Erika's Story Ch. 02

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Erika brings GF deeper into her crossdressing.
1.9k words
4.66
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Part 2 of the 6 part series

Updated 06/09/2023
Created 01/03/2020
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Quantarx
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This is chapter 2 of Erika's Story my first story series, If you have not read the first part it might be a good idea to go back and check that one out first. Also I would love feedback and constructive criticism so I can get better. Finally, please rate it at the end so I can see how well it is being received. Enjoy!

***

Three months had passed since the first time I had worn my girlfriend Mary's panties during sex and since then it had become a semi regular thing. I didn't want to freak her out by making it an every time thing, but the nights that the sex included me in panties it certainly felt like things were a lot steamier for both Mary and I. I would have had to be blind to not notice how much Mary enjoyed this kinky new aspect to our sex life, the response was better than I could have hoped for. It is most crossdressers worst fear that they are going to get caught or found out, and that their girlfriend or wife is going to freak out or make them feel like a freak or something. To find a girl that was receptive to me in a pair of silky panties was a really special feeling.

Since I had been crossdressing in secret for years, like most crossdressers I had a bag full of various women's clothing I had picked up over time hidden away in a duffle bag under some stuff in the closet. Erika, as I like to call myself when I'm in girl mode, had a couple outfits to choose from and a little makeup, and a wig to make the look come to life. The one thing Erika had plenty of was panties. Before I had Mary in my life I was wearing them on a pretty regular basis under my normal clothing. If you have never worn panties as a man, I implore you to give it a shot sometime. The fabric of women's underwear is so much thinner then men's, and the stretch and silky feeling is far more comfortable to actually wear. Buy a few pair and give it a shot is all I'm saying.

I had decided it was time to literally get my ass back in panties on a regular basis. Mary and I were planning on hanging out tonight at her place and ordering a pizza, so I decided today was the day to take the next step of my plan. I looked over my collection of undies and decided on a purple satin pair that was a sheer mesh in the back that were almost a matching color to this little negligee I especially enjoyed seeing Mary in. Sliding them up my legs and into place, taking care to tuck my cock away inside the smooth material. It was nice to have my own panties on again, don't get me wrong it was kind of hot to wear Mary's panties during sex, but I was tired of the men's boxer briefs and boxers I had been wearing most days. With that, I pulled my jeans up around my waist and walked out the door on my way to Mary's place for the evening.

When I got the Mary's apartment, she greeted me at the door wearing a cute little blue dress that flared out at the bottom hemline with a little lacey detail. Mary apparently had been missing me since it had been a couple days since we had been able to spend any time together. She threw her arms around me and gave me a hug and planted a kiss on my neck, lingering for quite a while.

"I missed you babe." She whispered into my ear in a sexy voice that told me what she actually wanted.

"Well, lets take this show to the bedroom and I can get you out of that little dress."

She grabbed me by the jacket and nearly dragged me off to the bedroom. Mary was such a horny little thing, I'm such a lucky guy to have a girlfriend that loved to get fucked. Some women have sex, and some women "fuck", I got lucky when I got my hands on Mary and found out that she was a dirty little bitch that really enjoyed a good fuck.

Arriving at the bed, she spun me around and pushed me down onto the bed. Turning around, she bent over slightly at the waist and slowly slid her hands up her legs lifting the bottom of dress as she went, exposing her cute little ass covered in a black lacy material the framed her ass in the most perfect way. Hooking her thumbs into the waistband of the lacy panties, she starting inching them down her legs ever so slowly. Upon reaching her ankles, she paused slightly allowing me to have a good look at her pussy and ass before stepping out of them and turning around to dangle them in front of me.

"Put them on baby, I want you wearing them while I suck your cock."

Reaching out to feel the panties being offered up to me, I noticed they were still warm from the heat of her body. The twitch in my pants at this realization reminded me that I was already wearing a pair of panties.

"Well hun I'd love that, but you see there is a bit of a problem with that."

I could see the expression on her face turn to disappointment at the thought of me declining her gift. With a bit of relief at seeing her disappointment, I felt a bit of courage grow inside me and stood up from the bed and undid my jeans, letting them fall to the floor.

"Well... I figured it was about time I got my own panties to wear and stopped stretching out all of your panties before we had to go shopping buy you all new undies."

Mary looked at me with a bit of a raised eyebrow before looking relieved and giving me one of her award winning smiles that melted away the tension in the room.

"Honestly baby I had been wanting to talk to you about that, I already had to throw out three pairs and was trying to figure out how I should tell my boyfriend that I wanted him to get his own panties."

