Jimmy

When my husband brought up the idea, I was aghast. Here I was, six months pregnant, it was summertime in upstate New York (think heat and humidity), and our home on the edge of the woods had small rooms. Maybe the fact that we have two bedrooms (and no kids at the moment) gave him the liberty of coming up with his proposal.

No, I’m not working, unless you consider keeping house, cooking, shopping and veggie gardening, etc., etc., legitimate work.

The scenario: One evening at dinner, when the temperatures had gone down to a reasonable level (we don’t have AC), and we were enjoying my nice casserole, hubby Angelo starts talking about his old college buddy, Jimmy. They worked together at the same company for a while. My hubby was COO (chief operating officer) and Jimmy was CFO (chief financial officer). Jimmy was, basically, the company bookkeeper. I’d heard that setup talked about many times before (and I had never met the man). But what I hadn’t heard was that Jimmy had fallen on hard times.

When his mother died, part of Jimmy had evidently died too, because he quit the CFO job, sold his company shares, and more or less disappeared. My husband had heard a few tales about him -- that he’d turned up in Chicago, and that he’d hit rock bottom.

Recently, Jimmy returned to New York and got together with Angelo. He wanted to borrow some money. But his appearance had changed. He now had tattoos, had lost weight, and certainly wasn’t as smooth as before. My husband Angelo is the kindest-hearted guy you’d ever meet, and one thing led to another -- Angelo told Jimmy he could stay with us for a couple months while Angelo looked around for a job for him -- with one condition: that I agree to the stay.

“Absolutely not!” I said. “Are you freakin’ kidding?”

Angelo nodded with resignation, then offered, “Let’s at least have him over for dinner so you can judge him better.”

When Jimmy showed up, he was completely unlike what I imagined. He actually looked rather preppy and good-looking, though the tattoos turned me off. Tall, with a thin beard, polite, on the gentle side (seemingly), he was intelligent. His clothes, though, looked like they were from a thrift store.

I finally gave in; stupid me, I suppose. If Angelo trusted him, I could too, right? Jimmy wouldn’t spend much time at our place, but instead would circulate, looking for that elusive, good-paying job. Spend nights and some meals with us. We’d let him use our old mini SUV to get around, since I didn’t need it much in my condition.

So Jimmy moved in -- but not with much. I began to relax with him, and him with me. He began to spend only half his time job-hunting, and the remainder around the house, or doing a few chores to help me out. It came time eventually for him to tell me about his time in Chicago. He was maybe too honest, because what I learned didn’t enhance my confidence in him.

He said he’d been staying in a fleabag old-folks hotel, and his stock-sale money had dwindled to nothing. I was incredulous as he told how he figured out how to get money through identity theft, by looking through discarded mail in apartment buildings. He almost seemed proud of his abilities. According to him, after a while it was relatively easy to buy things on others’ accounts, or raid checking accounts -- but, he explained, he was always careful to raid well-off people’s accounts. He claimed he was never close to being caught because he was so extremely careful. Once in a while, he’d “borrow” money from someone, and return the money later when he struck gold on someone else’s account. Honor among thieves or some such thing.

I knew if Angelo learned about this, Jimmy would be out the door, so I didn’t say anything. I was just intrigued by meeting, well, a crook.

“So, you’re an intelligent bottom feeder,” I offered.

Jimmy smiled, and then offered up the other half of his sojourn.

“I got involved with meth.”

“Jesus Christ.”

“It made me feel good. It became the pick-me-up after Mom died.”

“Are you still using?”

“That’s why I returned back here. I’ve pretty much weaned myself off it. But not entirely. I still need a little hit once in a while. Not enough to damage my health.”

“Look, Jimmy, if you’re going to stay here, with me pregnant, I want you off it entirely. No games, no excuses, no hiding drugs here or there. That’s it. Can you do that?”

“Yeah, you’re giving me a good reason to.”

“OK.”

But one other unexpected Jimmy trait that he didn’t mention cropped up after a couple weeks. When at home and with Angelo gone to work, he’d drop wearing a typical male uniform of tan trousers or levis and T-shirts around the house.

Instead, he took to wearing very loose, flowing, multi-colored shirts (a blouse if worn by a woman!), earrings, and what I suppose were man skirts. Open-toe sandals.

“Hey Jimmy, what’s with the new look? Trying to tell me something?”

“Feel more comfortable this way.”

“So, did you dress this way in Chicago? What brought this on?”

