A Trip to Remember Ch. 02

While I am dressed in compromising clothes I am picked up by a sexually aggressive female

We continued walking and I again said that I didn't think this was such a good idea. Judy turned to me and said "Look, you did this to yourself for a sexual charge. Believe me; I have had more sex with more people than you ever thought of having. If you really didn't want something to happen then you wouldn't have dressed like this." She then put her hand on my back and snapped the back of my bra.

I told her that she didn't understand, that we really couldn't have sex and that she was going to find this a waste of time.

She said "Oh, we are going to have sex, or at least I am going to have sex. I have had sex lots of different ways and you are going to satisfy me even if it kills you."

I replied "Oh shit."

When we reached my hotel I again tried to dissuade her saying "Really, this isn't a good idea."

Judy just took my hand and pulled me towards the hotel saying "Just because you dress like a sissy doesn't mean you have to act like one. What floor are you on?"

We went up to the seventh floor and we then turned right to get to room 705. Judy told me to just give her the key and I did. She opened the door and we walked into the room.

"Well this place is lovely. Look, you have sliding doors separating your bedroom from the parlor. That is nice when you are here as a couple then someone can sleep while the other person watches the television. Well it looks like that is going to be wasted on you."

I headed for the safe and entered codes 1100, 1101 and 1102 which didn't work. Judy needed to hear the story so I told her about the keys in the safe and told her the device I had on couldn't be removed until I got the keys out of the safe. As I explained my problem the digital readout on the safe began the 15 minute countdown. I explained that part of the problem too.

Her response was "I want to see this device. In fact, I want to see everything you have on. Open that blouse and let me have a look." She sat on a chair and indicated with her hands that I should open my blouse.

I hesitated and then I turned so my back was towards her and I opened my blouse.

"Well that's really precious you being all shy and all like that. But I know that you are wearing a bra so why don't you just turn around so that I can see it."

I took a breath and closed my eyes and held the blouse wide as I turned. I expected laughter but heard nothing. I finally opened my eyes and saw Judy looking at my chest.

She finally spoke, "Ok, first of all I love the brassiere. Not many men could pull it off but on you it looks good" smiling as she spoke. "The belt is also very nice. But you have way too much hair on your chest; you should get your chest waxed. Also, you need some tits. Don't you have some socks or something that you can use to fill out that bra?"

I said "Oh I have something better than socks, take a look in that dresser, third drawer down," as I pointed directly at the dresser.

Judy looked in the third drawer and pulled out my breasts and tossed them at me. Then she started examining the other drawers. I tried to stop her but she was too far down that path.

Judy made comments as she examined the material in the drawers "Hey look what we have here. My you are a naughty boy aren't you? Oh, I have one of these and one of these. I sure don't have one of these."

Judy turned and saw that I had inserted my breasts and said "Now don't you look better. I still need to see that thing between your legs. Don't keep me in suspense, pull down your pants."

I slowly unhooked my belt and unbuttoned my trousers and bent forward pulling them down. I took off my shoes and stepped out of my pants.

Of course Judy had some choice comments "What is it with you guys and your fucking garter belts? Don't you know they went out in the fifties? I swear you start out wearing your mother's lingerie when you are ten years old and then you are stuck in that time warp. I'm surprised you're not wearing an 18 hour girdle, or a corset with a petticoat. Hey look, the fifties just called they want their clothes back."

Judy continued "I like the panties and matching bra. I have to get a picture of this." I objected but she said she wouldn't include my face; she just had to get a picture so her friends would believe her. She took out her phone and took some pictures while I stood there with my hands covering my face.

Judy was now interested in my chastity "Now pull down your panties. I want to see how that thing works."

I pulled down my panties and then Judy started to laugh. "You mean you did this to yourself?" She then grabbed hold of the cage and moved it back and forth testing the security. She walked around me and I felt her fingers moving up the metal rod into my anus.

Judy just needed to know, "What is on the end of this thing?"

"It's a ball" I replied.

Judy then came around in front of me and put her hand on my cock cage and then played with my balls.

