Jimmy Makes a Special Friend

A1386G side story #1: Jimmy makes a Special Friend

It was eleven o'clock at night, and my mistress had been sitting in the dining room with her lab partner Daphne for several hours, when the subject of their conversation had turned from their homework to comparison of their individual slaves. I had been bringing them a fresh pot of coffee from the kitchen at the time.

"Constance, your boy does have a cute butt and yummy legs under that skirt," Daphne said, leering at me, "how did you do it?"

"It's quite easy actually," mistress replied, waving a pen slightly in her hand, "it's all about exercise. It's amazing what an hour on an elliptical machine three times a week can do."

I absolutely beamed at the compliments as I put the carafe down on the table. Out of the corner of my eye I noticed her look at me, and I couldn't help but see her smile from the compliment change into the one expression I feared more than anything.

"Of course," mistress continued, as she looked back at Daphne "if you wanted to do a direct comparison, you could just call your boy in here. He does have some good points as well."

"Of course." Daphne said, with that same feral look in her eyes, before calling out. "Jacob!"

I tried to back out of the room before anything could happen, only to find my way blocked by another body.

I heard a voice from behind me. "You called?"

It was definitely Jacob. There were only four people in the condo after all.

"Alright," mistress said, "both of you, step up to the end of the table, and strip down to your underwear."

Daphne nodded her consent to the order, and Jacob and I complied, even if I was beet red from a mixture of embarrassment and fear.

After removing my slippers, I first untied and removed my apron, folding it before placing it on a nearby chair, as I then did my skirt and blouse in turn. This left me only in my headpiece, stockings and a lace thong.

At the same time, I got my first look at Jacob. He was black haired and darker than I was, and a good thirty centimeters taller to boot. He had somehow concealed a well cultivated physique with ample chest hair under those ridiculous poet shirts and skinny jeans Daphne made him wear. That lucky bastard got to wear boxer-briefs though.

I noticed that mistress was licking her lips as she sized up Jacob.

Daphne had by this point gotten up and walked toward us for a closer look, and was running a finger down my chest rather seductively. I swallowed reflexively, and looked toward my mistress, who just smiled that thin, evil smile as she took it all in stride.

As Daphne hung off of me, I noticed Jacob's growing jealousy.

"You know, it's really a shame you have your boy hide such a yummy body under a maid uniform of all things." His mistress said to mine, "and it's so easy to ruffle his feathers. Do you mind if I...?"

"If you'll extend me the same courtesy." mistress interrupted.

"Jacob," Daphne said, "remove the boy's underwear, and then your own."

I really hoped this wasn't going where I think it was, but then again, mistress was the sort of person to do these things, and she got along a little too well with Daphne.

Either way, Jacob complied with the order, hesitantly lowering my thong to the floor, whence I then stepped out of it, and then moved on to stripping himself.

Daphne took the opportunity to crouch down in front of me, and begin playing around with my penis and scrotum.

Constance came over and examined Jacob, lifting up his rather large penis in a rather clinical fashion before inspecting his scrotum thoroughly, if rather dispassionately.

"Daphne," mistress said, "is your boy-toy a grower or a shower?"

"A shower," she replied, glancing over, "Sadly he's maybe at half mast right now. Constance, Jimmy has some recent scars on his scrotum, did you just get him fixed or something?"

Of course not, why would I need to be fixed? I was a good obedient boy who always used a condom, and made sure Mistress kept up to date on her shots. As a result, she had gotten me unfixed for Christmas.

"Just had it reversed actually." mistress replied, "I'm going to have him breed one of my milk-sisters for her birthday, since my parents decided to keep her instead of trading her."

I smiled. That was going to be her best birthday ever, and I was going to rock her world.

I saw mistress looking at me with the widest, narrowest smile I'd ever seen on her. I shuddered. "Daphne," mistress said, "I think Jimmy needs to be put back in his place. Do you mind if I borrow Jacob to do it, and make it a learning experience for my slave?"

"Go ahead." Daphne said as she grabbed my wrists, "Jacob's never had another boy before."

