Time for a Change

Instead, Jason came around to my side of the counter and looked me in the eye, "You're a great person Chris and we are glad to have you as a new friend. I'm sure you're great at what you do."

To my surprise he pulled me into a hug. I instantly forgot about my hardon and let those big arms wrap themselves around my body. It was the first human contact I have had since my divorce. His body was rock hard and soft at the same time. He had a business suit on and he smelled really nice, light citrus smell I think. Then he kissed the top of my head and walked out the door. I knew my cock was pressing into his thigh but there was nothing I could do about it. I'm sure he had to have noticed it but the great guy that he is, he didn't mention it.

I left for my business trip to Minnesota. I arrived at my destination and began my routine, checked into the hotel, unpacked, turned on my computer, ordered room service, and hoped into the shower to wash the flight off of me. I wrapped up in a hotel bathrobe just in time to hear room service being delivered. I never felt uncomfortable before being naked in a robe with room service delivering my food, but this young man was really cute. I was actually checking out his ass in his tight pants. I found myself looking for signs of his cock from the front of his pants. I was becoming obsessed with the male physique.

I ate my dinner and began doing some work. My mind wondered to Jason and Stephen again, my cock got instantly hard. I shut work down and brought up the internet. I searched for an adult porn store, none close. I put on some casual clothes and went walking. The cool night air would do me some good. I found a convenience store and started to search through the magazines. A muscle magazine, not porn but it reminded me of Jason and Stephen. As I walked down the aisle I struck pay dirt, porn. The usual Penthouse, Playboy, then there was some more risqué magazines, gay, bi, bdsm, tranny, and lesbian.

The doorbell rang out and now there were others coming into the store. I grabbed a couple of the magazines without even looking, placed the muscle magazine on top and went to the counter to pay. The guy behind the counter rang the purchases up and told me it was $32, I tossed him my credit card and wanted to get out fast. He asked if I wanted a bag, I quickly told him I did. I could feel everyone in the store staring at me, but after looking around nobody could care less. I grabbed my bag and ran out, and all the way back to my room.

I opened the door to my room and threw myself on the bed. My heart was racing. I started to calm down as I kept telling myself that nobody even knows me in this town. I laughed at how foolish I felt and dumped my bag on the bed. I flipped open the muscle magazine, the pictures of those solid bodies with just a little Gstring covering what looked like nice packages. I began to focus on the outlines of their cocks. Some guys were clearly packing and some were half hard or very large. My own cock was hard and I stripped out of my clothes.

I looked through the pages while slowly stroking my cock. I picked up one of the other magazines, 'Sissy' was across the top. I started flipping through the pages, stories and pictures. I froze on one page, a man dressed in lace panties with a little cock sticking out the side, the man had on a bra and was jacking himself off looking at a woman on the bed getting fucked by a good looking guy. Across the top of the page was written "My husband My Sissy Slut".

I started reading the story around the picture. It was about a man that got off on watching his wife get fucked by other men. His small cock could never please his wife so she took on lovers and made him watch as they fucked her. I turned the page to continue the story through a series of pictures with bubbled captions;

The first slide had the man licking the other guy's ass as he fucked his wife. The bubbled caption from the lovers mouth was him screaming out in orgasm "Lick that hole you sissy boy, make me cum in your wife's pussy."

The next slide was the sissy eating his wife's cum covered pussy and bubbled captions "Ya boy eat all of my hot my cum bitch."

The wife's caption "His cock was so big and hard baby, you'll never satisfy me like he can. Now clean up my lovers mess and suck his cum out of my pussy. Make me cum again." She had a handful of his hair and forcing him to eat her pussy.

The next slide had the couple sitting against the headboard and the sissy was sucking the guys cock with captions, "Good sissy boy, clean my cock, lick off all of her pussy juice and suck that cum dripping off the top."

The wife said "You can't even see his little dick in those lacy panties, he makes a better girl than a lot of girls I know."

My hand was working my cock hard. I felt the familiar surge in my balls as my body stiffened. My body flew back against the bed and my cum shot all over my chest. I quickly squeezed my cock forcing a big dribble of cum onto my finger and brought it up to my mouth, "Ya sissy boy clean up your mess, clean up all the cum off his cock." I licked my finger like a cock and enjoyed the feel of my cum in my mouth.