"Does it hurt when I play with you?" she asked.

"No, it feels good, but I can't get hard, I am restricted" I replied.

Judy then took more pictures of me and a lot of pictures of my cock cage. She had me step out of my pants and spread my legs so she could get a picture from the floor between my legs. She took a picture of my behind while I was bending over. Finally she took a selfie with her standing next to me and me covering my face. My brassier and penis cage were plainly visible.

Judy then said "Well let's see what fun we can have. Pull up your panties and pants and tuck in that blouse and let me get a good look at you."

I did as I was told, buttoning up and tucking the blouse.

Judy responded "Now that you have tits, you are not half bad. Turn around slowly so I can take it all in. Keep turning."

I turned a few times and she told me to hold my hands to the side with my fingers pointed away from my legs.

"You know from the neck down you are almost passable. Your hips are too thin and you don't really have a good booty but those can be fixed with pads." She found my cosmetics drawer and she took out some face powder and mascara and lipstick and eyeshadow and she shooed me off into the bathroom to fix my face.

In the bathroom I took off my blouse and started working on my face. I wasn't good at this but it wasn't for lack of trying. All the while I could hear Judy rummaging through my things, periodically exclaiming "Oh this is nice. So why didn't you wear this? Boy I wouldn't be caught dead in this."

I was working on my lips as Judy came in with a blouse and a skirt and my black high heel boots and a selection of jewelry. "Here, put these on. I think you will look better. Also, you said before that you weren't really looking for a gay experience, but I notice that you have a couple of very realistic dildos, balls included. One has a suction cup and the other one fits onto this harness. Just saying, it all looks kind of gay to me."

Judy continued "Look what else I found, this brand new toy that is still in its package. It says here that this is 'An anal training kit' and it has never been used. I would try this out on you but the proper location is currently occupied."

Her next revelation was "Look what else I found, a nice selection of condoms, flavored too. I don't know what you expected to do if you had brought a guy back with you because you would still be in the same situation, a locked up cock and ass. Oh, wait, yes I do. Well, keep at it and come out when you are ready. I'll give the safe a few tries to see if I can crack it while you are making yourself beautiful."

For the umpteenth time my face was as red as it could be. I called out to her "Try 1103, 1104 and 1105." Judy just grunted.

I finished my face and put on the clothes that I had been given. I received no new underwear so I guess that my circa 1950's garter belt would have to do. I put on my black pointed collar flare sleeved semi-sheer blouse with pleats and front buttons. I had mentioned to Judy that this blouse came with a camisole top but she told me that I wouldn't need the cami.

I like to buy long sleeved blouses to hide the hair on my arms. Hi necked blouses are also desirable. I buttoned the blouse right up to the collar to conceal my chest hair.

For my skirt she chose my black and white floral flare skirt. Flowers are printed on the skirt and there are alternating black and white horizontal lines. I think the horizontal lines make my ass look bigger, not something that most girls need. My skirt sits 3 inches above my knees and flares from the waist. The waist has no elastic, just a back zipper and a hook and eye closure. I had to send back the skirt two times before I received one that fit properly.

My shoes were black boots with a 3 inch chunky heel. The girl in me cried for my 5 inch stiletto pumps with locking ankle strap, but I wasn't choosing my footwear. I have no trouble walking in the 3 inch chunky heel but the 5 inch stiletto is very challenging. Although, since I was only walking 20 feet what did it matter?

I added a chunky green mint & crystal statement necklace. I added on my silver hoop earrings. I don't have pierced ears but I have cut off my earring posts and I super glue the earrings to my lobes. It really looks like my ears are pierced.

I added an ankle bracelet, a tiny silver chain with interlinked hearts. I added a silver bracelet accessorized with a silver bisexual pendant on one wrist and a bracelet with a transgender pendant on my other wrist.

The ring on my right hand was in the shape of a pair of bikini panties. On my left hand I wore what looks like a princess tiara, containing numerous cubic zirconia stones. All of my jewelry is cheap crap. The princess tiara ring is the best of my cheap crap.