“OK, so when I left New York, I was shedding old skins, you know, like snakes do. Dropping the need to look and act like everyone else. In Chicago, I floated through the underworld, visiting all sorts of scenes, like swinger scenes, lesbian and gay bars, crossdressers and transsexuals -- then of course, the drug scenes. But I was very, very careful to avoid any possibility of getting AIDS or any of the STDs. What I found was that I was bisexual, and that I sometimes enjoyed wearing items of women’s clothing. Maybe it has something to do with my attachment to my dear departed mother, I don’t know.”

“OK, so did you ever dress fully as a woman; try to pass ... and then maybe have sex with a guy that way?”

“Oh, no, trying that would’ve been too scary. I just enjoy wearing hints of my feminine side.”

When I was left to ponder these new revelations, I came to realize that I had unconsciously felt some of Jimmy’s feminine side; that it contributed in some way to his attractiveness. When he kidded around, or whistled as he worked, or moved to music -- it was there.

I was so curious as to whether he wore panties or not. When I did laundry one day, I did find one fancy pair, but that was all.

I wondered if Angelo was concerned about Jimmy was spending half days with me. I also wondered if Angelo would get impatient in Jimmy not finding a job after three weeks, but he didn’t say a word, at least not when I was around.

One day in August, I had finished all my little chores and was laying in the sun in the back yard, wearing a skimpy sun dress over my big belly and breasts. Jimmy came over to talk.

“How are you and the baby?”

“Fine. It’s kicking sometimes. It’s making its presence known.”

“It should be such a fine-looking baby, considering your and Angelo’s good looks.”

“Why, thank you.”

He abruptly changed the subject. “Do you know that I’ve had training as a masseuse?”

“No, when was this?”

“Something I did in Chicago for a while; got my license.”

“A place for happy endings, or on the up and up?”

“Generally reputable, although a couple times, gay guys did get me to give them that special massage. Which I ended up doing when I was sure they weren’t cops.”

I laughed. “Such a life you’ve led! Is there anything at all you haven’t done?”

Jimmy laughed.

At that instant, he spontaneously began to massage my bare feet and ankles. It was so natural and ... welcome. I began to relax like I hadn’t relaxed in a long time. They say the nerves on the bottom of one’s feet connect to everywhere in the body, and that must’ve been true, because I felt a warm, subtle energy floating through me.

His strong hands communicated confidence, and his smile seemed to radiate like the sun. Somehow I felt safe with him, knowing that he was comfortable with his male and female sides.

When he finished, going no further up my legs, I profusely thanked him. “I really needed this, Jimmy. I am so relaxed, I feel like I could go to sleep .... “

“If you’d like, I’ll get some massage oil and give you a full-body massage sometime, if you don’t think Angelo would mind.”

“OK, I’d like that. But let’s just keep this between ourselves. I do like this so much, but it might bother Angelo, right? So go out and get some oil, but it shouldn’t be fragrant.”

I never asked Jimmy for another session, but all I had to do was lay out in the sun again as an OK for him to proceed. He never failed to respond.

The next time he did my legs up to mid-thigh and then my arms, neck, face and scalp. I was in heaven. I told him I’d love it if he dressed even more femininely, so he donned a loose dress along with his earrings. I kept looking to see if he was getting an erection, but didn’t notice one. I began to wonder what his dick looked like.

Oh God, Angelo, forgive your pregnant wife!

And I never put the brakes on his deft explorations of my body. The very next time, a week later, his hands also massaged and kneaded up around my derriere and cunt, but he was delightfully careful not to invade them, although I confess I wanted him to. He also began to massage my sensitive breasts and back -- and he even lightly caressed my big belly.

So, again, another week went by, and he was happily working his way up my thighs again (did he find me attractive or pregnantly repulsive, I wondered?). His hands briefly worked their way between the cheeks of my buns (slightly touching my sensitive little asshole), when he began circling my cunt’s lips. He then crisscrossed both hands over the lips several times, with the warm massage oil slightly penetrating to hidden parts within.

I was moving beyond relaxation into serious horniness. I could’ve asked him to delve down in, but there was something about wanting to be completely passive, and letting him travel my landscape. He moved up to my breasts, and there he eventually did give my nipples some oily twists and turns. And then it was up to my face and scalp.

When he wrapped up, I still couldn’t see an erection and Jimmy truly looked beautiful -- like he had enjoyed the experience as much as I had. I thanked him and said something about my having the most content baby in the world.

Then I went inside into my bedroom and played with myself to orgasm. A terrific orgasm.

Angelo commented about my seeming less ornery and happier. If he suspected anything about Jimmy and me, he didn’t say anything. Angelo and I were still enjoying sex, although it wasn’t quit as raucous as before pregnancy.

