Being Robin

My Name is Bob. Today I am very comfortably bisexual. I have had relationships with both men and women. Yes, I am a bit of a metrosexual, but most people don't tag me as gay, just well put together. I am handsome, but not chiseled. Thin, but not too thin. At five foot six, I'm on the shorter side. Women like me both as a friend and as a sex partner. So do a lot of men.

What I am going to talk about took place twenty years ago when I was eighteen. Back then I knew a lot less about myself. I was a virgin. I sort of assumed I was gay, but I also looked longingly at girls. A lot of people also assumed I was gay including girls who I became friends with. A few of these girls were very attractive and because they assumed I was gay would frequently change clothes around me. One close friend, Lisa, would have no problem getting completely nude in my presence forcing me to figure out how to hide a raging boner.

So anyway, there were unresolved sexual identity issues.

One day in early fall I was over Lisa's place just hanging out and I saw her staring at me.

"What?!" I said.

"You have a very pretty face!" I laughed and also blushed a little. The truth is that as a boy I did have a rather feminine face. Delicate features, somewhat full lips. I suppose that the fact I had shoulder length chestnut hair at that point in my life may have added to the effect.

"Thank you, I guess."

"No really! I think you are prettier than half the girls I know." She eyed me speculatively. "Have you ever tried wearing makeup?"

I was shocked "God no! Why would I?"

"I don't know, just out of curiosity maybe. I'd like to try making you up."

"No! That would be weird!"

"Come on, It'll be fun!"

We went back and forth for a little bit and I finally relented. Just a little harmless fun and then I would wash it off. No biggie."

I had pretty clear skin for a teen so she didn't use a lot of foundation. She accented my cheekbones, penciled around my eyes, just a hint of dark on the lids. She gave me a pretty pink gloss on my lips. It was really quite minimal. She finished off with a pair of false eyelashes. She did my hair just a bit differently combing it low across my forehead. She turned me toward the mirror and there was the face of a girl I wanted to get close to! I was hot! "Woah!" I breathed.

"You are gorgeous!" Said Lisa. "Let's try something else. Take off your clothes!"

"What?"

"Strip. We are going to dress you up!"

She put one of her bras on me. She was a 'b' cup and stuffed it with a couple of pairs of her panties and gave me a pair of white thigh high stockings and a pair of slightly high heels. It turned out that I had pretty good legs! Finally she put a short plaid skirt and a white blouse on me.

She stepped back and looked me over. "If you were a real girl, I would totally hate you!"

A stranger looked back at me from the mirror, a pretty, no strike that, a damned sexy stranger! Lisa started laughing.

"What's so funny?"

She was pointing at the tent in the front of my skirt. "You have a boner! Do you suddenly like girls?"

I pointed at my reflection. "I like that girl! "

Lisa took out a Polaroid camera and snapped a few photos for which I obligingly vamped in some and just tried to look pretty in others. We just hung out for the rest of the day at her place with me dressed as a girl, with me having sort of become a girl. The fact is I liked it a lot. She also let me get closer than we had ever been before. We kissed and cuddled and were holding hands most of the day.

It one point I boldly reached out and cupped one of her breasts. "I wish mine were this nice, that you could touch them and it would feel like a tit and not a wad of cloth."

"Hmmm. They make silicone fake ones for drag queens. You could get a pair of those!"

I suddenly wanted them badly!

When I had to go home I put on my regular clothes and washed my face, but I had definitely caught the bug for being a girl. Over the next week I talked with Lisa about maybe being a girl for Halloween! We wouldn't tell people who I actually was and see if anyone thought it was me. During those next few weeks we would play dress up whenever I came over and her parents weren't around. I ordered some outfits of my own and a pair of smallish silicone titties.

Lisa waxed almost my entire body and I started using moisturizer regularly. Thos fake breasts were far better than I had expected them to be. They actually looked and felt very natural. The back side of them had the edge of the plastic thin to almost nothing at the edges. We attached them with a cosmetic glue and applied just a bit of makeup around the edge. The effect was stunning! Even topless, I just looked like I had natural breasts. Lisa and I laughed and felt each other up and, yes, you better believe I got a hard on!

She pointed at my dick. "That", she said, "Could be a problem." I discovered that I could just push my balls up inside me, pull my dick back between my legs and then just hold everything in place with an Ace bandage over a pair of panties. It worked pretty well so long as I didn't have to pee.