The final touch is my wig. I don't know if Judy had noticed that I had brought one but I had it sitting in the bathroom on a folding wig stand. I own three wigs and I brought my brown bob wig. The cut is angled longer in the front than in the back. It has blunt bangs which help hide my manly eyebrows.

I made my final wig adjustment, checked myself over and told Judy that I was coming out.

As I entered the room Judy said "Well don't you look special. You should have nude legs, and if you had to dress like that every day you would prefer pantyhose. Walk over to the chair and sit down."

I walked over and slid my hand behind my skirt as I sat down as daintily as possible. I crossed one leg over the other which isn't that easy with the equipment that I had to contend with.

Judy looked at me closely, said that I would do better with my cosmetics if I wore them daily and even said that we should go to a store so she could pick cosmetics that better matched my complexion.

Her next comment was "Well you look like a girl, let's see if you can act like one. Get up and come over to me and kneel in front of me."

Well she was getting right into it. No mention of my sexy legs, my pretty jewelry or my beautiful eyes. It looks like I was going to do the only thing that I was equipped to do, eat pussy. I was okay with that.

I knelt down in front of her. She pointed at her crotch and it was obvious what she wanted. I was breathing harder as I unbuttoned her pants and pulled down the zipper. When I pulled her pants down I saw that she had something sticking out of the top of her panties. I pulled down her panties and saw that she had put on the harness and I was now staring at my six inch dildo shaped like a penis.

I know this penis very well. I have sucked on it many times and it has also been up my ass. The penis is very realistic with balls and veins along the side. Judy stepped out of her shoes and pants and told me that I was going to suck it like the good little cocksucker that I was. I didn't have any problem with that since I have given that cock many a blow job, usually on my knees and usually wearing a bra and panties. The only difference was that this toy was now attached to a person instead of being attached to a mirror.

I began by licking the head of the penis. At that point Judy stopped me and put a condom over the penis. She said that she didn't want to get any diseases from me. I looked up at her and smiled and then went down fully on the penis. The condom was strawberry flavored, my favorite.

I'm sure Judy was surprised that I was able to take in all six inches, with my lower lip hitting the balls. This was due to the significant amount of practice I have had with this penis.

I went up and down on her sucking the head then playfully letting go of the cock, licking the head then going down to the balls and licking the balls, looking up at her as I slowly tongued my way back up the penis, to the head where I would open my mouth and suck the penis all the way down to the balls.

Judy said "You are getting way too much enjoyment from this, and I'm getting almost no enjoyment at all. I need to take this thing off" and she removed the harness.

Judy then sat down on the edge of the bed and said "You can suck cock so you are great with men, but a real woman knows what to do with a vagina" and she crooked her finger indicating that I should come to her.

I stood up and walked towards her in as sexy a manner as I could. I then knelt in front of her and starting kissing my way up her leg. I heard her sigh as her knees parted. I continued to kiss, nibble and lick her thighs getting ever closer to my goal.

I finally reached the outer lips of her pussy and began licking each side slowly. She was already dripping from her cunt. Her outer lips relaxed and I turned my attention to her inner lips. Her clitoris was engorged and my lips and tongue attended to this area.

I heard Judy sigh as she flopped down onto the bed. I continued to assault her clitoris and then she trapped my head with her thighs and I heard her cry out "Yes! Yes! Yes!"

Judy then relaxed her knees and pushed my head away saying "No more, god I needed that. God you were great. You are as good as a woman. You should get your thing cut off or at least keep that box around it. If your penis was free you would have been done 20 minutes ago and I would still be looking for sexual release."

I told her "I wish I could get that safe open then I could get more enjoyment for myself."

She leaned down and kissed me on the lips and told me that she had an idea that I would find very exciting. She told me to go refresh my lipstick. I went to the bathroom and redid my lipstick and worked a little on my face and went back into the room.

Judy then told me her proposal. At first I rejected the idea but she persisted and eventually I saw that she was correct. We got everything in shape and initiated her plan.