Jerri is a close friend whom I have known for a long time. I was on an interview board for her when she joined the volunteer fire department. I was a little skeptical about her joining, especially since her husband seemed to be rather indifferent about it, but was overridden by the rest of the board. As time went on, she proved herself to be one of the top responders and an excellent Emergency Medical Technician. Eventually we became good friends and I even requested her as my lieutenant when I was promoted to captain. It was a very sad day for me when she and her husband moved out of town.
One day, she came to my house for a visit, unannounced. I did not hear her even come in the house. She heard the shower running but it had been a long trip and nature was calling urgently. She decided to use the bathroom quickly before I got out of the shower and figured she would say something if she heard the water turn off so that I would not get out of the shower while she was taking care of her business. Upon entering the bathroom, she saw a pair of heels on the floor, and stockings, a bra and a slip on the counter. She took care of her business and the shower was still running, but she decided to stay and confront me when I finally got out.
When I opened the shower door and reached for the towel, I saw her standing there and exclaimed "Oh No!"
"I didn't know you were into such things" she said in a disgusted voice, and left the room.
Slowly I get dried off and headed for the bedroom to get male clothes. The interest in the items I have laid out in the bathroom has disappeared. Nearly in tears, I figure that she has gone and I've lost a treasured friend. As I came around the corner, she surprised me since I thought she was gone, and gave me the familiar hug that we have exchanged many times before.
"We are still friends,” she whispered. "Go ahead and get dressed. I will wait in the living room."
With my stomach doing flip-flops, I got dressed in my standard blue jeans and flannel shirt. "I am so embarrassed" I mumble. "Not only did you see me naked for the first time, but you also found out..."
" ...that you like to wear women's clothes."
"Yes" I reply, staring at the floor.
After a very long pause, you ask "Are you gay? You've never made a pass at me and you never married."
"I couldn’t make a pass at you. You are married! And, no, I’m not gay. The idea of sex with a male is repulsive to me. If I were born with female plumbing I would be lesbian."
"But your male plumbing does work - at least I assume it does, since you were hard when you first opened the shower door."
"It works" I replied, still a little uneasy about the whole situation.
"Relax. The cat's out of the bag now and as far as I'm concerned we're still friends. If you care to talk about it, I'd like to know more. If not I understand."
"I first did it when I was 10. The short version is I had an orgasm for the first time (not knowing anything about such things) and liked it so much I was instantly hooked."
"Do you need to dress up to get aroused now?"
"No, it really doesn't take much. I can get that way by just looking at a lady with nice legs wearing nylons."
"Your secret is safe with me," you reply. "You are still my friend."
Noting my uneasiness, she steered the conversation away to a different subject. When the time came for her to leave, she went to use the bathroom and left her bra on the counter. As I gave her a hug goodbye, I didn't feel her bra strap. It didn't occur to me that she wasn’t wearing one until after she left and I found it sitting on the counter in the bathroom with a little note - "Let me know how it fits." A couple months later I called Jerri to see if it would be okay for me to stop by since I was going to be in the area. She said it would be great to see me again and I told her I would be by in about 3 hours. She told me she would have a surprise for me when I got there.
When I arrived and knocked at the door, she met me wearing a long overcoat and high heels. I was shocked when she slurred, “Come on in, the door’s open” as her overcoat came open and revealed she was wearing nothing underneath it except for a pair of thigh high stockings.
“Jerri, you’re drunk!” I gasped as I reached for her arm, noting she was a little unsteady on her feet. “I’ve never seen you like this before.”
“Yes, I am,” she replied nearly in tears. “I’m so sorry. I can’t help it.”
“What’s wrong?” I asked, wondering what was going to happen. I had never seen Jerri drunk even though we had known each other for the better part of 15 years. “What will your husband say when he gets home?”
“He isn’t coming home,” she choked. “He fucking left me about 4 months ago.”
I was aghast. I had never known Jerri to swear before, let alone use the “F” word. “I know we haven’t talked since you came by the house that day when I was in the shower. Was he gone by that time?”
“Yeah, I was going to tell you then, but the way things went that day I just couldn’t. I didn’t want you to see me cry. You were almost ready to cry yourself.”
That was for sure. I was so embarrassed when she found out I crossdressed. She had made me feel better about it before she left and I was so glad she still wanted to be my friend. She even invited me to stay for the night since it was getting pretty late. I could sleep in the spare bedroom.