The final effect in clothes was pretty near perfect. Luckily I have never had a prominent Adams apple and at that stage of my life I still had a pretty sexually ambiguous voice. If I talked like a girl, I sounded like a girl. We decided that as a girl I couldn't go by "Bobby" so my girl name became Robin.

I was now eager to try it out even before Halloween. We went out to the mall. I dressed in a pair of cutoff shorts, a t-shirt and sandals. Nothing over the top, but the t-shirt was pretty tight and my tits were adhered strongly enough that I decided to try going braless. Well we both got a lot of appreciative glances from boys our own age and also from older men. It was the older men whose eyes I noticed the most. Honestly, if I had a pussy, it would have been wet just from those looks. I mentioned it to Lisa.

"Yeah. There are a lot of creepy old guys out there!"

"Creepy. I think I want all of them to fuck me!"

Lisa giggled. "Slut!"

"I could live with being a slut!" We both laughed.

We window shopped for an hour and then returned to her place.

The first thing I did was strip off my clothes and free my dick from bondage. She had gotten naked too to put on a swimsuit so we could go hang out by the pool. There I was wearing nothing but a pair of fake breasts with a straining erection.

She looked at me and my eager penis. "Bobby, do you like girls?"

"I like you. I like you a lot." She nodded her head and I could see that she was trying to wrap her mind around new information. She walked over and gave me a hug, full naked body skin to skin contact. Like I said, I was a virgin. I had never been close to a girl in that way before. She kissed me on the lips and reached down and wrapped her hand around my cock and started gently stroking. I ejaculated all over her belly after only a few strokes. It was up until that time the best orgasm I had ever had.

She was ok with me touching her all over her body. I excitedly licked my own jizz off of her skin and attempted to eat her pussy, but I was bad at it. She, like me was a virgin and didn't want to have intercourse. It would be another two years before I actually got laid by a woman.

Later we went for a swim. I had removed my tits and cleaned off my makeup and was wearing trunks. A week or so later we figured out a less bulky way to tuck my package so I could wear a bikini.

Halloween was approaching and I had to work on my costume. I had decided almost from the beginning that I wanted it to be as sexy and provocative as I could get away with. I came up with an elf girl outfit that was mainly pointed extensions on my ears and a little pointy hat. The rest was a tight white tube top that the shaded nipples of my fake tits could be clearly seen through a very short green skirt that ended actually above my stocking tops and a pair if high heels that gave extra oomph to my butt and legs! I was going to get quite a bit of attention!

Lisa had a Catwoman outfit that was itself pretty eye catching.

The Party was at the YMCA on the Friday night before Halloween. Lisa had a date and I was just tagging along. Chuck, Lisa's date seemed pretty happy to be escorting two pretty girls!

Lisa introduced me to people who I mostly already knew as her cousin Robin. A few people asked about me, the real, male me that is. Lisa told them I was out of town visiting relatives. No one obviously saw me underneath Robin.

A lot of males were taking good long looks at me. It was weird and wonderful to receive that amount and kind of attention. As a guy people didn't really look twice at me. I wasn't an outcast or anything, I had lots of friends, but this being devoured by men's eyes was a whole new thing.

One of the people that Lisa introduced me to was someone I hadn't met, a city councilman named Jeffrey Wardman. He was about forty with slightly graying brown hair worn in a classic crew cut. He was wearing sort of a Fred Flintstone cave man outfit. He was also drop dead gorgeous. I gave him my very best smile and made some pointless chatted about how interesting it must be to be on the city council. He asked how old I was, I think because Lisa, who he knew to be eighteen introduced us. I told him I was twenty two.

"Over twenty one! Well then we should get you something a bit more adult than that fruit punch!"

I smiled coyly. "Whatever you are having mister Wardman."

"Call me Jeff. I'm having scotch and soda. I'll be right back. Don't go away. I want to learn every little thing about you!" Ok. I had only had very occasional alcoholic drinks before, an occasional beer with friends at parties. Never any hard liquor .

Jeff was back quickly with our drinks. We clinked glasses and I took a sip of my scotch. It was strange, but tolerable. To this day I don't really care much for brown liquors. I mostly like vodka mixed with various things.