I never thought of me in that way, but I did have a hairless feminine body, I bet I could pull it off. I fell asleep waking to my alarm the next morning. I hurriedly got ready for work and headed to the clients office. I met up with the local sales rep in the area and we did our dog and pony show. The entire time I was thinking of what I wanted to buy when I was through here. I was distracted in my thoughts until I felt the hand on my thigh give a squeeze. I about jumped out of my skin. I recovered and spit out enough techno stuff to make everyone nod their heads. I knew they had no idea of what I was talking about but it sounded impressive and they bought off on it.

We finished up and I declined dinner with the sales rep by telling him I wasn't feeling well and wanted to get back to my hotel. What I really did was hit the Great Mall of America and headed for some shopping. I went into one of the big name brand stores and felt it was too crowded. I walked out to the directory and found Victoria Secrets on the first level. I took a deep breath and walked in. 'Nobody knows me here' I kept saying to myself. I looked through a few things and rubbing my hands against the silk and lacy garments when a sales lady came up to me and asked if I needed some help.

I'm sure she's heard this a million times when I told her I was here looking for an anniversary gift for my wife and that she was about the same size as me. She smiled and began showing me some very provocative panties. She was even so bold as to hold them up to me and telling me that they would look nice on your "wife". She didn't make the air quotes but her voice said it all. She kept showing me size 4 to 6 things. She showed me some one piece body suits, some bra and panty sets, and some baby doll outfits. I wanted to buy a Kimono and bra and panty set but didn't want to spend over $100 for it just to try out.

I believe the sales person caught onto my apprehension as she leaned in closer to me to whisper "You know if you don't want to spend a lot of money to try this out then head up to the third floor to Spencer's, you can get nice lingerie up there cheaper and maybe a few toys as well to help break you in. I'm sure you will look very sexy in whatever you buy." She winked at me as she patted my butt and walked away.

I was embarrassed that she saw through my rouse but was hard as a rock and even felt a wet spot in my pants as I started walking out the door. I looked around the mall searching out a way to head upstairs. I almost ran to the escalator and headed up to the third floor. I walked into Spencer's. I felt like a kid in a candy store, and ADULT candy store.

This store had everything I wanted. I just had to get the nerve to go through with it. The store was fairly empty. The clerk was a girl with spiked hair, a ton of makeup and piercings in her ears, nose, lip, and eyebrow, very punk rocker look. I walked up and down the aisles avoiding direct eye contact with people or what I was looking at. The door chimed and the other people in the store left, it was just me and the punk rocker girl.

I was looking at lingerie again, wanting to pick something out fast, pay for it, and leave. The girl behind the counter stood behind me, I didn't hear her until she said "May I can help you find something?"

Her voice was deeper than I expected but still scared the living hell out of me. "Oh yes, I was just looking for something for my wife, it's her birthday." I tried to sound non-challan and confident like I do this all the time.

She could care less about my lame excuse, "Hey man I don't judge I just sell shit. You would look good in this." She held up almost the same baby doll outfit from downstairs at less than half the price.

"You look like a beginner, what's your budget?" She said matter of fact attitude.

"Um, I don't really have one. I'm not really sure what I'm looking for." I stumbled with the words.

"By the looks of you, and the way you were looking at toys for men, I would say you're a beginning sissy and want to start checking out your submissive side. You probably haven't tried anything bi or gay and wondering which category you fit into. I think you will make a hot pussy boy. Try out this anal kit, it has a little of everything to start off with. You'll need this douche to clean yourself out; you don't want to make a mess. You'll need some good lube, especially if you're a virgin. Use lots of lube. Here are some vibrating toys for your boy pussy" She loaded my basket up and walked back to the counter.

I followed like a lost puppy. She rang up the contents of the basket which came to a little over $250. I flipped out my credit card and paid for my purchase. Then she turned around and grabbed a tube off the shelf and tossed it in my bag. "This ones on me sweetie, I want you to enjoy yourself. And if you need some help just give me a call I'm off at ten." She tossed a card in my bag as well.