I agreed and followed her directions to it, after retrieving an overnight bag from my car. The spare room looked as if it were actually Jerri’s room. The closet had her clothes in it and the dresser contained intimate items that looked like they could be hers. After snooping around for a bit I returned to the livingroom where she had passed out on the couch. Oh well, that was it for her tonight, so I went off to bed in the spare bedroom.
“Hi,” I called to Jerri the next morning. She was still passed out on the couch in the livingroom fully exposed since the overcoat she was wearing had fallen open.
“Oh my God!” she shrieked, pulling the overcoat closed. “You scared the hell out of me!”
“Relax,” I told her. “Nobody else is here. It’s alright.”
I turned my back to her as she stood then came up behind her and put my arms around her.
“What happened last night?” she asked. “I was very drunk and I don’t remember… Did we…”
“You certainly were. Are you okay now?” I asked.
“I’ve got a bit of a headache,” she whimpered “but I’m okay. I just need a shower. Did we…”
“No,” I replied. “I have too much respect for you to take advantage of you like that. All I did was look, but I must admit I liked what I saw.”
“I’m so sorry,” she sobbed. “I made an ass of myself. You are so sweet.”
“Look,” I said soothingly. “You go take a shower, and gather your wits about you. I will see if I can fix some coffee.”
She turned around, gave me a hug and kissed me on the neck saying “Thanks Bert,” then kicked off the heels she was still wearing and headed off to the bathroom.
I located the coffee, the coffee pot and a couple of mugs. I was looking out the kitchen window drinking mine, when I heard her footsteps come from behind. I turned around to see her hair wrapped in a towel and wearing a terrycloth bathrobe.
“Feel better?” I asked as I handed her a cup of coffee.
“Yes, thank you.”
We were standing in silence drinking coffee when suddenly she blurted: “You never said how the bra fit.”
I was so startled by the remark I nearly choked. “Well if you must know, it was a little tight since it was a 34A. I wore it anyway and stretched it out, but I need a 36 or 38.”
She dropped the subject just as suddenly as she brought it up and fixed breakfast. We made small talk about our past in the fire department and reminiscing about how we got to know each other and the times we had. When we were through eating, she asked how long I could stay. Since it was now Saturday, I told her I could stay for a while, but had to get home before evening.
“Would you allow me to take you shopping?” she asked.
“I want to get you some girl clothes, nylons, heels, a skirt and blouse, just to see what you look like in them.”
“I don’t want you to buy me anything,” I replied. “I already have those things at home. Besides, dressing up like that makes me very aroused.”
“I thought it did. That’s why I want to see you dressed up. I can go to your house if you want…”
“Really?” I asked shocked. “I had no idea…”
“Yes,” she interrupted. “I want to be desired by somebody who truly cares about me.”
“Well I have always thought you were sexy,” I replied, not believing where this was going. “But I value our friendship so much I didn’t ever want to jeopardize it by saying so, especially since you are married and were a co-worker.”
“I am not a co-worker anymore, I am getting a divorce, and I want you, so what are we waiting for? How’s that for being blunt?” she asked and gave me a deep lingering kiss.
My emotions were reeling. I was getting hard and somewhat nervous all at the same time. I needed some time to think. “I can’t do this in Bill’s house. It just wouldn’t be right,” I told her.
“Let’s go to your house then,” she replied. “We will both get a chance to be alone with out thoughts and cool off a little bit while we drive out there. I need to get out of here for a while anyway. All I do here is cry and get drunk.”
We agreed it would be better to go to my house, driving our own cars. I began to wonder: Had Jerri become dependent on alcohol? Was I part of what was breaking up her marriage? What would happen to our friendship if we had sex? She was definitely a hottie in physical appearance, and smart too. I didn’t know what happened between Bill and her, but as far as I was concerned, he was losing a treasure.
When I arrived home, I quickly showered and put on panties, a girdle, nylons, bra, a long sleeved turtle-neck blouse, a half slip, an above the knee skirt, and 4-inch baby doll heels. I didn’t hear Jerri’s car drive up when she arrived.
“Wow!” she exclaimed when she came straight in without knocking. “You went all out!”