Jeff was very attentive. I tried to get him to talk about himself rather than attempt to give myself a detailed back story that I would probably forget. It wasn't difficult. Men love to talk about themselves. Jeff was recently divorced, no children, ran a Toyota dealership, was elected to the council just six months ago, hated golf, but loved basketball and in general liked to keep in shape. He didn't seem all that deep, but he was awfully nice and utterly sexy. People sometimes talk about some men having "smoldering eyes", well he had them and was using them to check me out thoroughly. I was showing about as much of my tits as I could get away with and not have them be spotted as fake or get me arrested. Thankfully the lighting in the room really worked to my advantage. Looking at pictures taken that night I just looked like a cute, very fuckable girl with cute little boobs. I wanted to fuck me!

I was getting the distinct impression that Jeff wanted to as well. The feeling was mutual, but it would never work. Before I knew it I had finished my drink. "Hey, what do you say I get us a couple more drinks and go to one of the offices where it's quiet and we can really talk." I smiled and nodded. I was wondering if I could at least get away with kissing him.

The office of the lodge treasurer had a harsh overhead fluorescent light. I switched it off as soon as Jeff switched it on and turned on the desk lamp instead which gave the room a lower lever, more intimate ambience. "You're right. That's better." He said.

We sat on the office couch to chat and drink. I inched closer to him and started touching him on the arm to underscore words in our conversation. I have to tell you, I do not remember one word of what we talked about. That conversation was just friendly noise floating above our mutual horniness.

I finally touched his face and then kissed his lips. God, it was fantastic! As I said I had considered myself gay at that point, but I had only experimentally kissed a few guys my own age. Me and friends, mostly more or less hetero ones had played with each other's cocks a bit, but really I didn't have that much experience with men, let alone a mature and very hot man.

It was a great kiss followed by several more and then his hands were on my chest. I could feel that he was squeezing my fake tits. He didn't seem to notice anything strange about the way they felt, but if he pulled them off of me he would certainly notice that! I had to think of something quick.

I pulled back a little bit from him and moved my hands down his body. One of my hands came to rest on his package. I could feel his dick was getting hard. Mine was too which was another problem. So far it hadn't insisted on breaking free of its bonds, but that was only a matter of time. I slid both of my hands underneath the cave man frock that he was wearing boxer shorts underneath. His cock was rock hard. He was average sized, but it seemed large to me at the time. I looked him in the eyes and asked, "Can I take him out?"

"Please do!" he said in a harsh whisper. I lifted up the costume and pulled down his underwear. I gripped his cock in my hand and put my face close enough that he could feel my breath on it. As I had hoped, he had completely forgotten about my tits.

I kissed the head of his cock and my tongue flicked out to taste his precum. It tasted so good it made me a little dizzy! I kissed and licked it a bit more and then took the head into my mouth. "Robin!" he moaned.

I had never sucked a cock before, but I was clear on the basics. I wasn't going to try to get fancy. I wanted to satisfy him, to taste this beautiful man's cum and then get the hell out of there before I blew my cover! I could now actually feel one of my tits working its way loose and my insistent hardon slowly undoing the bandage.

I stroked his cock with my hands while sucking on the tip bobbing my head up and down. My God, I mean my God, it was utterly like heaven to suck this man off. Then and there, there was no doubt that I was going to be a cock lover for life!

His hips bucked and he grunted and released a huge mouthful of semen which I swallowed and then another. I released his penis from my mouth even as a few last little pumps of jism oozed out and ran down his shaft. I leaned over and greedily licked it all up.

I sat up. No doubt I looked a mess with my makeup all smeared and drops of cum on my face. Jeff breathlessly exclaimed, "My god, Robin! You are something else!"

And I said, "Jeff, you are a beautiful man!" I waited a beat. "I need to go now!" and I got up and scrambled out of the room.

I went to the ladies room and fixed my face as much as I could, tried to stick my right tit back on as well as I could although the tube top was doing most of the work holding it in place. My cock was staying put so far. I ran out and found Lisa and said that we needed to get out of there. She and Chuck drove me back to her place. I think that Chuck might have thought I had been raped based on my dishevelment. I assured him that I had not been violated, that I had just made a poor life choice.

That night, Lisa and I slept in the same bed, naked together. We spooned for a while with my erect cock nestled in her butt crack and my hands holding her perfect titties while I told her exactly what had happened that night while I slowly stroked my dick against her. She giggled when I came and said, "You are such a slut, Bobby!"

I only played the role of Robin a few more times. We figured out how I could wear a bikini (but not actually swim in one) and went on one double date that winter. My date was a college boy who played basketball. He also had a delicious cock. God, Robin really was a slut!