Straight Male / 27
I have been a crossdresser since I was 18. My senior year in high school one of my friends hosted an Halloween party and I decided to go as a girl. I talked to my older sister about it, and she told me I would make a cute girl, and offered to help if I wanted to actually try to pass as a girl. She took me shopping and helped me get fitted for bra's, stockings, heels, a blonde wig, and dresses. She even let me use a pair of breast forms that were her's from back in the day when she "needed a little help". She helped me shave my entire body and taught me how to walk in heels. By Halloween I was pretty comfortable being a girl--she even coached me on getting my voice to sound more female.
Halloween night she helped me apply my makeup and get dressed. My sister finished it all off with blood red lipstick with matching fake nails and polish. She told me guys cannot resist lips with red lipstick and painted nails. The blood red was her favorite shade. I have to admit, even the first time out, I was very passable as a girl. She even got a couple of her friends to go with me to the party so I wouldn't show up and look conspicuous.
After about an half hour at the party, my sister called her friends on the phone and told them she was there to pick them up (We agreed they would stay for a half hour to get me in "unnoticed"). So there I was, solo and after a couple drinks I was feeling fairly comfortable. One of the guys from our basketball team came over and started talking to me. In a few minutes he started hitting on me and I really found myself kind of flattered that he wanted to have sex with me. It totally freaked me out, because I'm sure he'd have pounded my face in if he found out I was really a guy.
I told him that I couldn't have sex with him, but he kept on flirting. One thing led to another and I found myself agreeing to suck him off. We went into one of the bedrooms and I mechanically dropped to my knees. He unbuttoned his pants and pushed them and his boxers down. I didn't have to get him hard, he was already raring to go. He pushed his cock in my face and I opened my mouth. I just slid right in. I no sooner than closed my lips around his shaft and he was blowing his load into my mouth. Since I wasn't very good at fixing my makeup, I just swallowed it down as best I could. I managed to get it down and not get his cum all over my face.
After he started getting soft, he went to the door and opened it. Another guy came in and took his place in front of me. That continued 4 more times. I sucked 6 guys off before I was done. After the 6th one I got out of there. I was starting to think that they were going to gag up on me and try to have sex, and there was no way I wanted to be found out. I quickly made it out to my car and took off.
When I got back to my sister's place she wanted all the details. I told her the party was great and thanked her for the help. She wanted to know if I was convincing. I told her nobody had a clue who I was or that I was really a guy. I never told her about sucking off the 6 guys. I never told anyone about that until a couple days ago.
A few weeks ago I decided I wanted to ask my gf to move in with me, so I told her about my crossdressing. She's OK with it, and my crossdressing inspired a whole spectrum of topics we discussed about sexuality and fantasies over the last several days. She confided that she has always wanted to have a 3some with 2 guys and to watch the 2 guys be sexually active with each other before joining in, that's when I confided that I had given those guys bj's at the Halloween party.
She's good with my crossdressing and she even wants to go out with me dressed, but now she's hinting that she'd really enjoy a 3some. She has even offered to do a FMF if I will do the MFM for her. Honestly, sucking those guys off didn't freak me out. I have since fantasized about doing it again or even being ganged by them. This may sound funny, but I don't have any homosexual fantasies, other than an occasional dream about that Halloween party, I just like to wear women's clothing. It really feels good and it gives me a turn on, not in a sexual way, to pass myself off as a girl.
I know I'd enjoy a FMF and sucking those guys off when I was 18 was not a bad experience for me, it was just something that happened. So I guess I have to decided--be the sissy in a MFM and get my gf to do a FMF for me or tell her no.
Halloween night she helped me apply my makeup and get dressed. My sister finished it all off with blood red lipstick with matching fake nails and polish. She told me guys cannot resist lips with red lipstick and painted nails. The blood red was her favorite shade. I have to admit, even the first time out, I was very passable as a girl. She even got a couple of her friends to go with me to the party so I wouldn't show up and look conspicuous.
After about an half hour at the party, my sister called her friends on the phone and told them she was there to pick them up (We agreed they would stay for a half hour to get me in "unnoticed"). So there I was, solo and after a couple drinks I was feeling fairly comfortable. One of the guys from our basketball team came over and started talking to me. In a few minutes he started hitting on me and I really found myself kind of flattered that he wanted to have sex with me. It totally freaked me out, because I'm sure he'd have pounded my face in if he found out I was really a guy.
I told him that I couldn't have sex with him, but he kept on flirting. One thing led to another and I found myself agreeing to suck him off. We went into one of the bedrooms and I mechanically dropped to my knees. He unbuttoned his pants and pushed them and his boxers down. I didn't have to get him hard, he was already raring to go. He pushed his cock in my face and I opened my mouth. I just slid right in. I no sooner than closed my lips around his shaft and he was blowing his load into my mouth. Since I wasn't very good at fixing my makeup, I just swallowed it down as best I could. I managed to get it down and not get his cum all over my face.
After he started getting soft, he went to the door and opened it. Another guy came in and took his place in front of me. That continued 4 more times. I sucked 6 guys off before I was done. After the 6th one I got out of there. I was starting to think that they were going to gag up on me and try to have sex, and there was no way I wanted to be found out. I quickly made it out to my car and took off.
When I got back to my sister's place she wanted all the details. I told her the party was great and thanked her for the help. She wanted to know if I was convincing. I told her nobody had a clue who I was or that I was really a guy. I never told her about sucking off the 6 guys. I never told anyone about that until a couple days ago.
A few weeks ago I decided I wanted to ask my gf to move in with me, so I told her about my crossdressing. She's OK with it, and my crossdressing inspired a whole spectrum of topics we discussed about sexuality and fantasies over the last several days. She confided that she has always wanted to have a 3some with 2 guys and to watch the 2 guys be sexually active with each other before joining in, that's when I confided that I had given those guys bj's at the Halloween party.
She's good with my crossdressing and she even wants to go out with me dressed, but now she's hinting that she'd really enjoy a 3some. She has even offered to do a FMF if I will do the MFM for her. Honestly, sucking those guys off didn't freak me out. I have since fantasized about doing it again or even being ganged by them. This may sound funny, but I don't have any homosexual fantasies, other than an occasional dream about that Halloween party, I just like to wear women's clothing. It really feels good and it gives me a turn on, not in a sexual way, to pass myself off as a girl.
I know I'd enjoy a FMF and sucking those guys off when I was 18 was not a bad experience for me, it was just something that happened. So I guess I have to decided--be the sissy in a MFM and get my gf to do a FMF for me or tell her no.
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