Jimmy D

This story is set in another time. Before Covid, before Aids, before Vietnam even, though just barely. The early 1960’s were a more innocent time perhaps, but people were very cautious and tended to stay locked up in their closets.

It all started with a phone call. Half the time I just ignore the noisy contraption but this time I picked it up and guess who was on the other end: Jimmy D! He is an old childhood friend from our neighborhood at a time when there weren’t many kids there our age. We were both born between the end of the depression and the end of WW 2. So we weren’t baby boomers where there are so many little kids running around they’re tripping on each other. We did everything together. I’m amazed we never got in trouble with the law, or killed ourselves, so I guess we were just lucky. I hadn’t talked to him in five long, event filled years.

Jimmy was 6 months younger than me, and so in school he was actually one year behind me. As soon as I graduated from high school I volunteered for a short (four year) career in the Air Force and thus avoided getting caught up in the Draft. Yes, we had such an abomination in my youth. Jimmy did the same thing a year later, except he opted for the Navy. We hadn’t seen each for a long time.

Jimmy D, (DeAngelo for long), had just escaped from the Navy and had gotten my phone number from my folks. We chatted for a while and then he said he wanted to come over for a visit. As I was now a hard working, tax paying employee of a major sweat-shop in the Big City, I suggested Saturday would be a good day to do it. He agreed. Then I asked him if he still enjoyed some of the things we did to each other back in High School?

His reply: “Why do think I joined the Navy?”

“Well”, I responded, “Perhaps I can put on a horny little show for you. About noon Saturday?”

Backing up just a little, I should add that I gave Jimmy his first blowjob when I was a freshman in high school. We traded blowings off and on with an occasional ass fucking for variety till I ran off to the USAF. While we both liked girls there was something about all the rigamarole that one must go through just to touch a titty, much less doing anything truly satisfying that for two horny young boys who wanted to get past jerking off, these perverted couplings just worked out better. And quicker, I might add. I should also add that while in the Air Force I had led a rather chaste existence. Since I’d gotten out I was trying to make up for lost time. Now maybe we could resume the fun with some orgiastic episodes of things we’d learned, or maybe just heard about since, thrown in for good measure.

I had a friend I occasionally hooked up with. She was a very cute little, what we now call she-male, that went by the name of Michelle. I knew Jimmy would lustfully enjoy her company.

When I called her up she was very happy to be welcoming home a new service veteran. She also mentioned that she had been practicing a strip routine with an appropriate outfit and that now might be a good time to show off her skills to a small, but appreciative audience.

Come Saturday morning I was up early getting prepared for a full day of orgying. After breakfast, I was in my pint-sized bathroom douching out my ass before using an empty wine bottle with a smoothly tapered neck for expansion of my rectum and comfortable size cucumbers thrown in for depth training. I must admit ‘my comfortable size’ was getting bigger each time I did it. The cuke was inserted all the way in till it disappeared and then a second one pushed it in further until that one was all the way in. While I was entertaining myself thusly the phone rang and I staggered out to answer it. It was Michelle saying she was just leaving her place. I said I was indisposed at the moment, but that I would leave the front door unlocked for her. A few minutes later I was using the wine bottle, neck first, on myself, when I heard her come through the door.

“Yoohoo’, she called out.

“I’m in the bathroom”, I replied, “come on in”.

After a minute or so she stuck her head through the door, saw what I was doing, smiled and said “No wonder you’re feeling a little loose lately”.

I decided I’d had enough ass stretching for now and finished up by an actual, conventional shower, did a quick trim job on my pubic hair leaving a heart shaped rim of fur around my dick and dressed up in sweat shirt and pants. I wanted nothing to get in the way of a quick strip.

When I emerged from the bathroom I found Michelle in my bedroom with her new stripper outfit spread out on my bed.

“What do you think?” she asked as she held up a tiny G string covered in feathers and rhinestones.

“Turns me on. I gotta see you take that off.” I replied.

“Oh you will. This and everything.”

“That will give Jimmy the thrill of a lifetime, and me too. You don’t do this professionally do you?” I asked.

She gave me her ‘WTF, are you crazy look’ and started stepping out of her street clothes. This was a good show too, and I pulled my sweatpants down and started stroking my ever eager cock. When she pulled off her panties I jumped in front of her, got down on my knees and sucked her floppy cock into my mouth all the way down to the base. She gyrated her hips around to fuck my face and I felt her cock growing and stiffening while she tried to reach the back of my throat. Then about the time it was fully erect and things were just starting to get interesting , she threw a wet blanket on the proceedings by saying, “Isn’t your friend supposed to show up about now? I mean this little show is about him, isn’t it? Hmmm.”

Somewhat sheepishly I replied, “You just think he can give you a better blowjob than me.”

“Oh, you poor itty-bitty lil boy.” With this rejoinder she bent over and rubbed her boobs in my face. And, speaking of boobs. When I first met her, Michelle had boobs that could best be described as about the size and shape of fried eggs. But recently, she started using a new estrogen cream that uses an estrogen derivative that I can’t even pronounce and it works much better than her old stuff. She’s up to a ‘B’ cup now she says. I can hardly wait until tomorrow and the next day. (Here I am, an admitted Homo who loves to suck on boobs. The bigger the better. Go figure.)

At this point the rumor is that the doorbell rang and my friend Jimmy D. started pounding on the door. Not true! It was a good two minutes later that Jimmy showed up at my door and he didn’t pound on it at all. So much for rumors.

I opened the door and there he stood, Jimmy D’Angelo, a little older, more mature than I remembered, but still the same overall. He is about five foot eight, an inch shorter than me, but wider in the shoulders. That’s what lifting weights does for you. He has black curly hair, unlike mine, mouse-brown and straight. We shook hands and I invited him in. I noticed Michelle had retreated to the bedroom and was just closing the door.