I walked out of the store and straight to my car before people could see my bag. I don't even remember the drive back to my hotel. I called room service and ordered dinner. Just before I hung up I told them I forgot my shaver and could they send up a disposable one? I wasn't sure what do to, but I started by undressing and getting into my robe. I opened my bag and pulled out my new outfit. I placed my toys out on the bed and started to open the packages.

Before I knew it I heard a knock at the door and a voice "Room Service". Crap, I quickly folded the blanket back over my stash and opened the door. The same cute guy came in with my tray. He bent over to place the food on the little table by the window. I could tell he hesitated for a second before standing upright. I looked down at the trashcan and noticed the anal kit box was in plane site. He turned to me "Will that be all for you Sir?"

I looked down, embarrassed, "Yes that will do it." I handed him a $5 tip as he walked past me.

"Oh I forgot, here's the razor you asked for. If you need anything else please call the main desk and ask for Andrew." He winked and walked out.

I was flattered and shocked at the same time. I ate about half the meal before my excitement got the best of me. I headed into the bathroom, grabbing the enema box on the way. I dropped my robe and looked at myself in the mirror. I opened the box and read the instructions. I filled the bulb with warm water and attached the wand to it. I got on all fours, reached back and tried to insert the wand into my ass. The angle was wrong and it hurt when I tried to push it in. I then grabbed the complimentary little bottle of cream and rubbed some onto my hole. I let my fingertip dip inside to test the lubrication. I squatted over the toilet and was able to get a better angle for the wand. I pushed the wand into my ass. At first it was uncomfortable, but as I pushed it in deeper and deeper it started to feel better.

When I thought it was in enough I started to squeeze the bulb. I felt the warm water enter my bowls. I kept applying pressure to the bulb and the water seeped into me. I wasn't sure if I could take the entire bulb's worth of water but I kept squeezing anyway. The pressure was getting intense so I pulled the wand out. Water immediately started to flood out and I pulled my hand away just in time. My bowels emptied out fast.

I read the instructions again and it said to add a mild soap for freshness, and to hold the water inside the bowel for five minutes. I repeated the process but didn't put so much water inside. I pulled out the wand and was able to hold the water in. I waited for a few minutes and released the water. I repeated the process and the third time the water was clear.

I jumped in the shower and let the hot water cascade down my body. Then I soaped my body up, starting with my left leg I began to run the razor up and down my leg. I didn't have much hair at all. I continue up to my crotch and didn't know where to stop so I shaved off my pubic hair. I just couldn't stop there as I went up my little trail on my stomach and the couple of hairs around my nipples. My armpits were easy enough with a few swipes. I bent over onto all fours, reached back, and ran the razor up and down the crack of my ass. I was hairless except for my head.

I toweled off my body and my sensitivity was on overload. I went into my room and grabbed the lingerie. My hands were shaking as I slipped the g string on, then the bra which I hooked in the front and spun it around. I pulled it over my nipples and gave them a squeeze. My head was swimming. I laid on the bed and rifled through my other treasures.

A vibrating dildo, a vibrating cock ring, a bottle of lube, and some prolong cream. That is what was thrown in the bag by the store clerk. I found the card and read it, "I'm off at 10pm. If you have any problems with what you bought call me and I will come by and show you how to use it. B." Her phone number was on the bottom of the card.

It was already 10:10pm, crap. I picked up my cell phone and started to dial the number. I hung up. I dialed again and hung up before it connected. I did it a third time and it rang before I hung up. I was too nervous. I couldn't go through with it. Then my phone rang, she called back. I let it ring four times before I answered, "He el lo" I squeaked out.

"Don't hang up on me again. I knew you would call. You're lucky I was just getting to my car and was going home. Where am I going now?" I heard her voice stern and confident.

"Um, St Paul Hotel, Room 305." I blurted out.

"I'll be there shortly. Have on that pretty outfit when I get there. I'll show you how to use all of your new toys baby." She hung up.

What did I get myself into? I looked at myself in the mirror, dressed in women's clothes, a bra with nothing in it, panties with a slight protruding nub of a cock poking out. But the material felt so...sexy, made ME feel sexy. Nearly an hour later I hear the knock on the door. My blood goes cold. I can't move to answer it. Maybe she'll go away, it's not like I would see her again. Another knock on the door and I find my feet moving to answer.

