Stepping into It

Editor's note: this story contains scenes of incest or incest content.

*****

It has been 3 years since my Dad died and a year since my Mom found love with another man. I'm 20 now. While it may have been a traumatic experience for most people to lose their father at such a young age, for me and my Mom it actually worked out pretty well.

While I did love my father, honestly, he was a bit on the uninspiring end of the scale. He was overweight, liked to watch sports when he got home from his work at the repair shop each evening, and didn't really want to interact with me or Mom very much. He was pleasant enough and was probably pretty sweet and more active when he and my Mom met, but he checked out somewhere along the way. Thankfully his end was quick. A major heart attack and he was gone within 5 minutes or so.

As part of her grieving my Mom became one of those people who go to the gym every day for a serious work out. A pretty good way to get that out of your system as far as I could see. As a result she felt physically good most of the time and began to look really good as well. She is 5'4" tall, with long thick red hair, piercing blue eyes, soft and smooth white skin with some freckles on her hands and chest, just above her perfectly pert breasts. Her ass was now taught an exquisitely round, the shape that almost anyone would want to squeeze.

As it turned out there was a man at the gym with somewhat the same form. He was only an inch or two taller than Mom and was also a gym nut. He was in incredible shape, sporting a gorgeous 6-pack, and showing it off with short T-shirts which were his habit to wear. One could further enjoy his body because he always wore very short running shorts. The kind that almost reveal that sweet curve at the bottom of an ass, and he had a great ass. His body was always very smooth. He must have had it waxed and oiled on a regular basis. He was about as far from my Dad as a person could get. My Mom went for him completely, his name was Jared.

After dating for a while and realizing that they both loved to fuck like bunnies, inevitably, Jared moved into the house. Which was actually fine with me. He was an easy person to live with. He always helped out with all the household tasks, and he was a pretty good cook. Most of all, he seemed like a good guy. He was kind and sympathetic and seemed to treat my Mom really well, giving her the attention that she deserved. He was very tactile as well, always willing to hug and squeeze. His attention was showered on me as well, which took some getting used to, since my Dad was never like that. But I came to enjoy it as it seemed very sincere. With my Mom, that attention showed itself not only with hand holding and loving embraces, but with rambunctious sex as well.

I didn't have a girlfriend at the time (or now for that matter), so laying there in bad listening to the sounds of their hot sex became a sweet fantasy time for me. Visualizing their sweating bodies together got me hard in a flash. Soon I noticed something that seemed to come out of nowhere, I was more interested in fantasizing about his body. Thinking of his tight naked ass as he thrust into my Mom, thinking of what I thought would be his beautiful stiff pole as my Mom's lips engulfed it, thinking about his hard nipples and taught belly as my Mom rode his cock, and then thinking about how much I wanted him to do those things to me. Those thoughts excited me and scared me at the same time. Was I gay? I didn't know, but I knew I liked to think about his body. A lot!

That set me of in a new direction in terms of my porn watching. I started watching some gay porn along with my old favorites. I loved it! I loved seeing guys standing and stroking each other, guys sucking on each others hard cocks, guys sucking on each others nipples. I especially liked it when they fucked missionary style, with those strong legs straight up in the air as someones ass was filled with cum.

I am not a gym nut,as these two are, though I do have a nice body that was pretty in shape. I'm a little taller than my Mom, and more Nordic, with blond hair and blue eyes. I let my hair grow to about shoulder length. I have pale skin with not much hair on it. I don't have the 6-pack that Mom and Jared sport, but I am trim enough. My cut cock measures about 7 inches when it's hard.

Given the amount of work I had to do at the community college I attended, along with tending bar at a joint down the street, I didn't have a lot of time on my hands. So going to the gym to get fit didn't work into my schedule. Yet looking at my Mom and Jared did make me want to get fit, both to feel good and to look good. I was griping about this to the two of them when Jared volunteered to help me get a little home workout regimen going. He would coach me on some of the exercises he did, especially the ones to strengthen his core. So we made a date for the next morning in the living room. Jared was working from the office he had set up in our house, while Mom's job had people returning to her office, so she wasn't around most of the day, while he was.

