A New Day Dawning

When I heard that Jeff was going to spend the summer at home this year I was thrilled. It had been a few years since my son and I had been able to spend this much time together. He was finishing his third year of college on the west coast and we hadn’t really had the money for a lot of visits to see each other, and when we did they were brief and busy. To be able to relax with him around the house was something to cherish. He could now work from home at his summer job placement. High tech was sure helping our family life this year.

One of the reasons he was coming home was to keep me company. Laura, my wife and his Mom, was going to be staying with her ailing mother for most of the summer, unless her mom passed away before the summer’s end. She is indeed the “good daughter” and will be waiting on her mother hand and foot during this time. As unfortunate as the reason is, in some ways it is good for us to spend some time apart. We have very different styles, which became more apparent after Jeff, our only child, left for college. She tends to be on the more conservative side while I’m a bit looser and more liberal. I enjoy going out to the clubs occasionally to hear music and dance with my friends, while she would rather stay home and read, listen to a podcast, or knit while watching a movie. The music scene doesn’t start until late so I end up arriving home at 1 or 2 in the morning. She says she doesn’t mind, and I don’t mind that she doesn’t like to go out, but there seems to be a widening space between us. I’m hoping that a little time apart will help us appreciate each other more.

I had accumulated a lot of comp time at work, and along with my vacation time I could spend much of the summer focusing on Jeff.

So, I’m scheduled to pick up Jeff from the airport this evening. The airport is about an hour and a half away which should give us some time to catch up on the drive home. I’ve cleaned up his old room and even put some flowers in there to greet him upon his arrival. Just thinking of him sleeping in his old bed warms my heart, we have always been very close, he tells me pretty much everything that happens for him.

We find each other in the huge, busy airport and embrace. It feels so good to hold each other again, having always been a tactile pair. We exchange the usual chatter about the trip and the food and the weather while we make our way to the car. Once we’re on the highway we can settle in for a little while to talk.

I begin, “Jeff, I can’t tell you how much I’ve been looking forward to having you home for the summer. It’s hard to keep up with you with a few phone calls and visits. What a treat this is!”

“Thanks Dad, there’s so much that’s been going on, so fast, it will be great to slow down and enjoy a different pace, and to have you to myself is a joy for me. Umm…not to say that I don’t love Mom, you know I do…but this will be different…” he replied.

“So…yeah…tell me about what’s been going on for you, I’m all ears.”

“Well, as you may have heard in the news, or maybe in other ways, there has been a lot of talk and action around how people view themselves in terms of their gender identity and sexuality. It’s kind of like a frontier that is up for so many people on campus and other places these days. It feels like one of the ways that our culture needs to break through some old stories that are not very useful, and can be pretty damaging for us all.” Jeff began.

“Yes, it does seem to be something a lot of young people are thinking about these days. I remember speaking to you about your not needing to be a macho man and how my own not being the ‘alpha male’ had affected me through my life. Is that part of what your talking about?” I asked.

“Yes, exactly Dad. And it’s gone a lot further down that road. It’s really like an evolution of that idea, the idea that it’s OK for men to show their feminine side, that we’re not one hundred per cent male or female and it’s OK to show that in whatever way you choose to. Otherwise it gets all muddled up and can come out in weird ways, like homophobia or hating yourself for feeling the feminine inside of you, or even violence. I think we have to allow ourselves the complete freedom of expression.” Jeff continued, his voice getting more powerful as he spoke.

“Well, I can see that you’re really feeling this one strongly Jeff, that’s great. Speaking more personally, how has this affected you?” I wondered.

“Well, I hope I can speak freely about this Dad. It may get a little uncomfortable for you, though I think you’ll understand. I don’t mean to shock you.”

“Jeff, you can always tell me anything at all. Don’t worry about shocking me, I’ve got a lot of capacity. Fire away!”

“So, first I wanted to say that I don’t feel like I would want to do anything like changing my body into a woman’s, though I have friends who are doing that and others who are changing in the other direction. They take hormones, have surgeries, the whole nine yards.