All I could do was stare at her. She was dressed in a short skirt, button down blouse, nylons and heels, and looked absolutely fabulous. She unbuttoned her blouse and let it fall to the floor. I stooped down to pick it up and she whispered into my ear: “Please go down on me.”
“Right here?” I asked. “I thought we were going to think about it.”
“I have. Please?” she pleaded as she hiked up her skirt revealing very wet panties under the garters on her girdle.
It was all out the window now. I got down on my knees, unfastened the garters and pulled down her panties. They fell to her ankles and she stepped out of them. Licking all around her shaved pussy, I reveled in her scent. She dug her fingers into my blouse and gasped as I eventually made my way inside her with my tongue, flicking her engorged clit. She slipped out of her heels to keep from falling, but was beginning to stagger anyway as I continued.
“Mmmm…” Jerri moaned, becoming wetter and wetter as I determinedly licked all I could. “Please don’t stop. It feels so good!” she said haltingly trying to catch her breath, and with that collapsed onto the floor.
She pulled her skirt off letting it fall to the floor when I helped her up. I led her to the bedroom and had her sit on the edge of the bed while I unfastened her bra. She laid back on the bed massaging her breasts and moaning while I resumed my oral enjoyment of her womanhood with her legs dangling over the edge of the bed. Her breathing became more ragged and as I would briefly touch her clit with my tongue, she would sharply draw another breath. Soon her hands were on the back of my head as if she were trying to pull me inside her. I took her clit into my mouth and sucked, causing her to cum rather violently and squirt into my mouth. I had heard of women squirting before, but never experienced it. This was great! I drank all of her juices I could, and she became almost catatonic for a few moments. I gently held her head until she started to recover.
“Oooh! I’ve never cum so hard in my life!” she exclaimed.
She noticed I was becoming quite uncomfortable. I was squirming since my cock was straining against the fabric of the panties I was wearing and pre-cum was making them sticky.
“Let me help you,” Jerri commanded. “Stand up with your back to me so I can unzip your skirt.”
I did as instructed and she let the skirt fall to the floor. I stepped out of it, the half-slip, and the heels and turned back to face her.
“I see you like to wear girdles too,” she cooed, unfastening the garters holding up the back seamed stockings I was wearing. ”Arms up, so I can take off your blouse.”
She took off my blouse then pulled down my panties, finally releasing my aching cock. The tops of the nylons were now down to my knees since there were no garters holding them up anymore. I must have really looked a mess. She pulled them down as well, kissed the tip of my cock saying “I have to have this inside me,” and playfully pushed me backward onto the bed.
As I lay there with my shaft standing at attention, she briefly licked it all over just enough to make it all wet with her saliva then swiftly mounted me and began riding me like a woman possessed. I reached up and took her 34A’s in each hand, kneading hem back and forth. She was fingering herself as she rode me, and soon climaxed again. The feel of her contractions caused me to cum as well. She collapsed on top of me and we lay there for a while slowly stroking each other’s bodies, basking in the afterglow of feelings while I went limp inside her. Eventually she stood up and I watched her remove the girdle she was still wearing. Like mine, it had a side zipper over hooks and eyes.
“You are so sexy Jerri,” I commented as I watched her, “and you taste good too!”
“Aww, thank you sweetie. I’ve never squirted like that before. It was great!”
“Yes it was, but we made kind of a mess here out of our clothes, ourselves, and the bed.”
We stripped the bed and remade it with clean linen, then took a long leisurely shower together exploring each other’s bodies. After we finished, I gave Jerri one of my nightgowns to wear while our clothes were going through the wash. It was a little big for her and we laughed about her having to hold it up so it didn’t drag on the floor causing her to trip.
“I wish we had not waited so long to do this,” Jerri commented “but I love that you did wait. It means a lot that you feel such a high regard for me. I hope this isn’t a one time thing…”
“Oh it isn’t,” I assured her. “I could become addicted to this very quickly. Just promise me that you will not speak to Bill about it and that it will not happen again until your divorce is final. I am not worried about him, it will just be better that way.”
Jerri readily agreed. We spent the rest of the day just hanging out and talking as friends. The bonding we had shared over the years had become even stronger and by the time she left for home, I just knew I was the luckiest man alive.
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<a href="https://www.lushstories.com/stories/crossdressing/an-old-friend.aspx">An Old Friend</a>