When we arrived in the living room Jared checked out what I was wearing. I had put on my usual shorts and the shortest T-shirt that I had.

"Hmm...those shorts are a bit long Tyler, they'll impede your movement a bit too much." he suggested.

"Well, they're the only type I have right now, so...." I replied.

"I have an extra pair of shorts that should fit you, I'll run and get them."

So Jared returned with shorts just like the ones he was wearing, really short. They certainly wouldn't get in the way of anything, and as I took them I noticed the sleek and soft feel of them. 'These would be an upgrade', I thought. He also brought a jockstrap along with him and handed that to me.

"I also think that a jockstrap makes movement a lot easier, as well as supporting you better.....sorry, I don't mean to push these on you, let me know if I'm too much."

"Oh, no, your fine. I'm glad that you want to help, you're really very generous."

So I went into the bathroom and began to put on the jockstrap. As it turns out I had managed to avoid ever wearing one before, so I had to figure out which strap went where. And I was amazed at how little material there was, just the fabric to hold your cock and balls, the rest was all thin straps. So that when I put the shorts on, with their sleek and smooth fabric against my skin, it felt like I was wearing almost nothing at all.

Returning to the living room Jared gave me the once over. He reached inside the waistband and tugged, to see how tight the shorts were on me.

"Those should do nicely Tyler, turn around so that I can see the back." he requested.

I thought this was a bit of an unusual request but I complied, standing there as Jared checked out my ass in his shorts.

"Nice," he said.

"Umm....they fit Nicely Tyler." he quickly added.

Of course, him standing there in his shorts and cut off t-shirt, admiring my body, had my cock stiffening in his jock strap. I had no way to control the bulge that was becoming apparent, as I turned back toward him, his eyes still glued to my shorts. And as I looked down at his crotch it seemed that a bulge was appearing to tent his shorts as well.

After a moment he broke the spell, saying, "Ummmhhh...OK, Let's do some stretches to limber up beforehand Tyler. It's really important to stay loose before we do the stronger exercises."

The sexual tension in the air was so strong that it was hard to imagine staying "loose", but we went through a series of yoga-iike stretches, some cat/cow, some lunges, some triangles. He was leading me, doing the stretches along with me.

Then it came time to work on the abs. He had me lie on my back on the floor and move my legs as if I was riding a bike. My hands were cupped behind my head holding it up slightly.

"Be sure that you're tightening you abs with this one. All the way up from your pelvic floor. I'll check if you don't mind." he said.

"No I don't mind." I replied, not knowing what he meant.

Then he placed his hand on my belly just below my navel. My cock had settled down a bit during the stretching, but now it felt newly encouraged as his fingers were just inches away from my hardening shaft. He moved his hand lower, just under the band of my shorts, slowly rubbing me. His pinky was now just barely making contact with the top of the jock strap now.

"That's it Tyler, your doing a great job of keeping sti.......of keeping your abdominal muscles stiff. I can feel how they're tightening. Do you feel that Tyler, do you feel how stiff they're getting, that's what you want."

I could barely breath now, much less answer him. Yet I wanted to keep going, to keep him touching me there. To tell me again how stiff I was.

"Uhhh...Ya." was all that I could blurt out.

"Ok, now we'll try another belly exercise. Extend your legs together along the floor and lift them up together toward the ceiling. I'll stand over you and push them back toward the floor to give some resistance." he directed.

Then he stood crouching down with a foot on either side of my head. As he said, he pushed my legs down as I raised them. And from this vantage point I had a perfect view up his legs and under his shorts. He was almost squatting on my face at this point. His body was so perfectly taught and fit, so smooth, without any hair that I could see, and I could see a lot.

In fact I noticed something; while I was wearing the standard jock strap he had given me, he was wearing something else, something pink, and smooth like satin. I couldn't be sure, but I knew it wasn't a jock strap.

Did he know that I could see this? Did he want me to? The questions surged through my mind as the blood pulsed in my cock. How much I wanted to reach up and take hold of him right then and there. Given what had happened up to that point I thought that he might welcome it, but I couldn't be sure. And did I really want to have sex with my Mom's boyfriend? That couldn't end well, I thought. Though what I imagined at that moment was him lowering himself further. Lowering himself onto my face so that I could like his balls and suck on them as I pulled his panties aside. Ohh.......