After I popped him an obligatory Blue Ribbon beer we sat down in my undersized living room and started to catch up on five years of war stories. (The first liar doesn’t stand a chance, the second liar can always beat the first story.) We were falling out of our chairs laughing when I thought I heard a little squeaky sound calling out my name. Oh yeah! Michelle, I’d forgotten all about her. I retreated to my bedroom and there I found Michelle all dolled up in her stripper outfit with a slightly pissed expression on her lovely face.

“I’m sorry, I’m sorry. I almost forgot about you”, was my defense before she could lay into me.

“I’ll introduce you to Jimmy right now”. She merely handed me a 33 rpm record and told me to start it up on the phonograph. I checked the label, ‘How to Strip For Your Husband’. Mmmh, seems appropriate.

I came back out into the living room, set the record on the phono’s spindle and started my totally unrehearsed introduction.

“Ladies and Gentlemen… Well, Gentleman, Jimmy uhh, er, for this special occasion we have for your entertainment a special presentation by a very special lady who has been persuaded to show you every, and I do mean, every-thing. Let’s give a big hand for a little lady… Michelle”.

With that I set the phono needle down on the disc and the opening, rather raunchy notes filled the room, then the door to the bedroom opened and Michelle sauntered out all sparkly with a pair of feathery fans teasing the eyes. I glanced over to Jimmy and saw a rather puzzled expression on his face. I tried very hard not to laugh.

Michelle settled into her routine, taking little dance steps, twirling around on her toes, playing peek-a-boo with her fans and working up a sweat. I was working up a sweat too, I’m not sure about Jimmy.

I reached inside my sweatpants and groped my cock. After a bit more dancing Michelle slid out of her see-through skirt and tossed it aside. This mostly exposed her round little butt which she then aggressively shoved into Jimmy’s face. He took the opportunity to plant his lips on her buns and to stick his tongue under the G-string strap between her cheeks. She turned around and made a clucking sound in mock disapproval.

Next to come off was her bra leaving just her pasties on above the navel. and they came off next. Her ‘B cup’ boobs, now exposed were given a good side-to-side shaking. Her next move was to bend over in front of Jimmy and gyrate her boobs in his face with gravity helping them hang down a bit farther.

Jimmy, warming up to the show, gave each of her nipples a good sucking and settled back in his seat with a big smile. I was warming up too, as I had pulled my sweatpants down around my knees and was flopping Mr. Happyface back and forth with some enthusiasm. Jimmy noticed what I was doing and started his pants zipper on a downward path.

Michelle, for her part, undid the snap on one side of her feather and rhinestone covered ‘G string’. She then turned around, shaking her butt and unsnapped the other side. At the same time she closed her legs up and tossed the ‘G string’ over her shoulder into Jimmy’s lap. I was seated off to her side and could see what she was doing, but Jimmy’s view was just Michelle’s butt. She was pulling her cock out to full length and relieving her balls from being stuck to the insides of her legs. She then turned round facing Jimmy and started twirling her cock around like an airplane propeller. I wish I’d had a movie camera. The expression on his face was priceless. First his jaw nearly hit his chest. Then a really big smile filled his face. And last he started laughing, uproariously. I joined him as I thought this was a super show Michelle and I had pulled off. She now stepped onto the sofa straddling Jimmy’s legs and leaning forward rubbed all her private parts onto his face.

Jimmy was obviously enjoying this and had Michelle’s balls in his mouth. I saw he was pulling his cock out of his pants, made difficult by how stiff it was getting. I figured it was time to give him a little help and knee-walked over to him, grabbed his cock, slipped it into my mouth and finished the job of undoing his pants and pulling them off.

The rest is sort of blurry, but fun. I remember Michelle sat down in Jimmy’s lap sliding his cock into her sweaty and well lubed ass. For my part I stuck my head into this confusion of arms, legs and other body parts and found Michelle’s cock which I slobbered all over and tried my darnedest to swallow. I know I found bottle of hand cream, smeared a liberal amount on my middle finger and slid that up Jimmy’s ass. I knew from past experience that this brought him much pleasure. As I was sucking Michelle’s dick she sped up her rocking motion with Jimmy’s cock sliding in and out of her ass. In synchrony with this I sped up my sucking on her cock. This whole thing was working up to a climactic climax very quickly.

Jimmy got off first. He was making a lot of snorting and snuffling noises and with one final hip thrust lifted his butt, and Michelle, and my head up seemingly half-way to the ceiling. He then dropped down and made three more upward thrusts as he filled Michelle’s little ass with his sperm. Michelle followed his cue and started spurting deeply in my mouth. She had her cock crammed as far as possible into the back of my throat so that I couldn’t swallow and the next thing I knew my mouth was full of her juice. Her hands were on the back of my head pushing me down as far as she could. Since I was breathing as fast as possible through my nose a fair amount of this cum made it up into my nasal passage and sinus which caused me to gag and choke and almost vomit. Do you think Jimmy or Michelle cared about my distress? Not hardly! A mixture of cum and snot drooled out of my nose and edges of my mouth. I managed to swallow enough of Michelle’s cum to make breathing possible again. I know that by now I looked like something out of a porn-horror movie but you know, these things aren’t rehearsed, they just happen.

Jimmy looked down at me wide-eyed and started laughing. Michelle turned around caught sight of me and started making sounds of sympathy but then let out a loud howl of laughter too. I fell onto my back and grabbed a handy Kleenex or two, wiped my face and blew my nose very satisfyingly for a long time.

“That’s the second blow job I’ve given in the last minute”, I gasped