I was 23 and in the US military back in the late 90s. I was a panty wearer since my late teens and continued despite being in the military. One night, I put panties on and left base. I was particularly horny and decided to try a phone chat line. I talked to some local people but nothing much happened. I was about to give up when a random guy started chatting. He asked about my interests and what I was open to. I told him I was open to most things. I admitted I was in panties and horny. He asked if I had ever been with a man before and I said no. He asked if I was interested? I told him I had been curious a time or two.

He asked where I was and I told him. He said he was actually very close. He suggested that we meet at a bar and just have a drink. I agreed. Turns out it was a gay bar. So we talked for a while and drank some. I excused myself to the bathroom. When I came back, he told me he liked the pink panties I was in. He said he noticed them above my pants when I walked off. I was so embarrassed. He said it was ok, he liked it.

It was getting late, and he asked if I was ok with going back to his place to continue drinking. I said sure. We got there and had a drink, and he asked how i liked wearing panties. I told him i was really into it. He asked to see them, and since I was drinking, i agreed to show him.

As I was pulling my pants down, he got in front of me. He started rubbing my ass in them, then worked his hands around to the front. He rubbed and stroked me. Then he kissed me through the satin. It felt so good. He asked if I wanted to try. So we sat on the couch. He guided my head down. He was still semi soft. He wrapped his hand around himself and pressed it to my lips. I kissed and licked him. Finally he pushed it into my mouth.

The warmth against my tongue and him sliding in and out felt so right. I could feel him getting harder with each thrust. He said he needed to cum, so he pushed and filled my mouth. It was so much that it leaked out and down my chin. He looked down and said he wasn't done yet and for me to keep sucking since I was doing it so well. He went limp, but after a few minutes he started getting hard again. He told me I was a good girl. He told me he wanted to have sex and asked if I would. I said yes but that I'd never done it before.

He got up and said he would be right back. He came back with a plastic bin. He showed me it had all kinds of women's clothes. He said they belonged to his wife who passed away. He asked if I would dress up for him since I was already in panties. I agreed. I picked out stockings, a garter, a bra and a short night gown. I went to the bedroom to change.

I came out to him holding a little black dress. He put it on me over the lingerie. He spun me around then walked up behind me. He pulled me close and I could feel him throbbing between us. He wrapped his arms around me and kissed my neck. He grabbed his cock and slid it down my ass and between my legs. He grinded against me. He turned me and kissed me again and pushed me on the bed.

He got between my legs and pressed the tip against my hole. He grabbed my legs and put them over his shoulders. He grabbed a condom and put it on. I could feel him stroking himself as he pushed the tip in. He leaned down to kiss me again and as his lips touched mine, he pushed himself completely in me. No warning, just the tip and then all 7.5 inches buried in me. He held it there and kissed me before he started slow, deep thrusts.

It was hurting at first, but it turned to pleasure after a few minutes. He was long, but kind of thin, so the pain wasn't too bad. He fucked me for a while. I wrapped my legs around him and pulled him close and deep. After about 30 minutes he said he was ready to cum. I pulled him deep and he pushed and held it there as he started to cum. I felt him get very hard. Then I could feel him throbbing inside me as he started to cum. He leaned down and kissed me again. When he did, he pushed a little deeper. I was in heaven, it felt so good.

He asked if I needed to leave, and I said no. So I ended up spending the night. He got me a different set of lingerie to wear and I changed. We spent the night teasing and cuddling. Finally he fell asleep and then so did I. I woke up to his hard cock poking me. I rolled over and grabbed him and sucked him again. This time it took a while to cum, but I didn't mind. He finally came in my mouth again and I swallowed every drop. We fooled around quite often for another year or so until the military moved me away.