But what I have been experimenting with is changing my appearance in other, less trabzon escort extreme ways. I’ve been waxing and shaving my body almost completely, though honestly I don’t have a lot of body hair to begin with. I’ve been using some subtle makeup, and I’ve been wearing both what might be considered women’s clothing to go out in and some things that are definitely sexy women’s clothing. I wear those things when I’m alone or with a lover. One of the curious things about it is that when I wear what would be considered very sexy clothing I do feel really erotic, kind of transported to a realm of deep pleasure that I don’t experience at other times. I know that sexy lingerie is considered sexy for a reason, but I had no idea how it made the person feel who put it on…

I know this is a lot to take in Dad, are you OK with me saying these things to you?”

I took a glance over at my son. I looked into his questioning, almost pleading eyes. He is such a caring, beautiful person I thought. How could I question what he cared so much about? What kind of a father would shut out his son? I always knew him to be a loving, sensitive boy, that great balance of male and female. He surely embodies the evolution of the species that he speaks of.

Looking at him is always such a pleasure too. Not only does he exude joy and warmth, he is also really gorgeous. And as I glanced at him I could see that he had some very subtle eye shadow, mascara and lipstick on. Just enough to highlight his blue-green eyes and the deep olive skin he inherited from his Persian ancestry. Not knowing him you probably wouldn’t even notice it.

“Jeff, I love you. Your happiness is what I really care about. If you feel strongly about this and find it fulfilling, I’m there with you, never doubt that. As you say, it may take a bit of getting used to as we go along, but I am happy you’re here.

I’m wondering, in terms of your sexuality, do you consider yourself gay? Are you attracted to men?”

“Well, I have been sexual with both men and women Dad, and I’ve enjoyed both. I find that I look at the women more as I walk down the street, they can be such beautiful flowers. Though the sex with men, especially when I play the more receptive side, is so powerful for me. I guess I’m just sexual!” he laughed.

After a brief silence Jeff continued, “So, thinking about this summer Dad, I was hoping that I could wear some of my women’s clothing around the house. I know that’s a lot to ask and you don’t have to answer right now. It’s just that I don’t have as much freedom in the house I’m living in now and I’d like to explore the freedom of wearing whatever I want for a change. What do you think?”

“Hmm…I think that would be OK son. When it happens I guess I’ll see how I feel and we can take it from there.”

Jeff looked over at me with tears welling up in his eyes, “You can’t know how much that means to me, Thank you Dad”, our hands meeting and holding each other.

The rest of the ride passed with our usual banter about friends, his teachers, movies, books, and the like. We were back in our driveway before we knew it. Jeff was thrilled with his room all readied and the flowers I had put there. After a small snack and some tea we were ready for bed.

“Good night honey, please feel free to dress however you’d like around the house. I’m so glad that you’re here.” I said, as we hugged and kissed each others cheeks.

Lying in bed it was hard to get to sleep. The thoughts about what Jeff had said kept tumbling around in my mind. I was proud of him for stepping out for what he believed in, but was this going to make life a lot harder for him? Or had the culture changed so much, so fast, that the way he wanted to express himself would be seen as perfectly acceptable over a few more years?

More than that there was my own activity of late. Well, to be honest, for the past few years. As sex with Laura had been diminishing over time I had been left feeling extremely horny. Of course this is a typical story, I had started masturbating more often and watching more porn, what else is new. I had also noticed how attracted I was to porn that involved sexy lingerie, especially when men were wearing it. To see a man with stockings, high heels, panties, and garters on was becoming a real turn on for me. And it was hottest for me when that man was being fucked from behind by someone else who was dressed in lingerie. I couldn’t explain to myself why this was such a turn on, but it was, so I simply gave over to it. Of course that got me interested in the lingerie that was in my immediate vicinity.

My wife, as I said, was a conservative woman. One of the things she did like however, was high quality lingerie. Maybe that goes along with being conservative in a certain way? It was mostly lacy and silk or satin. Her stockings were classic with a seam up the back. She loved garters. She had bikinis and thongs. She had bustiers, camisoles, basques, all of the finest quality.

