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Relationship With Crossdressing - Family Matter
🕑 Added 2025-04-04 15:15:05 +0000 UTCThere is nothing sexier than a pair of beautiful, shapely legs in sheer stockings under a short skirt with a little lace showing at the hem, all perched on a pair of beautiful high heels.
Well, maybe with the exception of a beautifully shiny, long, flowing mane of hair, a beautifully made-up face, and a pair of beautiful, ample breasts peeking out of a sheer top or lacy dress. These things are what I find sexy.
It doesn't matter to me who is underneath these things, be it a woman or a man; I love it regardless.
By the way, my name is Tommy, and I am a lifelong cross-dresser. Debbie and I have been married for ten years, and although she is aware of my dressing, I always felt that I had managed to keep it a well-guarded secret from everybody else, at least until recently.
Even though my wife has known me for years, she has never openly participated in that side of my life. Debbie gives me my "girl time" as long as it stays at home, but she has made it clear that if anyone else found out about my "girl time," she wouldn't hesitate to leave me.
I only have a small wardrobe, with two skirts and blouses that I can mix and match, several pairs of panties, a couple of bras, and a full slip. My favorite, though, is a matching pink lace bra and panty set and a floor-length satin nightgown.
Even though I have only dressed for myself and have never been out as a woman, I still try to work out and stay fit. It helps my self-esteem, even if I am my only audience. As a man, I have never been what would be considered macho, but I'm not effeminate, either.
But when I dress, I can at least appear as an average woman with a slim body. Debbie's mother, June, lives about an hour away from us, so we see her on a fairly regular basis. June is widowed and really doesn't have any other family nearby to keep her company.
Because of this, June and Debbie have become much closer since Debbie's father passed away several years ago. It's not unusual for Debbie and me to spend the weekend at June's home or at least meet June for lunch or dinner. On the other hand, June seldom comes to our home, and she almost never comes without calling us ahead of time. June, however, does have her own key to our home, as we do to hers.
Everything seemed to be just fine until last month. Before I left for work one morning, I decided to wash my lingerie. As I have done on numerous occasions, I put my things in to wash and left for work.
I don't have far to go to work and often come home to have lunch. Usually, I'll put the clothes on, go to work, come home for lunch, and dry my clothes while I eat. Then I'll put the clothes away before going back to work.
On this day, however, when I came home for lunch, June was there. I wasn't too alarmed when I saw her car in the driveway until I walked in and found June had dried my lingerie and was neatly folding it on our bed. I'm sure that I was white as a sheet when I walked in and saw what she was doing.
I said, "June, what are you doing here? You shouldn't have to work doing our laundry when you come down here. I'll take care of it." June said, "Oh, I don't mind. I like to help out." She wouldn't let me take over the folding of the clothes; she just kept folding them. She had a wicked little smile when she said, "Did Debbie get some new lingerie?"
Now, June is one of the most intelligent people that I know, and she is well familiar with Debbie's lingerie, both in preferred styles and size. Debbie is larger than I and tends to go for comfort rather than the erotic. I tend to prefer lacy, sexy things. June had to know that the lingerie she was folding was not Debbie's. I know I must have gone from ghost white to bright red in record time.
All I could manage to get out was, "Ah, I don't know, I guess so." I was so scared. The only thing I could think about was June telling Debbie, and Debbie kicking me out. Nothing else was said about the incident.
When June was finished folding my clothes, I put them away while she was in the other room. I went back to work but couldn't really concentrate on anything except what would happen when Debbie got home and talked to June. Surprisingly, nothing was said about the clothes that night, and the three of us had a rather normal, pleasant evening.
I thought I was home free, although I kept noticing June gave me wry little smiles now and then. She had to know the lingerie was mine.
But why hadn't she said anything? Well, everything went quite smoothly over the next month, with no indication that June had said anything to Debbie or even that June knew the clothes were mine. One day at work I was moving some old boxes of files to a storeroom. When I reached down and tried to pick up the box, it was heavier than I had realized.
As I stood up with the box, I immediately felt a sharp pain in my lower left abdomen. I dropped the box and saw the files scattered all over the floor. Just then, I really didn't care about files. I needed a doctor, but not to tell me what was wrong.
