was a tall, slender man, about 6ft 6. He was dark complexioned with dark, piercing eyes. He was of Cuban descent. He dressed expensively. He had an aura of mystery and danger about him.
He kissed each our hands, but we were beneath notice as far as he was concerned. His eyes never left Jackie. There was no doubt she was his for the taking!
For the next couple of weeks, Jackie came to work distracted. She wasn't interested in fucking any of her staff, something she did almost daily. It was obvious she was a submissive bottom around this mysterious stranger.
Mr. Delgado sent a courier with an invitation for me, Tracy, and Michelle to come by and celebrate Jackie’s upcoming birthday. Attendance should be considered mandatory!
Mr. Delgado greeted us at the door and told us to make ourselves at home. We found Jackie in the living room, face down, hands tied to feet, legs tied to a bar holding her legs open. A restraint held her mouth open. On the floor lay a harness with a very thick 12 inch dildo.
If we thought the dildo huge, we were astonished when Mr. Delgado slipped out of his robe. His cock looked to be larger! He told us he was 17 inches long and nearly 3 inches thick!
“Miss Jackie is 45 today,” he said quietly. “All of you will give her 45 lashes with my whip.”
He pointed to the harness and spoke to Tracy and Michelle, “We will take turns fucking her ass while she blows out Miss Angie’s candle!”
He paused and said, “And I will give each of you 45 lashes! A bright red ass is a happy ass!”
We looked nervous, but Mr. Delgado had removed the deadbolt key. We weren’t leaving until he was ready!
“On you knees, ladies!” he laughed. “I warn you, I do not tire easily!’
Now, there were four raised asses for him to swat. He gave each of us a hard swat, then moved to the next ass. We all received more than the 45 lashes he mentioned. We all had tears streaming down our faces.
Mr. Delgado told me to hold Jackie’s mouth restraint and fuck her mouth until he told me to quit.
“I suspect you will be sucked completely dry long before we finish fucking Miss Jackie! He said, evilly.
Tracy was first to use the strap-on. She looked for lube but Mr. Delgado shook his head no. He grabbed Jackie’s ass cheeks and forcibly pulled them wide open. He stuck four fingers into her asshole and pulled her sphincter open. Jackie whimpered as Tracy slid the dildo all the way into her gaping asshole.
“Don’t be shy! Fuck her very hard!” He wickedly said. “She likes it rough! She wants it rough! She NEEDS it rough! Don’t you, Dear!”
Jackie tearfully and enthusiastically nodded yes.
Tracy grabbed her hips and rammed hard while I fucked her mouth. I lasted about ten minutes and came in her mouth. Mr. Delgado told me to pinch her nose and make her swallow it all. I started fucking again. I was giving her the rough treatment she usually gave me!
Tracy fucked her for about a half hour, then it was Michelle’s turn. I could see her malicious sneer as she punished Jackie’s ass with that dildo. Mr. Delgado was stroking his monster cock and had Tracy licking his balls. I came again, and nearing the end of Michelle’s ride, I came a third time.
After about another half hour, it was Mr. Delgado’s turn. He had me push my cock all the way into her mouth to muffle her scream as he slowly slid into her well abused ass. He worked it slowly in until he was balls deep in her now stretched wide ass. He had all 17 inches in her! I didn’t think it was possible.
“Are you ready, my Dear?” he asked her. I’m going to fuck you a long, long time!”
He pulled almost all the way out then slid it all the way in. He laughed evilly as he thrust harder and faster into her! I forgot about fucking her mouth, entranced by the sight of that monster tearing her apart.
“Did you miss this?” He laughed. “I miss your deep ass!”
Mr. Delgado looked at us and offered, "If any of you ladies like, I can train you to accept all my cock in your lovely asses!"
Michelle and I smiled and replied, "No, thank you", but Tracy looked thoughtful. She really loves having her ass whipped and will come occasionally. She brightly smiled and said, " Hell, yes"!
"After I finish here", he replied.
Mr. Delgado continued with his long deep strokes and told ustales of fucking Jackie in exotic locations. It seems he had her so well trained she'd drop to get knees with a glance from him. It would have been difficult to believe but for seeing her beautiful round tranny ass swallowing his monstrous cock!
I was still fucking her mouth. Tracy got underneath her and took her cock into her mouth. Michelle fondled and twisted Jackie's nipples. Mr. Delgado held Jackie's waist and steadily pounded her well-fucked ass.
Jackie started coming........and coming.......and coming. Tracy couldn't swallow all of it and let it spray her face. Jackie's face was as flushed as her ass had been! And still Mr. Delgado kept fucking.
Mr. Delgado fucked Jackie for over an hour before he quit. Jackie collapsed from exhaustion. She'd had two more powerful orgasms and was now spent. She'd managed to suck me off several times and I was drained.
"Your turn, young lady," he said to Tracy.
Tracy got on all fours, offering her pretty pale ass to his whip. He gave her enough to turn her bottom bright red. She was flushed, ready to fuck and ready to come!
Mr. Delgado had Michelle pull Tracy's sphincter wide open and then he lightly lubed his cock before pushing into Tracy's tight ass. Her eyes flew wide open as he slid in. She managed to take about ten inches before he hit the end of her chute. She moaned in ecstasy as he started pumping her stretched ass hole.
"My Dear, with a lot of practice, you will be able to take it all!" he looked over to Jackie and asked, " Aren't you forgetting something?"
Jackie looked over at us and said, " Thank you all for coming to my birthday party! I hope you had a good time! I certainly did!"
Jackie moved over to let Tracy suck her while Mr. Delgado fucked her very hard. Michelle and I said Goodnight and left.
Mr. Delgado called the next morning and said Jackie and Tracy would not be in for several days. He wasn't through with them yet! He said the shop would be closed the rest of the week and to cancel any appointments.
"I'd still like to train you two also, if you're interested!" he again offered. When we declined, he said, "Too bad.....you both have such nice asses. Maybe next time."
"He's bigger than anything I'm willing to try," Michelle commented. "And he can fuck even longer than Jackie!"
She invited me to her place, "Since we have time off, I have a nice seven inch strap-on you might like. I might even let you fuck me!"
We closed up shop.