Garage Sale Sissy

I was a closet crossdresser ever since I was a young boy, then into my teens and adulthood. I always tried to hide and deny it, even to myself. I would collect a small wardrobe gathered from wherever I could and then end up feeling guilty and ashamed about it and toss out my small wardrobe. But the process would start all over again. I guess, once a CD always a CD. I even survived my fetish through several relationships and two rather bad marriages, afraid to have my partners find me out. As much as I desired it, no woman had ever found my addiction to female clothing something they were attracted to in a man.

After my second divorce, I felt very alone and women's clothes were my comfort, always finding them very soothing to me. I enjoyed the soft fabrics against my skin, especially nylon stockings and panties. They felt even better to me after I began shaving my legs and crotch area, something none of my ex's would have ever understood. But I felt silly, even at home without a dress or skirt, a bra and high heels to complete my womanly feel and look. I wasn't good with make-up, but I always added lipstick when I dressed, always privately and in secret at home. Even just an evening at home, watching TV alone, it felt good to me to be wearing my female clothes, sipping a glass of wine, and hearing my high heels clacking against the tile floors in the kitchen. Something none of my past female partners would have ever understood.

The desires in me grew stronger and I wanted another wardrobe. It's just something I couldn't seem to resist over time and especially now that I was on my own again. Buying new women's clothes are expensive and being a male, I couldn't really try them on in stores. Ordering online would still be expensive and clearly, I wouldn't even know if they would fit. I searched around my house to see if any of my ex's may have left anything behind. Most of my ex's were too small for anything to fit me anyway. Thrift stores still proved awkward for me, although they were my best choice. I always felt I was being watched, given strange looks, stared at, or thought of as a pervert of some sort. Holding up women's clothes that looked to be my size brought on all kinds of odd looks from customers and store personnel. It embarrassed and humiliated me, even if I really wanted to buy some of the clothes and shoes. Besides, I couldn't try things on there either and the store had a "No returns" policy. I managed to sneak a few things into my more manly purchases at places like Target and Walmart, slipping a few panties and packages of pantyhose and nylon stockings among household items I was buying, but sometimes young female cashiers would still look at me with strange smiles or leering glances making me feel uncomfortable. These small purchases weren't really enough for me.

One day, browsing a local thrift newspaper I came across a garage sale ad that included "Many women's clothes, dresses, tops, skirts, slips, mostly sizes 14-16, XL and 2 XL; ladies shoes size 10, some new and used undergarments including bras and panties, all in nice condition; ladies' jewelry, wigs, and more." I was immediately interested in this ad and grew hard in my pants as I read it! Knowing the sizes would be nearly perfect for me, I wanted to see this woman's collection. The address wasn't far from me, at a storage unit, listing it on the second floor. The sale would start tomorrow from 8-4. I was nervous but knew I had to go and maybe discreetly tell the woman I was "shopping for my wife."

I wanted to be early, possibly for the best selections of what she had. But arriving early wasn't perhaps exactly the best idea. All the "early bird" shoppers, all women, were already there and picking over things. I sort of sheepishly walked around looking at the woman's clothes. She had racks of clothes pulled out into the hallway of the storage unit and tables set up inside. Some of the women shoppers left but 2 or 3 were still milling around. The woman running the sale, a black woman (I'm white) who looked to be in her mid-fifties, around my age, came over to me and quietly said, "Hi, I'm DeeDee, or call me Dee. That's my friend, Bianca (a Mexican woman), helping me. Some of these clothes are hers too. Is there anything special you're looking for?"

"I, umm, I'm just doing a bit of shopping, maybe looking for some things for my wife." I looked down at my hand and remembered I no longer wear a wedding ring. Dee looked down at my hand too and I tried to cover it up.

Dee smiled, knowingly, I assume, that I wasn't shopping for my wife, and politely said, "That's fine, Hon. Take your time. If you see anything you think she would like, I'll put it aside for you."