"Jimmy, I want you to suck on Jacob just like you do Mister Happy" mistress commanded, referring to her favorite strap-on.

Then both of them started chuckling, apparently proud of themselves, as Jacob seemed to get more erect, and I shuddered. Daphne then released my wrists, and I crouched down to the appropriate height.

Just as I had with my mistress' toy, I reached my hands around Jacob's back as I licked his penis from base to tip along the urethra, before plunging the whole thing into my mouth. He shuddered, and I felt him stiffen further as I bobbed my head up and down a few times to ensure proper lubrication across the whole shaft. I was going to need it, now that the damned thing was the size of a fucking knockwurst, and just as big around. Clearly, this was why Daphne was such a happy woman.

After a moment of that, Daphne spoke. "Good," she said, "now Jimmy, bend over on the table. Jacob, get behind him."

I complied, and immediately felt someone hold my butt cheeks open, before Jacob entered me quickly, and bent over on top of me, as he held my wrists flat against the table. I clenched my eyes shut and grimaced at the sudden invasion.

As he began to pull back from his first stroke, he whispered into my ear. "I'm sorry about this, I'll try and go easy on you."

I could only grunt in response as he thrust back in, and continued in his attempt to tenderly pound my ass. It was still quite painful, but this way I felt something other than him licking my ear, and the sensation that my ass was going to tear apart.

I heard mistress laugh that evil fucking laugh from her position behind us, before someone smacked Jacob on the ass, forcing him to speed up. He managed to find my prostate though, and after I writhed a bit, and moaned in fake agony, he kept hitting it to my relief.

A camera shutter sounded. He started to pant from the exertion. My erection pressed painfully against the table.

Apparently he was beginning to reach orgasm about the same time I was, since I felt him slow down and clench his prostate.

"Mistress, may I?" Jacob said in between pants.

"Ngh, Mistress please!" I said groaning.

"Please what?" Daphne replied.

"Mistress, ugh, may we please come?" I said for the both of us.

My Mistress responded. "Jacob, pull him up."

I felt him release one of my wrists, as he pulled himself up slightly, and jammed his now free arm under mine, before he forced me back into a standing position as he leaned backwards slightly.

I opened my eyes. My mistress was sitting there with a happy look on her face, as she held a mostly-empty coffee cup up to my erection.

"You may both cum" my mistress said.

Immediately after she said that, I felt Jacob release his ejaculation, which shot inside me with considerable force, and a warm feeling spread throughout my body.

As I shuddered in near-synchronicity with Jacob, I ejaculated, and my mistress caught it in her coffee cup.

Jacob then pulled out of me and stepped back as I collapsed in a heap on the floor when my legs gave out.

"Jacob, be a good boy and clean up your mess," Daphne said.

My mistress added in, "Have Jimmy help you, and then give him a taste."

"Yes mistress," Jacob said rather reluctantly.

Jacob then squatted down and spread my cheeks, before sucking what ejaculate he could out of my anus, before withdrawing his tongue.

Then while I was barely lucid, I turned myself over to complete my mistress' instructions, and cleaned off Jacob's now flaccid penis after he placed it in my waiting mouth. Once it was again wet, and I had cleaned it, Jacob withdrew his organ, only to force my lips open with his, and he drove the tainted ejaculate inside my mouth.

I gagged at the sudden intrusion, only to feel my mistress' finger rubbing my throat. I thus swallowed the vile mouthful before gasping for air.

"Now then," Mistress said, "both of you go take a shower, and take your time with it."

I struggled to my feet, and Jacob put my arm over his shoulder to steady me as we walked out of the dining room and on to the bathroom off the kitchen.

As we passed through the kitchen, I heard Daphne shout after us "And wash your mouths out!"

Then I heard the two mistresses started giggling like school girls.

Jacob then looked over at me, and I looked up at him. "Good job," he said as he ruffled my hair, "Also, let me be the first to say this you lucky transvestite bastard, but congratulations on the baby."

Even in my rattled state, I smiled irrepressibly. I was actually going to get to be a father some day.