I knew very quickly that I had a hernia. I hobbled to my boss's office and told him what had happened; he then drove me to my family doctor. While I waited for them to work me into their schedule, I called Debbie on my cell phone to tell her where I was and why.
Debbie was at the doctor's office before they got me in, which wasn't hard. It seemed to take forever. But, then it always does when you're in pain. When I did finally get back to see the doctor, he confirmed what I already knew, except that he did seem to be a bit more concerned than I would have expected from just a hernia.
He immediately made an appointment for me with a surgeon he recommended for the following day. The doctor wrote me a prescription for pain medicine, which we had filled on the way home.
Debbie called June and told her what was going on. June, of course, was sweetly concerned. That night was rough but bearable with the pain medicine. The following day, Debbie took off work and took me to see the surgeon. The surgeon told us the tear was fairly large.
He was concerned that the intestine might prolapse, sticking out of the tear and, in effect, blocking the intestine. He had me admitted to the hospital that afternoon and had my surgery scheduled for 7 am the next morning. The surgery went fine, so I'm told. I was a little out of it. The doctor actually implanted a small mesh screen at the site of the hernia to keep the intestine in place and to help prevent the healed incision from ripping apart.
Late that afternoon, I was taking a few steps and was doing well enough to be sent home. They just don't keep you very long anymore. When Debbie and I got home, I ate a little soup, took another pain pill, and went to bed. Debbie waited on me at every turn. She seemed to know what I needed before I did. Then I tried to sleep.
If I thought the pain was bad the other night, I had no idea. I tried to turn over in the middle of the night. The pain pill had apparently worn off. I woke Debbie up with my moan, even though I tried to stifle it.
Debbie got my medicine for me and helped me out of bed so I could go in to use the bathroom while I was awake. Then she sat up with me until I went back to sleep. The next morning I got up and walked a little.
Debbie fixed some breakfast for us. I hadn't eaten much the day before, and I was pretty hungry. Debbie and I sat and watched TV for a while. I never understood the appeal of most of those daytime shows.
Around lunchtime, June arrived. It was now going on four days that Debbie had been off work with me, and June was going to stay with me for the next few days while Debbie went back to work. We sat around and talked about the surgery and the doctor's orders, and such.
Debbie told June that I had had a pretty hard night last night. June is such a sweet lady. We get along quite well, and I feel very lucky that she is not the witch that I hear other men talk about when describing their mothers-in-law.
She was genuinely concerned that I had been in so much pain. I told Debbie and June, "It really wasn't that bad, except that it was hard to turn over without putting pressure on the incision. My pajamas don't make it any easier. They're cotton-on cotton sheets. There's a lot of drag.
If I try to raise up so that my pajamas don't drag the sheets, then raising up puts a strain on my abdomen, and it's even worse." June smiled and said, "Women don't have that problem when we wear nylon gowns and panties. The nylon just kind of slides against each other, so there is very little friction and drag. It might save you some pain. You really ought to try it."
The whole time that June was talking, I was turning whit,e and I kept stealing subtle glances to Debbie to see what her reaction was going to be.
I was quick to respond, "June, I'm a guy. I can't wear a gown and panties." June said, "Oh, so you enjoy pain? Are you a masochist? Is there something you aren't telling me?"
"No, I don't enjoy pain, and I'm not a masochist.
Debbie, help me out here."
"Actually, honey, she's right," Debbie said. "It's just a matter of being practical. I know it's not your fault, but you kept me awake some last night, and I really need my sleep tonight. I have a big meeting in the morning, and I need to be well-rested. I think we can find you something to wear later." All the while, Debbie and June were both smiling like Cheshire cats.
Debbie didn't seem to be upset at all and was agreeing that I should wear a gown and panties.
If Debbie's previous warning about others finding out about my dressing had not been burned into my brain, I'm sure I would have been ecstatic at this prospect.
I was concerned, but this was an argument that I really didn't want to win, so I told them I would try it. The conversation changed direction, and soon the ladies were talking about a women's wear shop called "Trudy's" that had recently opened up in the area.