As you can imagine these items began to draw me closer. I started going through her drawers uşak escort when she was away, touching, smelling running the material across my skin. It all smelled so good from the lavender cachet she would put in there. And then the fateful day when I got up the nerve to try on the panties. They were red satin bikinis and on their way up, even half way up, I knew this would be a lifetime longing. I started getting hard as the satin caressed my balls and held my shaft snugly. They were just a bit small, but not a bad fit, though they couldn’t contain the response I was having to their presence, especially given my size. The tip of my now hard cock was emerging from the panties. I went over to the full length mirror on the wall and admired the view, one so familiar now from the sites I had been seeing on the web. I thought that I actually looked quite good, my body trim and in good shape, my body hair sparse and close to my skin color. Looking in the mirror it was like looking at someone else’s body. The scene got me harder the more I stared and began stroking myself through the satin barrier…

Since then it’s been hard to stop wanting to dress like that when she’s away, so I’ve given up trying. I’ve used her high heels, makeup, the works. So… how ironic, perhaps fitting it is that my son is feeling the same things. Good for him to be able to express it! For myself there remains that layer of shame that can envelope me. The hiding out, the secrecy covering it. Perhaps we will both learn some things this summer. I vowed to come clean, so to speak, at least with him. I know I can trust him, as he can trust me.

The next morning I was up early so to prepare breakfast for the two of us. The sun was streaming in through the sliding glass doors that opened out onto the pool. It was going to be another hot one today. I don’t like too much air conditioning so I keep the temp up at about 78-80 degrees. That lets me wear just shorts and a t shirt, less if I want to.

I had the omelets ready to go into the pan when Jeff came downstairs. Seeing him took my breath away briefly. He looked so good and so sexy. He was wearing some very short and tight cream colored shorts that barely covered the curves at the bottom of his lovely round ass. The white top he had on had on had spaghetti straps over his toned shoulders and came only half way down his torso, allowing his very fit belly to be seen in it’s glory. His skin is so perfect, so smooth and silky, nary a blemish to be found. He was again wearing some makeup, today a bit more pronounced. His dark hair was short and obviously done at a salon where they knew what they were doing.

I was a bit gob-smacked with this view and could barely speak at first. It was a good thing he seemed relaxed and natural. I had to work to compose myself.

“Good Morning Dad!” he cheerfully greeted me. “How’s it going?”

“Really good Jeff, I’m about to cook some omelet, I figured you might like one.”

“Absolutely, I’m famished. I slept so well in that old bed of mine, it still feels good.”

“Fantastic, I was hoping it hadn’t lost it’s touch. So what are your thoughts about what you’d like to do today? I’m up for anything.”

“After I dig into this breakfast I’m thinking of going out for a short run before it gets too hot. Then I’m also up for anything! Probably something indoors and maybe a dip in the pool?”

“That sounds great honey” I replied as I finished cooking.

After Jeff returned from his run and took a shower he came down to where I was sitting outside near the pool. He was wearing a short floral yellow and purple summer dress that was fitted enough to just cling to his belly before flaring out. He was about 5’10′” tall with fabulous long legs and, I noticed now, some pink polish on his toenails. He looked great in the dress. Seeing such a pretty, sexy person in front of me, who was also my son, had me both getting hot and perplexed. I felt the heat entering my cock and balls as I gazed upon him. I realized when I crossdressed that when both guilt and lust were present, it was the body and the lust that ruled the day as time went on and the heat arose.

“Hi Daddy,” he greeted me. as he approached.

“That’s a very pretty dress.” I commented.

“Why thank you kind sir!” he exclaimed, doing a mock curtsy while holding the sides of the dress.

We got some iced tea and again sat down under an umbrella near the pool. After some small talk I started in.

“Jeff, since you were so honest with me yesterday I thought I should be honest with you about something that’s been going on for me over these past years. And, just as you were concerned about what my reaction would be, I’m also a little nervous about what yours will be.” I began.

“Daddy, I love you. Please know that you can say anything you want to me, you don’t need to worry about how I’ll react. I’m figuring you won’t tell me that you’re a serial killer, I might be taken aback by that, so…what is it?”

“Well, over the past 3 or 4 years I’ve taken my own interest in some of what van escort you’ve been speaking about and doing, but for me it’s been very secret, closeted you might say. To come right out with it, I’ve been secretly wearing lingerie when no one is around. I started getting interested in seeing men dressing and having sex on line and at the same time I started putting on the lingerie that your mother has in her collection. For me it’s very sexually stimulating.” My voice quavering as I said this to my son, I paused.