"Don't leave me hanging, its rude. Now turn around for me, let me see how you look." She walked caring a bag with her store logo. She went to the chair and sat down. She started to take off her black army boots, and leather jacket. She took off her T-shirt. She had no bra on and perfectly round B cup tits with large nipples poking straight out. She stood there wearing only a plaid skirt. My cock sprang up, to what little it could. Well at least I know that a woman's body still turned me on.

She stepped up to me and kissed me. Her tongue flew into my mouth and I felt the ball on her tongue swatting at the roof of my mouth. She pulled back and pushed me onto the bed. "You're so fucking sexy. I'm going to make your dreams come true tonight." Her body fell onto mine and we made out.

Her hand massaged my cock through my lacy panties. "Your cock is so tiny, I love that. Sissy boys don't need big dicks; it would make you too much like a man. I like by boy's cocks small and their pussies tight. Do you have a tight pussy baby?" With that I felt her finger feeling around my puckered hole.

She took her hand away and fed me her finger. I sucked on her finger as she moved it in and out of mouth. I was blowing her finger. She was face fucking me with her finger. I was ready to blow my load. She pulled her finger out of my mouth and placed the wet digit against my hole. I felt my saliva being rubbed around my hole. She looked into my eyes before she forced another hard kiss on my lips and shoved her finger up my ass. I moaned into her mouth as she wiggled her finger deep in my hole. "Oh ya that's it baby moan for me, tell me how much you love it, tell me you want more. Beg me to take your cherry." She bit my lower lip.

I moaned and whimpered "Yes, Yes, take me. Show me, teach me."

She reached over to the nightstand and grabbed the small vibrator, lube, and the prolong gel. She used the prolong gel first and rubbed it all over my cock, balls, and even my hole. "This will numb you a bit and make you last longer. I don't want you shooting your load until I tell you, understand?"

I lay on the bed just nodding my head and trying not to cum. My cock and balls felt cool, my hole started to burn a bit before it stopped. She blew air all over my cock and balls. Then when I felt her blow on my hole I felt an electric shock race up my body.

"Ready to play baby?" She whispered in my ear. She licked my earlobe as I felt the tip of the vibrator press against my hole.

She breathed in my ear again "Pain and pleasure" just before she bit down on my earlobe and shoved the vibrator up inside of me. My back arched up to avoid the intrusion but she held the vibrator in place. It was only a 5 inch one and not too thick, but it was larger than any finger.

"SHHHHhhhh, relax baby. It will feel really good in a moment. Breathe through it." Her calming voice relaxed me and my back came back down onto the bed. She turned on the vibrator and my entire body shook.

She began to slide it in and out of my hole while still licking my ear and southing me. Every stroke made me want to cry out in pure ecstasy. She then moved her body and knelt between my legs. Her breasts bouncing above me made my mouth water. I felt pure lust in wanting to devour them. Suck on those nipples.

She grabbed my hand and pulled it to her breast. It was soft, so soft. Her nipple was in contrast hard as a rock. I rolled her nipple between my fingers. Her head went back. "Harder, pinch it." She pleaded with me.

I pinched her nipple and she leaned forward. Her face slammed down onto mine. Our lips locked. "Harder, pinch them, pull them. Harder, twist them." Her body was on top of me now, her hand pressing the vibrator as deep as it would go.

I was not expecting what happened next. She pulled out the vibrator, and what she pushed back in was bigger but felt good. Her hands came up, grabbed both my hands and pinned me to the bed. "Pinch my nipples NOW." She screamed.

Her hands were above my head. I pulled each nipple, twisting it at the same time. She plunged her COCK into me. I felt her long cock deep inside of me. Did she have a strapon underneath her skirt? She kissed me hard and I instantly wrapped my legs around her waist offering her full access to my boy pussy. Yes that's what I have a boy pussy. She started going in and out, fucking me like a real girl. We were both covered in sweat as our bodies tangled in wild hot sex. "Deeper, fuck me deeper. Oh My God, please fuck me, fuck me." I never wanted it to end.

I pinched her nipples hard, grabbing just the sensitive tips. Then I felt it as she plunged deep inside, her balls rested on my ass and I could feel her cock pulsing as she pumped me full of cum. She was a guy, at least a guy below the waist. She lifted her upper torso off of me "Surprise." is all she said before we kissed passionately.