I didn't know how this was going to work but I was interested in many of her items she had for sale. Her prices were all very reasonable and even if they didn't fit, I could donate them to the thrift store anonymously and not be out very much money. I picked out 4 dresses, 3 skirts and 3 tops. I wanted to look at the lingerie and undergarments table but was too nervous to do that. The other shoppers had left, and I was now alone with the two women, but I had no idea when other shoppers might walk in. Dee noticed how nervous I was and said, "Hon, I know you're not shopping for your wife, are you?"

"Umm, no, I guess I'm not."

"You don't have to be nervous around us. We're glad you're here and finding some of our clothes that you like. Bianca and I have both lost weight and these no longer fit us, but they look like they will fit you and my guess is that's why you came to our sale. Am I correct?"

"Umm, I guess so, yes."

"Please don't feel embarrassed. I understand that you cross-dress now, and you don't have to hide that or feel ashamed around us. I have an idea. Since it's hard for you to shop with customers coming and going, let me set some of these things that you like aside for you, and you can come back after we close up at 4 and try things on. Here, in private, just with Bianca and me. There's no judgement. You won't need to feel embarrassed or ashamed."

"Oh, my, are you sure that would be ok?"

"Yes, I'm sure or I wouldn't have invited you. You can look at the intimates table too...the lingerie and panties. You can try them on too. Some are used but they are all very clean and sanitary. We have some used bras too and several packages of new hosiery. We want you to enjoy your shopping experience with us and not feel embarrassed about wearing our clothes. You look like you should fit into most of our things."

"That's so very kind of you. I appreciate you understanding. There aren't too many places for me to find a wardrobe."

"Will you be interested in our shoes too? Most are size 10, a few are 11's. Will that work for you? We have a few flats, but most are low or medium high heels. What is your preference in footwear?"

"Oh, Dee, yes, shoes too. I do hope it's ok to admit that I like wearing heels."

"Of course, it is. They really compliment many dresses and skirts and flatter the legs. Especially with shaved, smooth legs and nylons. I assume your legs are shaved? Why don't you pick out a few pairs now that you'd like to try on later and we'll set them aside for you before any other customers come. I can always set them out again tomorrow if you don't want to buy them. What's your name, please?"

"Rick," I told her.

"Ok. Ricki, go take a quick look at the shoes and we'll see you back here at 4?" She changed it to Ricki; I suppose to give me a more feminine sounding name.

"Yes, thank you." I quickly grabbed 4 pairs of heels and set them off to the side. There were more I wanted to look at but thought I should leave some for other customers and just hope they might still be available when I got back.

I was nervous and excited the rest of the day. Waiting until 4 seemed like a week. I got back around 3:45 and waited in my car until 4. When I got back to the second floor Dee and Bianca were just finishing up a sale with another woman. As she left, Dee said, "I'm glad you came back, Ricki. I was pretty certain you would, but I knew you were so nervous earlier that I wasn't sure. I can't close the overhead door while we are in here but its fairly private behind the clothing racks in the back. Do you want to take your clothes off and put on panties and nylons first?"

"Oh, my, really? I thought I might just try the dresses over my clothes."

"Ricki you can't tell if they fit like that or how they really look, and panties are the proper undergarment. And you'll have to wear nylons to try on heels."

I hung my head shamefully. "I suppose you're right, Dee."

"I told you this would be private after 4 with just me and Bianca. There's nothing to be embarrassed about. You came here to try on and buy our clothes. I told you we'd have panties, lingerie, and nylons for you here too, along with the dresses and skirts you already picked out earlier. I have an open panty garter-girdle you can start with. Take your clothes off Ricki, and I'll help you with it."

There was a makeshift changing area the women had set up for customers to try on their clothes. I shyly undressed completely behind a rack of clothes and Dee unabashedly brought the garment to me as I stood naked with a raging hard-on! She didn't act the least bit surprised and bent down and held the white panty girdle open for me to step into. Dee said, "There's no need to feel any shame. I expected you to have an erection. Ladies' clothes excite you. That's why you're here."