"You wanted me to have my own panties to wear?"

"Of course silly... I love seeing you in panties, cant you tell how excited I get when you wear them?"

"I have noticed that you cant keep your hands off me when I'm wearing your panties, but I was afraid that was just a sex thing that you would thing was creepy if I wore them outside the bedroom."

"Look, a few months ago maybe I would have laughed or thought you were a weirdo or pervert." Mary chuckled for a second. "Maybe you are a pervert, but If you're a pervert for wearing them, then I must be a pervert for liking my man to wear women's clothes."

"Women's clothes, not just your underwear?"

"look baby.. before we started our relationship I'm not sure I'd ever put much thought into crossdressers to be honest, but that first night I painted your nails and you wore my panties while you fucked me, something changed." Mary looked down a little bit looking a bit sheepish. "Do you know how many times I've masturbated since that day, thinking about you in panties, bra's, lingerie, etc... hell a few times I came so hard I had to change the sheets"

Thinking back to when I was afraid to open myself up to her and let her in on my dirty little secret, I could have never hoped that she would be so accepting and even encouraging.

"Well now that you have your own panties to wear, I guess you don't need these." She said with a smile tossing her panties onto the floor by the laundry basket. "So don't just stand there like a goof, take the rest of your clothes off and let me get a look at your new panties."

I stepped out of my jeans that were still around my ankles and pulled my t-shirt over my head. Standing in front of Mary wearing nothing but my frilly purple panties I could tell she approved of my selection. Mary cupped my package through the material making my erection twitch a little. Figuring that she might appreciate the see through mesh panel in a back I turned around slowly and bent over the bed a bit. Mary's hand never left my body as I turned around, I could feel her finger tips tracing the waistband of my panties as I turned, her hand now rested lovingly on my panty covered ass.

"I like your new undies baby, the mesh in the back gives me a nice view if that cute little ass, and the color reminds me is that baby doll nightie I have."

"I thought the same thing when I picked them out, I've always liked that nightie on you."

With that she took her hands off me and walked over to her closet and started rustling around. I moment later she returned with the matching purple nightie and another white one in hand. She handed me the purple one while she started to put on the white one. Following her example, I pulled the frilly purple lingerie over my head and let it fall over my chest into place.

Mary planted a big kiss on my lips and gave me a push backward onto the bed. Crawling on top of me, She continued to make out with me pushing her tongue into my mouth feeling around for my own. Our bodies rubbing together in the frilly material of the lingerie was giving me a massive erection that was grinding into Mary's leg.

Noticing the erection in my panties Mary scooted down the bed until her face was level with my cock. With one hand she pulled down on my panties and as my cock popped out of their silky prison , her mouth came down over my dick and swallowed it down in one gulp. Slowly her head began to bob up and down, her lips milking my shaft with every motion. I was so turned on from the afternoons events, I wasn't going to last long at this rate.

"Baby , I'm going to cum if you don't slow up!"

Mary's pace picked up and I was left helpless. My cock spasmed in her mouth and she swallowed me whole until her lips were wrapped around the base of the shaft.

Spasm after spasm shot my hot cum down her throat as she moaned unto my dick.

Slowly the orgasm ran its course and my tool began to go limp and she let it slide out of her mouth sucking and licking as it went so she could get every drop of cum off it.

Mary's looked up at me wearing her lingerie and smiled. slowly she crawled up beside me in bed and started to snuggle me. I looked her in the eyes and gave her a big kiss, I could still taste my cum in her mouth but at this moment I didn't care in the slightest, honestly it was a bit of a turn on tasting my cum on her lips.

We laid there with our bodies wrapped in silky lingerie and held each other not saying a word because nothing needed to be said. We both knew this was just the beginning of something we were going to experience together, and were excited to see what was next.

Thank you so much for reading and please leave a comment or rate the story so I will know how to get better for the future!

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16 Comments
richgo50richgo50over 1 year ago

Thoroughly enjoy reading your stories. I do wish Erika would have sniffed Mary's panties when she gave them to him.

b8masterb8masterabout 2 years ago

Wonderful story, had me hard and wet in my silky panties, a great woman you have there.

davasubdavasubabout 2 years ago

The story is wonderful

AnonymousAnonymousalmost 3 years ago

Wearing panties and thigh high stockings feels so good to make love in

SissyArleneSissyArlenealmost 4 years ago
Great writing.

I love the mutual exploration of Erica's awakening.

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