Debbie said that they were having a grand opening sale, and some of the girls in her office had gotten some really good buys there. June said, "We should go check it out once Tommy is feeling better." They both smiled at me as Debbie replied, "Maybe we will.
One step at a time." I just assumed that they were talking about going there themselves once I was able to get along on my own. I lay down while Debbie and June fixed dinner, and after dinner we sat and watched some TV. When it was time for bed, Debbie helped me into the bedroom, where I started to get into bed. Debbie told me to wait.
Debbie went straight to the back of my closet, where I keep my few girl clothes, and she pulled out my favorite nightgown, a long, satin, hot pink gown with a lace inset at the tight-fitting bodice and a matching pair of satin panties. She began to unbutton my pajama top. I asked, "Deb, are you sure you're ok with this?"
Debbie said, "Oh, I think it will be alright. It just makes sense. It will make it easier for you to turn over, and I don't want you keeping me awake tonight."
I settled in, and Debbie stayed up with June for a while before retiring for the night herself. I certainly had a more restful night that night and a lot less pain.
I love the feeling of sleeping in a gown. Debbie occasionally allows me this pleasure. In the morning, I woke up while Debbie was getting ready for work. I managed to get up on my own and did my morning thing, and it was back to bed. Debbie kissed me goodbye before leaving for work.
I slept for another hour or so, then got up to find something to eat. I slipped on my robe and slowly made my way to the kitchen. June was up, sipping a cup of coffee. She asked how my night was and fixed me a cup. "I had a better night.
Not as much pain, and you were right, the gown did make it easier to turn over. I guess I owe you for suggesting it." June said, "Well, I'm glad I could help. I like the color of your gown. Take your robe off and let me get a better look." I hadn't thought, but my gown was clearly visible below the bottom of my robe.
What could I do? She had already seen it, and after all, it had been her idea. I stood up and took my robe off, and laid it on the back of the chair. I decided to have a little fun with it and gave her a little "tah-dah" gesture with the hands up and out. June said, "Oh, that's beautiful. A little sexy, and what a wonderful color. It fits you very well. That's not Debbie's, is it?" My gown was bright pink, and I was bright red. I couldn't answer.
I just hung my head. There was no way I could deny it, as I said before, Debbie and I aren't quite the same size. June surprised me by saying, "Don't worry about it. It's ok. I don't care what you wear as long as you continue to take care of my daughter and make her happy.
Are you wearing the matching panties?" I blushed, "How did...?" "Oh, I remember them from when I was folding your clothes last month. You have nice taste in lingerie, by the way. Let me see how they look on you."
"JUNE!" "Oh, don't 'June' me. I've seen you in your underwear before. And there's not much that can be more revealing than that so-called swimsuit you wore to the beach last summer. Come on, don't be a prude."
She was right. June, Debbie, and I had all gone to the coast last summer, and even I thought the suit was a little skimpy. But I wore it because Debbie bought it for me, and she said my butt looked cute in it. I slowly pulled up my gown and showed June my panties. "I knew you would look good in those.
Now what do you want for breakfast?" That was it. That was all she said. No questions, no judgments, nothing. She acted like it was no big deal. Like I was one of her girlfriends or another one of her daughters, and we did this all the time.
I was still a little self-conscious about the gown, though, so I put my robe back on and waited for my bacon and eggs.
After breakfast I went back to bed and only got back up for lunch and to take some more medicine. After lunch June was sitting on the couch and asked me to sit at the other end of the couch.
When I sat down, June put an old towel in her lap and helped me lift my feet to put them in her lap. I thought she was going to give me a foot massage. I lay back and relaxed. June got something out of her purse and shook it in her hand for a moment. Then she took the lid off and started to paint my toenails.
When I realized what she was doing, I instinctively jerked my feet up. Big mistake. My Darvocet wasn't nearly that good, and I winced in pain. June grabbed my feet and slowly put them back in her lap. "June, what are you doing?"
"I found this nail polish in Debbie's vanity and thought it was almost a perfect match to your gown. You're going to look so cute with your gown and your nails the same color."
I didn't remember Debbie having that color polish. It must be something new she bought, but why would she buy that color? She usually preferred reds or French tips.