Bianca came around the side of the clothes rack to watch Dee helping me dress. In a way, this has always been my secret desire. To have a woman accept my crossdressing. I always wanted one of my ex-wives or partners to share in my fetish with me and allow me to be feminine with them. That just never happened and now I was with two women, naked and trying on their clothes with them. It seemed like they accepted me and wanted me to live out my desires and feel feminine.

I stepped into the girdle and Dee brought it up around my waist and hips. It fit nice and snug like it should. Dee pulled a little strap on the back to tighten it more. With the open panty style, there was no covering my erection. Four garter straps hung down over each of my legs. Dee told Bianca, "Bring me a pair of the new nylons, the nude ones." Bianca opened the package and stretched out the fresh nylons in front of us. There were seems up the backs of the legs. She handed one to DeeDee and she rolled it getting ready to slip it over my toes.

"Point your toes and make them tight," she told me. I lifted my right leg so she could start it over my toes. Dee said, "You'll love these. They are the old-fashioned type that require garter straps to hold them up." She attached the four straps to my nylon, two in front and two in back on one leg, down around my thigh, and then did the same with the nylon on my left leg.

There was a full floor length mirror next to us in the little room area she had set up. Dee said, "Step over here and take a look. I have these stockings in black shimmer, taupe and dark brown too, if you like how they look and feel. The nude ones look nice on your shaved legs."

I stepped over in front of the mirror. I was amazed how good I felt and looked in the girdle and stockings. Dee kneeled and straightened my stocking seems. Neither of the women seemed distracted by my obvious boner. They were looking at my girdle and stockings. Bianca said to Dee, "Have him try that look with heels and bring me the 3" red pumps." Dee brought over the heels, and I slipped my feet into them, looked again in the mirror and pre-cum leaked from my penis. I almost came. Standing in front of two women wearing just a girdle with garter straps, back-seamed nylons and red heels was almost too much for me.

Dee went over to a table and brought back a white bra and held it out for me. I didn't hesitate to hold out my arms and Dee attached the clasp in back and adjusted the shoulder straps.

Dee asked me, "Ricki, you're looking lovely. How are you feeling?"

"Umm, still embarrassed, but I feel wonderful...sexy and feminine."

Dee said, "You need a panty, Sweetie. You do love panties don't you, Ricki?"

"Umm...mmm...yes."

"Most sissies do. Let me bring you one of my used panties. You don't mind them being used, do you? By a black woman?"

I was surprised when she casually called me a sissy.

"Oh no, Miss DeeDee. Not at all. If you don't mind me saying so, I love that you had worn them, pressed up against your...well...your, you know, your..."

"My pussy. You can say my pussy."

"Yes, worn them against your pussy."

"Here's a red nylon spandex blend panty. I wore these a few times. I think you will like how they feel against your penis. And look nice with the red heels."

DeeDee bent down held the panty out for me to step into. I loved the feeling of being dressed so femininely by these two woman, practically strangers to me. Dee acted as though my hard-on was nothing unusual and just pulled the silky panty up over it. I let out a little moan under my breathe as the smooth silky panty felt so good around my cock and balls, and over my ass. DeeDee's hand brushed ever so slightly against my erection. I wasn't sure if she did that on purpose or not, but clearly these two women enjoyed their teasing and embarrassing me in a very sensual and erotic way.

Bianca said, "Let's have him try a slip and the red dress he picked out earlier."

When Dee brought the slip down over my body, I got goose bumps and squirmed as the silky material brushed over my body. My cock still hard, I tented out my panty and made a slight "bump" in the front of the slip. Bianca brought the red dress over and held it out for me to step into. DeeDee zipped me up in back and the women guided me over to the mirror again.

Dee said, "Sweetie, you look lovely. Do you like the color and fit?"

"Yes, very much. It's a very exciting feeling for me. You ladies are so wonderful and understanding."

