First Fetish Site Meetup

Out of curiosity I joined a fetish site and posted some pics of myself dressed as a girl mostly in high heels and stockings listing myself as a part time hetero-flexible fetishist. I made a few long distance friends and followed some amazingly passable self described Subs, Sissies, Cougars, Sluts and Bottoms. This was a real education for me into a new world of kink since i had only been with one lover for many years. I had always been interested in women's clothes and dressing feminine and after a messy breakup had the freedom to dive in and check things out. I started a routine of logging in once a week and searching for local sissies finding an active sissies, CD and Femme group someone was always posting on. One day I noticed a local girl replying to a CD asking for help in becoming more of a girl and to be more confident. The reply was from a much older gender fluid girl who wanted to help out. When I checked out their profile the words soft, sweet gender fluid girl looking for fun and play really sparked my interest.

The photos had to be a woman's body with nicely shaped B cup breasts and amazing nipples on a soft and supple looking girlish body. I was intrigued and messaged them out of curiosity and soon received a reply! We messaged back and forth about how they used estrogen supplements to grow such girlish breasts and common interests such as women's clothes and shopping. After just a few messages they said their name was Ava and they were going shopping this coming weekend also they would wear a little bra so I could enjoy their breasts. I was very excited and nervous at the same time but thought why not do a little shopping and get to know Ava. We decided on a time early in the day at a thrift shop several miles from my place and half way between us. I had offered to dress as a girl but Ava said they would be comfortable with me dressed as a man. I read from their profile they liked being called a good girl so started referring to them as good girl Ava.

The big day finally arrived and I set out early in the morning to meet Ava at the thrift shop and arrived when they opened. I walked around the store and thought they might be there bought a few things and got nervous since the store was so busy. I left just as they were arriving. I drove away and checked messages on the fetish site and they were very upset I was late and had left. I had to decide then and there if I was going through with meeting Ava and hurried back to the store.

I walked into the store and right over to the dress aisle where Ava was shopping to apologize for being late. Ava is much older than me and had gray hair and was dressed androgynously in jeans and a loose flannel shirt which was unbuttoned enough to show off her bra. I just blurted out nice bra, she smiled and said it's actually a swim suit top.

I had just about given up on Ava ever forgiving me for being late, scared and nervous when she gave me a smile and showed me some cute things she had picked out. We shopped a little more paid for the clothes and walked awkwardly to our cars thinking we would part ways.

Ava asked if I wanted to sit and talk for a bit and I eagerly accepted. We sat in her mini van and casually discussed things as she unbuttoned her top and the bright swimsuit top held the most amazing breasts where i could almost make out her nipples just like in the picture on the fetish site. Just as she was unbuttoning her top a car pulled up in front of us and a man was staring in. She said hold on and we backed out of the stall and drove around the store to the back parking lot and a shady spot. It was nice to be alone and her voice and mannerisms were so feminine she made me feel comfortable in her presence. As she pulled her top aside I was transfixed on her pert girlish nipples and asked politely if I could feel them. She said sure and I gently started tracing them on top of the swimsuit top and they really stood out and slowly reached in for a handful of her left breast. At this point she asked if I wanted to sit in the back seat so we got out in the parking lot and hopped in the rear seat of the mini van. I sat to her left and soon had my tongue licking her nipple and feeling the other one at the same time. She was quick to slide off her jeans and had the cutest light blue panties on with a little pink bow. I traced the outline of her erect member that fit so nicely in her panties and remarked on a little wetness on the tip of her clitty and she said just like a clitty should be wet. I felt her soft supple thighs and continued to lightly stroke her panties as I was able to put her entire left breast in my mouth and she actually moaned with delight.

Ava had a selection of girls clothes in the middle seat so stood up to pick up a pink bra and a micro mini grey skirt. I couldn't resist so started cupping her bottom with both hands and she bent over more and said she likes to be spanked. Her bottom looked amazing in the high cut panties so I started spanking both her cheeks alternately. Good girl Ava's bottom was too appealing so i started fingering her girl pussy though her light cotton panties and she ground against my finger. This all happened so fast and my cock was straining through my jeans although I hadn't brought any condoms so asked if she had any toys. Also in the middle seat among her girlish clothes was a small purse with the most life like dildo and container of lube. She used a small amount of lube first on her girl hole then on the tip of the life like dildo handing it to me and leaning over the middle seat. I slowly inserted it into her bottom and she moaned and ground her amazing ass into it and in no time was fully inserted into her. I was amazed at how the entire length disappeared into her. It had gotten so hot and steamy in the backseat we soon took a break and she pulled on the cutest jean shorts and we chatted more outside the van as shoppers were dropping off donations for the thrift store just a few parking spots away. Driving home I pulled over and thought did that just happen? It did and I started messaging Ava on the fetish site describing how her amazing nipples and breasts felt in my mouth and how cute she looked in her pink bra and grey micro mini skirt.. Later that night Ava replied thanking me for coming back to the store and that she wanted to be both a good and naughty girl with me next time.

hopefully to be continued...