I said, "June, I don't think this is a good idea. Debbie won't like it." "The heck with Debbie. If she doesn't like it, she can change the color to one that she likes when she gets home."
"That's not really what I meant." "I know what you meant. Don't worry about Debbie. Besides, since you're recovering from surgery, I can take you now. If you try to fight me, you'll just end up hurting yourself again.
So sit back and relax." June was smiling, and I knew she was joking about me fighting her. She knows I would never physically fight her, and June usually gets what she wants anyway.
I decided not to argue with her. I had never really liked the smell of polish when Debbie had done her own nails. But now that it was my fingernails that were being polished, it didn't seem that bad. In fact, it was almost intoxicating. I had never delved into makeup or polish before.
When June was finished with my toes, she grabbed my left hand and started on my fingernails. When I started to say something, June gave me a stern look and simply said, "Hush!" I certainly didn't want to jerk away from her again and risk that pain. I could do without that, and I could always remove the polish later before Debbie got home.
Before long I was sporting bright pink nails, fingers, and toes that matched my gown pretty closely. I was mesmerized by the bright nails. They were just beautiful. June and I talked and laughed for quite a while, just like two girlfriends. All the time we talked, I kept looking at my nails.
When I grasped my coffee cup, when I took my medicine, or anything I did that caused my hands or feet to move, my eyes were drawn to my nails.
After a while, I went back to bed. I had just taken some pain medicine, and I was asleep in no time. I only woke up when Debbie came in and sat next to me on the be,d and put her hand to my forehead to see if I had any fever.
As I became more awake, I realized that my hands were outside the covers, visible to Debbie, and I had not taken the polish off yet. I thought Debbie would be furious. The only thing she said was, "Tommy, that's such a pretty color.
Did you do your nails yourself?" I blushed and meekly said, "No, Debbie, I wouldn't paint my nails, especially with June here. Your mother did this for me. I had planned on removing the polish before you got home, but I guess I slept too long. I'm sorry, honey. I'll go into the bathroom and take it off. I was shocked when Debbie said, "Don't bother; since Mom did them, you might offend her if you remove it. I assume she saw your gown also?
"Most of the time I could get a pretty good read on Debbie, but this time I couldn't read her at all. I didn't know if she was really pissed and hiding it well or what was going on."
June picked the polish. She said it matched my gown." Debbie said, "Well, she was right. It is a pretty close match. How are you feeling today? "I'm starting to move around better". I'm not ready for a footrace yet, but I'm doing OK."
"Good. Let's look at the incision and see how it's healing. Pull up your gown." I thought, '"Pull up your gown." Now, that's a phrase I never thought I would hear my wife say to me'. She said the incision was healing nicely. I mentioned to her that it was beginning to itch. The nurse had shaved part of my groin and abdomen so they could do the surgery, and now the hair was beginning to grow back, and it was starting to itch. Debbie said that we might be able to do something about that tomorrow. I wasn't sure what she was talking about but didn't ask. Debbie said, "If it looks
OK, tomorrow, you can take a shower." Come on. Are you hungry? I brought Chinese. Just put your robe on and come to dinner."
Debbie started to help me with my robe, but then just looked at the robe and shook her head. She said, "This robe is so ratty. You really need a new one. Maybe we can find something at" Trudy's." For now, just wear mine."
She handed me her white satin robe and helped me slip it on. I almost lost control, taking in the wonderful scent of Debbie's perfume that lingered on the robe and the feeling of the soft robe sliding over my gown. My head was spinning, and it wasn't from the pain medicine. The white robe didn't really match my gown, but I couldn't have cared less. It wasn't like I was a celebrity and the tabloids would crucify me for not having a matching outfit.
Uh... What was that about "Trudy's"? So, with that, I went to dinner wearing Debbie's robe over my gown and my nails shining brightly. When June saw me, she just smiled but said nothing.
After dinner, we sat and watched a DVD that Debbie had brought home. Unfortunately, it was a comedy, so for most of the night I was holding a pillow against my stomach when I laughed, trying to keep from hurting.
Debbie apologized for getting a comedy, but we all enjoyed it. The following day was Saturday, and Debbie was supposed to be off. However, with her having to be off with me so much already this last week, she would have to go in for at least a little while, so she decided to go in late.