DeeDee smiled and asked me, "Ricki, what do you do when you're dressing and wearing the clothes?"

"Umm, well, I never go out if that's what you mean. I wear the clothes to sort of soothe and comfort myself. I like to get a glass of wine and just watch TV when I'm dressed."

"And you're hard like you are now?"

"Yes, almost always."

"So, then I assume you masturbate while you're dressed?"

I was somewhat surprised by her questions, but I answered, "Umm, yes."

"You don't have to feel ashamed to admit that. The clothes feel sensual and sexual to you. You no longer have a wife or partner, so you hide alone at home, dress up like a sissy and masturbate. Am I right again, Ricki?"

"Umm, well, it's hard to admit, but yes."

"Yes, what, Ricki?"

"That I dress up in women's clothes and masturbate."

"It's nice to unburden your secrets and have someone to tell them to, isn't it, Ricki?"

"Oh, geez, yes! I'm sorry, you're making me so hot right now."

"Do you watch yourself masturbating in front of a mirror, Ricki? And wish a woman was watching you?"

"Omg, yes!"

"And you know that is very sissy behavior for a man? To dress up in women's clothes, like you're dressed now, and masturbate?"

"Yes, I know it is."

"You're a very submissive man aren't you, Ricki?"

"I suppose I am."

"And you like to take directions from women. You like to be obedient for them. It excites you."

"Yes."

"I want you tell me that you're a sissy, Ricki. Say it out loud. Admit it and to me and Bianca."

"That's so hard, DeeDee. It's so humiliating for me as a man to say that."

"But you're not a man are you, Ricki?"

"No...not really."

"Don't be afraid now, Ricki and tell us..."

"I'm...I'm...I'm a sissy."

"There, that's better, isn't it? You've wanted to say that to a woman for long time, haven't you Ricki? Say it again, Ricki."

"I'm a sissy."

"This is the first time you've been able to feel feminine around women, isn't it? You like being called a sissy, don't you? You like telling us you're a sissy."

"Yes, I'm sorry."

"Don't be sorry. There's no need to be sorry or feel ashamed. Some men like you are sissies. And you love panties? Sniffing them, smelling them, wearing them?"

"Oh, my, yes...I do."

"Ricki, have you ever masturbated in front of a woman?"

"Oh, my, no, Ma'am."

"Would you like to masturbate now, while Bianca and I watch you?"

Bianca didn't wait for me to answer. She moved around behind me and lifted my dress and slip up and held it up around my waist.

DeeDee said to me, "It's ok, Ricki."

"Are you sure?"

"Yes. It's private. Just with Bianca and me."

"Oh, my...I'm so nervous! I feel ashamed to do this."

"There's no reason to feel ashamed. Do you want to do it in your panties? Or pull them down?"

"Oh, DeeDee!"

"Just tell me what you want."

"These panties feel so good."

"Tell me what you want. I know the panties excite you. Do you want to cum in my panties?"

"Yes!"

"Yes, what? Tell me."

"I want to cum in your panties."

"What a good boy. I knew you would want my panties. That's so sweet. Kneel down Ricki. Kneeling is very respectful and humbling in front of a woman. Jack-off in my panties for Bianca and me."

I realized what I had just said to DeeDee and how ridiculous I must have sounded and looked to the two ladies. Kneeling in front of DeeDee, Bianca holding up my dress, my panties exposed, stockings attached to garters, red heels...and telling DeeDee I wanted to masturbate in her silk panties!

"Go on, Ricki. Jack-off and cum in my panties." I started masturbating in DeeDee's panties, rubbing myself up and down, the silky material feeling so good. She watched my hand massaging my encased penis and balls and said to me, "How would a sissy white boy like you like to buy my black-pussy freshly-worn, dirty, wet-stained panties to jack-off with?"

Omg...I came hard.

I made arrangements to buy DeeDee's and Bianca's dirty panties once a month from then on.