I used to have a girlfriend, Sandy, who used to dress me in femme and we would play for hours.
I think this all started when I was sixteen and started wearing my sister's bras, slips and panties. I loved it back then.
I was insecure about telling Sandy about all this, so one afternoon while we were playing, I hinted that I loved the feel of her panties against my balls. She let me try on her panties and I immediately got hard, this turned her on. One thing led to another and she would let me dress up every time we met.
We were both turned on by this and eventually she started to take charge. She started asking me if I had fantasies about being with a guy. At first I denied it, but she persisted. Eventually she introduced me to a seven-inch strap-on.
At first she would have me fuck her with it and have me lick it clean. Then she would tell me she wanted to watch me suck it and I eagerly submitted. Sandy taught me how to suck and deep throat, I loved it. We would roll reverse and she would wear jeans with the strap-on tucked inside. She would seduce me and I would end up between her legs stroking and sucking as she pushed my head down deep on "Her" cock. After lots of practice/play she told me she wanted to watch me really suck on a guy and how much she would be turned on by it.
Sandy told me she had a girlfriend and her guy who both wanted to party with us. When the first meeting day came, she had me dress in a white blouse with a black skirt, over a lavender bra and panties and black thigh high stockings. She prepared my make-up and told me how sexy I looked, and that I was there for the pleasure of her guests.
When they arrived, I nervously greeted Kris and John at the door and invited them to come in and make themselves comfortable. I asked them what they would like to drink and proceeded to the bar to mix drinks for all. As I walked by John he stopped me and slide his hand slowly up my thigh which sent shivers of anticipation through my body. After drinks and a little small talk, things started to heat up when Kris started kissing John as her hand slide to his crotch.
Sandy whispered in my ear that I should slide over and join them. I slid down and knelt in front of John, Kris took my hand and placed it on his bulging cock. With a little encouragement from both girls I unzipped John's jeans and to my surprise, he wasn't wearing shorts. His seven inch cock sprang out and I took him in my hands and slowly stroked his shaft.
He was cut and with little hesitation, I slowly licked the underside of his shaft, which twitched as my tongue slid to his head. I wasted no time and circled his head with my tongue tasting his pre-cum. I could hear him moan and the girls giggling in delight. The girls were deeply interested in watching me play with his cock and I heard Kris whisper to Sandy that she taught me well.
As I took him fully in my mouth, he held the back of my head and forced his cock deeper, and I eagerly started to slide my mouth slowly up and down his hard shaft. As I worked his hard cock, I would slide him deep and hold him in my mouth and slowly slide back to his head. His moaning increased and I started to run my wet mouth up and down his shaft faster. I could feel he was ready to release.
The girls started telling me how hot it was watching and urged me on, which excited me even more, and I wrapped my lips around his cock as he exploded warm spurts of cum in my mouth. Having never tasted cum, other than mine, I was eager to show my Sandy that I could take all he had. I swallowed all he had to give without spilling a drop, much to the girls' delight.
As I knelt between his legs, I suckled and milked his cock until he became soft in my mouth. Sandy knelt beside me and we kissed deeply for several minutes after which she told me what a good little cock sucker I had become.
Kris and John both echoed her sentiments, and John told me it was one of the best he had.
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