When I got up, Debbie checked my incision and deemed it healed enough for me to take a shower. Thank goodness. I had been washing with a washcloth for the last few days, but I really needed a shower.
Debbie adjusted the water temperature as I took my gown off. I got in and washed my hair. Just as I was starting to soap my body, Debbie stepped into the shower with me. She took the soap from me and started to wash my body.
As she washed my body, she also began to fondle my cock and balls, and I was quickly hard as a rock. She was very passionate, smothering me with kisses and massaging all over my body.
At first I didn't see her pick up the razor. She smoothed her shaving cream all over my legs and then started removing all my hair.
When my legs were free of hair, she started on my chest, then under my arms, etc. She didn't stop until I had no hair below my eyebrows, including a fresh shave on my face. That took care of the hair growing back around my incision and itching, at least for a few days. It was such an incredible feeling I wasn't about to stop her. And she kept me hard the whole time.
When she had finished the shave, she dropped to her knees and took my hard cock in her mouth. I was in heaven.
It was so erotic to have my beautiful wife drain my cock while she ran her hands all over my now smooth body with the water bouncing off of us. When the water ran cold, we decided that it was time to get out of the shower. As I dried off, I couldn't help running my hands all over my smooth body.
I had never shaved my body before, and this was very exciting. Debbie rubbed a perfumed lotion all over my body, then gave me a fresh pair of panties and one of her clean gowns.
The satin gown sliding over my now hairless body was wonderful. Debbie handed me her satin robe, and when she was dressed, we joined June for breakfast. After breakfast, I sat and talked with June and Debbie as Debbie put on her makeup so she could go to work. Debbie and June both saw that I was watching Debbie intently.
I had watched Debbie apply her makeup before, but I guess I was fantasizing a little. When she was finished, Debbie was putting her makeup away when she said, "Tommy, your lips are chapped. Come over here."
As I stood in front of her, she took her lipstick and coated my lips, then handed it to me, saying, "There, that's better. Keep that on your lips. It will help protect them, and it matches your nails." After Debbie left, June and I talked and watched some TV.
I didn't realize that I was rubbing my lips together, feeling the lipstick. The sight of my lipstick on my coffee cup was very sexy. June suggested I touch up my lipstick, so I did. There was a Victoria's Secret commercial that came on as we watched TV, and June commented on how pretty the bra was that they were selling.
"When I did your laundry, I noticed that you have a very pretty bra, too. Did you get it at Victoria's Secret?"
"No, it's from a small shop I found when I was away on a business trip. It is pretty and has a panty to match.
I love them." "Why don't you go put them on? You know it will make you feel good." When I had the bra and panties on, I filled out the cups with my foam breast forms, vowing to someday get some good silicone forms.
I watched myself in the mirror, again running my hands over my smooth body.
I was impressed that a small thing like shaving my body could do so much to make me look feminine. The smooth body, the bra and panties, the nail polish, the lipstick. Even with short hair and no other makeup, I had to admit that I was kind of cute. I went out to show June.
"Wow, you look marvelous. Don't you feel better?" I had to tell her that it did make me feel good. "I hate to cover up such beautiful lingerie, but I wouldn't want you to catch a cold. Put your gown and robe back on and come over here and sit down." I did as she asked and sat at the table as she got out her makeup kit.
She turned me where the light was better and began applying foundation to my face. Eye shadow, liner, mascara, and blush were next. Just as June was applying a deeper red lipstick, Debbie walked in.
Debbie said, "What the hell is going on?" All I could do was stand there with my red lips open in shock. I didn't know what to do or say.
I was so confused. Before the last couple of days, I knew that Debbie would never have tolerated me in makeup. But she had also been so good lately about the gown, the shaving, and the lipstick. But I still remembered her words to me about keeping my secret.
I just knew I would be looking for a new place to live. "Mother, what are you doing to Tammy?" "Honey, I'm sorry, June and I were just playing around. I'll go wash it off. It's just that... who's Tammy?"