Jimmy continued to look for work, and had several job interviews. One seemed promising. He went for a second, then a third interview, and it looked like he might get the job. A gold-plated reference from Angelo didn’t hurt. I actually didn’t want him to get the job, because it might mean an end to our little touch-a-thons.

He got the job. Now he was searching for an apartment of his own. I figured there was one last chance to hit a home run, and one morning, there I was, lying in the sun again, this time with my dress hiked up suggestively. And there was Jimmy once more, responding, with a new dress on, new hoop earrings, and a sexy bottle of oil. I was turned on by the slick sound of him rubbing the oil into his hands.

“Last time, sweet,” he said. “Remember me by this. You should find a professional masseuse, because I know you enjoy this so much.”

“I doubt if I would find a better one than you.”

The tantalizing, slow, movement of his strong hands up my legs began. Slippery, sliding, warm hands helped me feel every muscle. But this time, Jimmy skipped circling my cunt and went to my arms, neck, face and scalp. My sexual parts were begging for attention. Next came my breasts, enlarging to get ready for childbirth. Jimmy ever so wonderfully took each in turn and, well, caressed them, ending with delightful nipple squeezing and running them between his fingers. I began to twist and turn a little with pleasure.

Finally, in answer to my unspoken needs, he drew his hands down alongside my belly and circled them around my cunt, my little mound. Again, he criss-crossed his hands over my cleft, putting a little pressure on my clit inside. He then rested one hand over my mound and left it there, and my screaming clit involuntarily raised my butt upwards to put pressure against his hand. Without even thinking, I started humping against it.

My cunt, I knew, was getting wetter by the second.

Soon, he pushed his hand down so that I ended my thrusts (what if this caused my baby to come early!). Then, with my eyes closed, I felt him open my vaginal lips and somehow both penetrate me with several fingers and touch my clit at the same time. I just loved to lay there and squirm a little. Then he ever so slowly began to slide those fingers around, inside and out, and I began to moan. In a matter of seconds, I exploded. Apologies to Angelo, but I had the best orgasm of my life to date. I felt like a sweaty mess.

I woke up after I don’t know how many minutes and Jimmy had left. I felt abandoned! He should’ve stayed with me ... why would he leave? Did he do his deed out of pleasure or just as a duty, as a thank-you for hosting him?

I got up, smoothed my dress out, tried to straighten my hair and came looking for him. I found him on his bed, perusing his cell phone for who knows what. He was still wearing his dress. He smiled.

“You were hair-trigger set to go off,” he quipped.

“Yes.”

“I’m glad we could go all the way, in a certain way of course, before I left.”

“Yes. And now, after so many fine massages, I want to return the favor a little, Jimmy. Be completely honest with me. Here is your chance. I will do anything you want me to, in the three hours before Angelo comes home. I mean it; anything goes. Your heart’s, or hard-on’s, desire. Your chance to live a fantasy or whatever.”

With that, I went over and boldly reached under his dress and (surprise!) panty, and held his half-erect cock in my hand. It was a little wet and sticky, so I realized he’d been excited too.

He knew I meant what I said. This was no idle, hit-or-miss opportunity. I was offering the whole kitty, the whole shmazoo.

I spent the first hour using makeup and lipstick to turn him into a sexy woman, wearing a wig of mine I’d used on Halloween. Then I helped him into my bra and panty hose, adding sexy heels and a necklace.

“Oh Juanita, the boys will flock to you like bears to honey,” I said, hugging him and applying a kiss.

And then he showed me how to slip in to his dildo and harness. I found some lube for it.

Yes, I fucked him -- his first fuck feeling like a woman. And my first time fucking anyone!

Doggy style. Pregnant woman doggy fucking a kind-of woman. As I began to slowly drill him, he found his prick with one hand and began stroking it. He began breathing heavily and then convulsed, and his milk-white sperm cascaded down his hand and onto the bed.

My god, he really loved it. I wondered -- if he had his druthers, would he prefer living as a woman -- to be fucked?

We barely managed to get everything cleaned up, remove his makeup, and get a meal going before Angelo came home and showered. We all sat down to beer and brats and beans and then the two of them went off to watch football on TV. They sat there like the two old friends they were, talking football and swigging more beer.

Myself, I just marveled at the way men’s needs are met, or not met. So many secrets and subterfuges. I would just hope that every man, at one time or another, could experience his exact richest fantasy as Jimmy did.

And that every pregnant woman can enjoy a massage or two.