“Wow, Dad, it is pretty amazing that we’re both going through this type of thing at around the same time, though it sounds like in different ways. I’m sorry that it has to be so secret for you Dad. That’s really too bad.

In terms of being shocked, well, I’m surprised but not shocked. I’ve been around people lately who are revealing themselves quite honestly and it’s amazing the variety of things people are into. So, no I’m just glad you felt like you could confide in me. It must be lonely otherwise.

Is this something that you feel you could tell Mom about?”

“Well, right at the moment it doesn’t feel that way. There’s too much shame involved and I’m afraid of what that would mean for us. You know I love your mother very much and I wouldn’t want to do something that would endanger our lives together. As you know, she’s a bit conservative and I think this would just freak her out. Of course, living with a secret does put some distance between us, though I don’t tell her everything in any case. For instance, I wouldn’t tell her all my sexual fantasies, that would just seem cruel, and she probably doesn’t tell me all that she’s thinking of. It’s a tricky area for couples in any case.”

“Hmm… I don’t mean to pry Daddy, but would you tell me some of the fantasies that you can’t tell Mom? And you really don’t have to if it’s too embarrassing for you.”

“Well, the most exciting thing for me is the image of two crossdressing men making love. When I envision myself as the passive partner I’d have to say that is the most stimulating.”

“So, and pardon me for my language, but you see yourself being fucked while you’re dressed in lingerie?”

“Yes, I think that’s it. Though sometimes I’m the one doing the fucking when I envision a beautifully dressed man who wants it badly.” I responded.

“Well, that’s not far off some of my fantasies Daddy. It’s also some of what I’ve been doing. But, tell me, how does this work for you on a practical level. Does Mom’s lingerie work for you? It seems like it might be a bit small.”

“Well, some of it is, but I make do since that’s all I have access to.”

My son then made a fabulous suggestion, “I’m thinking that since Mom is away and I’m the only one around, you might be able to expand your horizons here. In fact I know of websites where you can buy sexy lingerie that is made for men. We could pick some out for you together and have it delivered here. They’re very discreet in the packaging if you’re worried. In fact I’m wearing some lace panties I got on line right now.”

Jeff got up from his chair and lifted the hem of the dress he was wearing to expose the pink lacy panties he was wearing. He looked so hot in them, with his perfect belly and legs. The front had a pouch for his cock, caressing it. He spun around so that I could see the way the lacy material held his gorgeous round ass. And he was so matter-of-fact, so innocent about it all. My mouth went dry at the site.

“What do you think Daddy, do you like my panties? Would you like some like these so that we could wear them together?”

“Ohh…Jeff…they look fantastic on you…so sexy…” was all I could say.

“Well then, let’s go to the computer and place an order Daddy. Would you like that?”

“Very much Jeff, let’s do it.” as I followed his sweetly sexy tush toward the house.

Soon we were set up next to each other on the window seat in the living room with Jeff’s laptop open on the table in front of us. He began to guide me through a series of sites. Some that had lingerie made for men, both company websites and individuals who made the items by hand. It was amazing how many sites there were. That there are so many made me feel somehow better. Just knowing the number of men who must be interested in crossdressing to allow all these sites to be in business was somehow a relief to me.

It was also very stimulating to me, seeing these male models in lingerie, with their very sexy bodies. One site in particular had extremely hot men in very sexy panties, corsets, garters, stockings and more. Of course I naturally started to get excited and I could feel myself stiffening. Being so close to Jeff, our bare legs touching, enhanced the effect. When we saw an item that was particularly hot he would unconsciously, or so it seemed, squeeze my leg in excitement saying, “Ohh…Daddy look at that!”, and I would put my arm around his waist as we leaned in toward the screen and it’s delights. My cock was getting very hard as we continued to look at the pretty items and men in front of us. I knew that Jeff was also getting hot as he now kept has hand on my thigh, his upper forearm beginning to move closer and closer to my hard shaft. I think both of us knew at that point that if we went any further we would have crossed that line.