"Ok, lastly, we'll do a plank." he suggested, pulling me back to earth.

I began a plank and then his hands were on me again, as he told me to keep a straight line. His hands on my abdomen and ass, assisting me in my straight line, while my cock maintained a straight line in it's strap. And was his hand making slow circles on my ass, or was I imagining that?

All too soon our session was over. I thanked him and nearly ran to the shower to relieve myself. Thinking of his taught body over me as I soaped my cock was such heaven. And were those panties he was wearing? It sent such an unexpected thrill through me, thinking that they might be. I had seen crossdressing men in some of the gay porn that I had been drawn to lately and was surprised that I didn't get turned off by it. In fact the opposite was true. So, as I stood there in the shower, my hand stroking my soaped cock, I imagined Jared's hard cock in panties, pink, frilly panties, the head of his cock protruding through the top band, waiting to be sucked. And the strongest orgasm I'd ever had up until then sprayed the tile of the shower as I nearly collapsed from the intensity of it.

It took me a while just to recover from all that was going on in my crotch and emotions, I lay there on my bed for a while trying to get a sense of what was happening to me. So many intense feelings and desires were stirring inside me. It was all a bit disorienting. Was I gay? I certainly had strong fantasies in that direction. What about being turned on by crossdressing men? Was that too weird?

I couldn't really figure it out thinking about it.

I walked down the hall to return Jared's shorts and jockstrap.

"Thanks for letting me borrow these Jared. Would you like me to put them in the wash?" I asked.

"Sure, that would be great Tyler. Would you mind putting them in the hamper down in the laundry room? In fact, if you'd also start a wash, that would be great. Then you could use them again the day after tomorrow. I'm figuring that you're up for another session, right?"

"Oh,,Ya...absolutely, I really appreciate the time and attention you're giving me with this." I replied.

I headed down to the laundry room in the basement. When I got there I noticed a pair of panties on top of the pile in the hamper. They were pink, satin, bikini panties with lace around the top edge. They must have been put there recently because they were on top of some things I had put there this morning. They had to have been put there by Jared! Did he mean for me to see them there? Did they belong to him, or to Mom?

I picked them up. They felt so good in my fingers, so soft and slippery. The next thing I did was the start of something brand new in my life. I followed the irresistible urge to take off my shorts, open the panties and step in....slowly.....savoring the feel of the panties as I drew them up my legs. What an exquisite sensation as my skin responded to the satin material. I could feel heat growing in my cock as well, so that when they were all the way up I was getting hard. They were just a little tight, but I sort of liked the way that they held my balls and squeezed my cock. Something was being unleashed in me as my cock was growing harder by the second. In fact it was pushing through the top of the panties and as I stroked it through the smooth satin, a drop of precum appeared at it's tip. I stepped into the adjoining room to look at myself in the full-length mirror there.

I loved the sight so much! I loved the look of my hard cock sticking up out of these pink panties! It was a delight beyond words and I knew I was hooked.

I knew also that I wanted more. I wanted to see more lingerie on my body. So I went back into that laundry room to investigate. In the hamper I found a pretty white bra of my Mom's. After fiddling with that and adjusting the straps I got it so that it fit pretty well. My Mom has pretty small breasts, so things weren't too far off.

Next I saw some of her black thigh high stockings with lace tops hanging up to dry.

I rolled them, as I had seen her do to put them on. My toes went in and the delicious feeling of rolling stockings up my legs was like going to heaven! The pressure of them wrapped around my legs was to die for. And when they were on and my legs rubbed together, sliding against each other, it was almost too much. Girls were so lucky to have this gift from the gods.

I sashayed back out into the other room to get a gander at the new me. God it was so hot to dress like this and my swollen cock agreed. I walked back and forth a bit and turned so that I could see at least part of my ass and did a fun spin of delight at my good fortune.