"Oh, Tammy, it's alright. I was just trying to tell Mother that your makeup is all wrong. Mother, this makeup makes her look older than she is. Here, let me show you. Sit down, Tammy." I looked at Debbie and thought, 'Who are you and what did you do with my wife? I sat, and Debbie cleaned my face and reapplied my makeup with brighter colors and different tones.
When she had finished the makeup, I reached for a mirror to see what she had done.
Debbie playfully slapped my hand, saying, "Not yet, Tammy. 'I'm not quite finished yet." She then picked up a shopping bag that she had come in with, but I hadn't paid attention to.
From the bag she produced a beautiful, below-the-shoulder-length blond wig that she then settled onto my head.
After several minutes of pinning, brushing, shaping, and spraying, she disappeared into our bedroom. A minute later she was back with a simple gold necklace and a pair of gold hoop clip-on earrings that she placed on me. June gasped and said, "My gosh, Tammy, you are so beautiful, just like Elaine.
I have a new daughter-in-law." Ok, I was smart enough to figure out that I was now Tammy... But who is this Elaine? Debbie and June each took one of my hands and led me to the bathroom mirror.
To say I was surprised would be an understatement. June was being kind when she said I was beautiful. Cute, maybe.
But I certainly looked better than I ever thought I could. I didn't look like a guy in drag at all. I looked like an attractive young woman. The first thing that I saw when I looked in the mirror was my eyes and how beautiful Debbie had made them. My eyes were my best feature. They seemed to pop out at you. Then I took in the overall look.
I kept turning from side to side, watching the earrings move and the hair bounce around my shoulders.
Oh, how I love long hair. Debbie broke me out of my daze by giving me a hug and a gentle kiss on the lips, saying, "Happy Birthday, Tammy.
I love you." June also gave me a hug and said, "I love you, too." I finally got my wits about me as I hugged them back and said, "You two have made me the happiest girl in the world. Please don't think me ungrateful, but I don't understand, Debbie.
Why all this, all of a sudden?" Debbie said, "Let's go back into the living room and relax, and I'll explain." June fixed us all some tea as Debbie and I sat on the couch together. Debbie started to explain, "About a month ago, Mother told me that she had found your panties and things in the washer.
I was furious at first and was ready to throw you out. Mother calmed me down, and we talked for the longest time. Mother shocked me when she told me that Daddy had been a crossdresser, too."
I was stunned. "Frank was a crossdresser?" June came in and handed us our tea and said, "Frank became quite an elegant lady named Elaine a couple of times a month. Elaine and I would even go out to a movie or to dinner on occasion."
Debbie continued, "Mother told me how much fun she and Elaine used to have and how much more attentive Elaine was to Mother. She convinced me that you and I could have the same kind of fun that she and Elaine had. It did take me a while to warm to the idea, though. I had to do a lot of thinking about it, and I did some research on the net. I learned that there are a lot of couples that include crossdressing in their relationship and it actually strengthens their marriage. I decided that I loved you so much as Tommy that I owed it to us to try to love Tammy just as much. Mother agreed to help me bring Tammy out into the open." I smiled and said, "Tammy... I love the name you've given me. Wait a minute!
You two set me up! And, Frank was Elaine?" We all laughed, and June showed us some pictures of Elaine. She was very elegant.
I found myself a little jealous. Later, I modeled my meager wardrobe, and we vowed to visit Trudy's as soon as I was up to it. Well, June, Debbie, and Tammy did visit Trudy's about two weeks later, and Tammy's wardrobe started to grow by leaps and bounds.
The three of us began to have a regular "Ladies' Night Out" once or twice a month and frequent shopping trips on the weekends. Tammy is so lucky to have such understanding women in her life.
"Tammy, I saw the cutest little dress in the window at Trudy's today; I'll bet you'd look great in it," Debbie says. Well, how can I argue with that? "Sounds great, sweetheart. Just let me touch up my lipstick, and we'll go check it out."
Comments
Marie DuBois
I love this story. I can't wait for paert 2
Amanda
Yes, this is so delicious.🫠❤️
My Freeze
Loved it! What a great story. Characters are so real feeling. This has all the makings of a great serial. Look forward to more of the adventures of Tammy, Debbie and June. Thanks.
Brianna Demonet
Gosh I hope there's a second chapter!
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