Dress Up

We lived in a house together where I rented a room from Tony. We were all hippies and had lots of highs and great, great music all the time when we were not working.

Tony let some guys stay in the living room often when he would meet them out partying and they would need a place to crash for the night and sometimes longer. One time he has these two guys stay and one was so cute, we stared at each when I first saw him. Dark hair and nice muscles, looked good lying on the floor in his blankets in the morning as I walked by for coffee. His friend had a huge penis, it was so big it was... interesting to look at, but I like them much smaller because I like one that is pretty not ugly and I like anal sex so I don't want one too big for that pleasure. You may be wondering how I saw it, it is because Tony had a naturist house rule, anyone can go nude any time they want and he told them so when they came in to stay and gave them a few rules, like always making sure anyone who came to the door was 'cool' or anyone visible in the house had to have something on, etc. Sometimes we would masturbate together in the living room after partying with some awesome music on, but that's another story.

So this friend that I liked, he turns out to be really a nice guy, no pushiness or arrogance and so we get together and make out a few times. I have the master bedroom in the house and to be sure I'm gorgeous, with big tits and southern beauty, so all the boys are always pestering me and I have to be very 'cruel' and aloof to try to keep them away. But this guy Sandy is so cute!

So it's Halloween a few weeks later and I'm trying to think of some great costume for all the awesome parties coming up, we would go dancing at a Castle Ruby club with about 300 people in costumes and Electronic and Rock Dance shows with projectors and laser lights and dance cubes and pedestals, was really awesome we would be partying out in the back patio where you couldn't smell our partying. So I come up with the idea,(I really wanted to tease and test Sandy) some people I heard did cross-dressing, so I told Sandy if he wanted to go with me I wanted him to Cross dress with Daryl! Also another thing Tony came home too when they were nearly ready. It is amazing how a beautiful girl can get guys to do ANYTHING when you show them some pussy and boobs, and they know they are gonna cum with me if they keep me happy and do what I say!!!

So when Tony sees Sandy and Daryl (with the big penis) in the bathroom while I'm putting on their lipstick, he gets all excited and nervous, I know this is gonna be even more fun! Because Sandy and Daryl tell him that he has to shave his legs and dress up too! He baulks at this and said that his sisters and girlfriends tried to get him to do that many times before on Halloween but he is a guy and is not going to do THAT!!! So I get him alone and tell him I WANT HIM TO, If he is a brave man he will be able to what Sandy and Daryl are already for, then Sandy and Daryl come in start teasing him and telling him he is just a closet case and can walk around the house naked but can't be seen at a party cross dressing with them and they already shaved their legs too!!! We totally talk him into it! We find some more stuff like a bra and a open bottomed girdle from the stuff we collected at the thrift stores. We get him to shave too!! They all look so cute after I have put red lipstick on them all! They are all so cool. I've got Sandy and Daryl in catholic school girl outfits with white knee high socks and of course with plaid skirts and bras under their blouses, wigs and everything, then Tony as a Dominatrix sort of in the open bottomed girdle with condoms on the stocking holders!! They were a scream!

So off we went! and after some more partying we were ready for some wild dancing for about four hours. Lots of indescribable scenes of kissing, hugging and fake sex on the dance floor! I find Tony and he tells me about his night and tells me that he is so embarrassed at first, but is now getting used to the bra and people staring at 'him'. He tells me how a girl he was talking to reached up and squeezed his tits and asked deceitfully 'are these real'... haw, haw ... to which he put both hands on each of her tits and asked deceitfully 'are these real'? So he is amazed that she doesn't react but lets him fondle her longer!! He tells me then he tried it out on all the girls he could talk to!! He said 'I must have squeezed about 30 pairs of breasts and it is such a turn on! Girls will let other girls touch them! If your dressed like a girl, they will let you do anything! They even tried to get him to go into the ladies room with them!! He wouldn't go but I think he should have, maybe they would have made him perform for them with his interesting anatomy!!!

So we go home and get back to our cozy living room and I give them all what they are dying for, I do a very sexy strip tease in my black lace bra and panties, then down to my garter belt and stockings, my big tits out, with hard nipples (eraser size) and hanging free, I bend over a let them see my open, wet cunt with pink, pink, pink folds of my inner and outer lips, and slowly move my hands up from my ankles to my cunny, then I notice they can't hold it any more and are stroking their nice cum filled genitals! I love to see their hardness and smooth skin on the heads and the excitement in their eyes!

So then I tell Tony I want him to kiss Andy and have them stand facing each other and then reach up! I hold their heads together. Just one short kiss, but it made my liquid drip down my leg! Then I told Daryl to shoot off. My super sexiest voice made him go wild and shoot pretty quick! Then I (I love telling them what to do!) put a finger inside myself and tasted it, inches away from his face, that made Sandy shoot off! Then I concentrated on Tony and made him act and walk like a girl and talk in a high voice and tell me that loves dressing up! I tell him he has to do what I say, and that he HAS to enjoy it, that I want him to!

That sends him over the edge and he cums on my tits as I'm kneeling right in front of him, teasing him with my sexiest sweet and sultry voice. Then I make them all put their genitals near my face as I lay on the floor so I can touch them as I finger myself, so wet and my clit is so hard and my nipples are too! My mound and black bush look great with the black garter belt.I get closer and closer and finally I fantasize that each penis is squirting on me and I cum so hard! My whole body shudders and I'm screaming and bucking, I'm not stopping either, I'm rubbing my clit and putting fingers inside my pussy and ass too!! I'm getting ready for another big orgasm and getting sopping wet! I'm watching the boys over me in their bras and lipstick and I love it! I cum many more times and we all shower and clean up and go to our own rooms.

The next day we all decide that it was so much fun we are gonna do it again, and for the next two nights we find a party on a mountain, in an old mining town in AZ and then another brewery party! Now I don't have to force Tony, he said he wished he had the nerve to cross dress sooner as squeezing tits is so much fun and they always let him do it! He tells me in the months ahead of other adventures he is having because his girlfriend (I told her!) somehow found out and is making him dress up for her as a maid to do housework, then she does it with him all night, and makes him dress in a evening gown and makes him show her how to please a woman as only a woman can!! I'm so glad I started him into another hot way to keep love and sex interesting and fun! Have fun yourselves, I hope you enjoyed this! please comment if so.