That's when I saw him. I saw him standing there in the shadows watching me. I turned to him. There was nothing I could say. Fear, shame and trepidation came upon me in a wave. I started to tremble, tears came to my eyes.

But wait, he stepped into the light and I could see that he was wearing panties. Sleek gold panties that seemed designed to hold his cock, a cock that was clearly very hard and very long. His deep brown body looked so good with those gold panties.

"Don't be worried, or ashamed Tyler. I thought that you might be inclined in this direction, so I left a little catalyst for you. Dressing in lingerie is something that I've been doing for many years.....a habit....an intense pleasure, an indulgence. So why not indulge. You only go around once."

"I..um...I..." I mumbled, unable to speak at the moment.

He gazed lovingly at me, which had the effect of slowly relaxing me.

"Don't worry, know one will know if you don't want them to, I'm good at keeping secrets. I know it must be shocking to realize that what really turns you on is a bit out of what might be called the 'mainstream'. It was for me. But now I think of it as a gift. After all, how many people allow themselves to get so turned on."

As he said this his hand began slowly stroking his cock though his panties. I began to relax more and I could feel the blood surging into my own panty clad cock. His hand now rubbing the head of his cock in those sleek golden panties had me transfixed, and I realized that I wanted my hand to touch it, to feel his hot shaft in my hand.

"You look so good Ty! Your body is so androgynous, with such a beautiful round ass." he said, interrupting my reverie.

"Do you really think so?" I responded, blushing like a schoolgirl.

"Oh yes, To be honest I've been admiring it for a while now. And don't worry I won't make you do anything that you don't want to." he said as he stepped toward me.

Rather than being frightened my body was getting hotter, my cock twitched in the panties as he approached.

"Turn toward the mirror and take a look at yourself again. Do you see how gorgeous you are in lingerie? and feel it all. Feel the taught panties barely keeping your hard cock in."

He was close behind me now, pulling the band of my panties as he spoke.

"Feel the pressure of you bra straps on your shoulders"

He moved closer and tugged the straps to accentuate the somehow delicious feeling of that pressure on my shoulders. His pantied Cock was now pressing against my ass and, almost involuntarily I pressed my ass back toward him.

He then slid the straps off my shoulders and down my arms.

"And sliding them down has it's own thrilling sensation don't you think." he whispered into my ear from behind, his hand moving around me.

And as he reached around to pinch my now exposed nipples I let out a gasp.

"Ohh....wow, I didn't realize how sensitive they are.....Ohhh that feels so good..."

With this encouragement he began to gently twist my nipples as his hot cock pressed harder against my ass and I arched my back toward him. Looking in the mirror, seeing his hands on me while I was dressed in such a sexy outfit was now incredibly stimulating. I found my self wanting him. Wanting him to do anything he wanted to me.

He turned me slowly around and drew me toward him, his arms reaching around to cup my ass, our panty covered cocks sliding against each other, my legs feeling the slide of my stockings against each other and against him. My mouth opened wide as he licked my lips and then slid his tongue deep into my wanting mouth and I began to suck it. What an incredible sensation, to have a man's tongue probing the depths of my mouth, and sucking it, so wet and warm, like nourishment.

My hands needed to feel it, I needed it so much...to feel someone else's hard cock in my hot palm! My hand slid down to touch his cock through his sleek panties. My fingers slowly moved across the smooth surface of his panties, feeling the contours of his hard heat beneath. I began caressing the head between my thumb and forefinger through the thin material. Then I pulled it out, his gorgeous long, very hard cock was now in my hand, so alive, so pulsing, so fucking hot! I started stroking it.

One of his hands released their hold on my ass and came around to the front of my pretty panties. I loved it so much that I had on such sexy panties as he reached in to grasp my hot shaft in his hand.

We stood there soaking up the moment, slowly stroking each others shafts as we kissed. Time stood still for me. I was lost in the reverie of that moment. I didn't need to be anywhere else as the ecstatic sensations engulfed me. Feeling my cock being stroked and stroking his cock at the same time was incredible. As if we had one cock, one fucking hard cock that was feeling such intense pleasure. And his tongue so deep in my mouth now as I allowed him to enter me there, wanting him deep inside, wanting to consume him.