After that first night I was so sore and satisfied, we continued with our strapon play doing it in every possible position: standing up, doggy, missionary, and sideways. She was really into it and loved talking raunchy. Then she stopped using the strapon altogether and shortly after that we stopped having sex for a couple of weeks.
I was getting nervous that she might be having second thoughts about the direction our sex life took. A few more days passed and I decided to bring up the subject.
"Honey is something wrong?" I asked.
"No, why what's up?" she replied.
"Well … it's just that we haven't … you know … for awhile," I stammered out.
She got this coy look and feigned ignorance, "We haven't done what baby?"
"We haven't played around for awhile and I was worried that you might be turned off or something like that," I was nervous about her response.
She stood and gave me a long passionate kiss saying, "I have my reasons for holding back for awhile. I want you really horny for this Friday because I have a surprise for you." I was getting hard as she grouped my ass and ran her tongue up the side of my neck.
"What's the surprise?"
She whispered, "If I told you that it wouldn't be a surprise would it? And no masturbating promise?"
I nodded in agreement.
By the time Friday came I was so horny I couldn't stand it. We had a couple of glasses of wine and relaxed for a while. She reminded me about her promise to dress me up to look exactly like a girl and I remembered.
She led me to the shower where I used a cream that took off all my body hair, when I stepped out I was entirely hairless except for the hair on my head. I enjoyed the smoothness of my skin as she helped me rub in a body lotion that left my skin soft and smelling nice. Next, she had me sit down and began to apply make-up as we had some more wine. I was amused at how I left lipstick on my wine glass. After she finished making me up she went to her closet and got out several boxes.
I was curious what was in those boxes. She opened one and returned with a long curly brunette wig that she secured on my head.
She said, "I settled on this color because it strikes me as a more slutty hair color than blond, later on we can try out blond too."
I couldn't see my self in the mirror because she had moved it so I couldn't peek until I was entirely transformed. I shook my head and remarked at how well it was attached.
She grabbed a handful of hair pulled my head back and said, "I can pull your hair hard and it won't come off plus you won't feel a thing."
She surprised the hell out of me by opening a box that revealed a pair of fake silicone breasts complete with nipples. She held them up, "Here's your tits baby. I decided to be generous because we both know how important it is to have a nice pair."
She applied a mixture of spirit gum and some other adhesive attaching both breasts to my chest she blended them into my natural skin tone with some makeup and stepped back smiling a wicked smile.
She pinched a nipple and looked at me saying, "Now you have tits bigger than mine baby." She leaned down and licked a nipple giving a little moan as she did so.
She walked back over to the next box and took out a black corset saying, "This will give you a girlish figure." She helped me get into it then laced it up. Next, she braced herself and told me to suck it in as she cinched it up tightly.
She stepped back and said, "Wow, you have an hourglass figure now complete with hips."
The other boxes contained lingerie: garter belt, black lace stockings, matching bra and black silk thong panties. I quickly dressed in the lingerie expecting that we would immediately start having sex.
She stepped back whistling and said, "Wow, you look soooo sexy – I told you I could dress you up to look just like a woman." With that she turned the full-length mirror around and I saw myself.
I was stunned into silence. My red lips opened into a seductive 'O' complete with a generous amount of shiny lip-gloss. I touched my breasts rubbing the nipples through the see-thru black lace bra. My hands roamed over my waist and bare ass.
I looked exactly like a slutty woman except for one thing – my cock!
She was watching me with intense interest and said, "You look exactly like a woman except for your big dick. You look like a shemale baby. The best of both worlds – you look hot!"
She handed me a black silk dress and a pair of heels. I slipped on the dress and stepped into the heels she said, "I want us to have a night we'll both remember for a long time. Let's get a hotel room so we can make noise without the neighbors hearing or worrying about being interrupted."
I thought about it for a second and said, "Dressed like this?"
She smiled and said, "Don't worry you are definitely passable as a woman. My only worry is that some guy will come along and steal you away from me." She said with a little pout.
I laughed and said, "You don't have to worry about that I'm all yours."
We piled into the car, she brought along some essentials for our stay, and off we went. She drove with purpose eventually going through a bad part of town where hookers and drug dealers frequented.
I asked, "Where are we going?"
She just smiled and said, "Don't worry trust me. You do trust me don't you?" I nodded.
We ended up at a questionable looking hotel she announced, "We're here baby lets go." She got out and I followed her she produced a key and let herself into a room.
I was surprised that she had a key and wanted to know why.
"I've been planning this for awhile I wanted everything to be perfect for you baby." She went to the kitchen and came back with two glasses of wine.
I finished mine in two gulps then we began talking.
"You look so hot dressed like a woman, so what would you like to do tonight baby?" She asked with raised eyebrows.
"Whatever you want to do honey. I want to fuck," I said.
I got a little head rush and commented, "Wow, how many glasses of wine have I had anyway?"
She tilted her head to one side, "Not nearly enough baby, don't worry it's not like you have to drive tonight."
Then she continued, "Since your dressed like a slut I want you to pretend that you are one. I want you to really get into it, so what do you say."
I was tingling all over as I said, "Oh yeah honey use me like a whore." I licked my lips seductively. She took my hand leading me to the living room.
She handed me a blindfold saying it would heighten the experience.
I put it on and she kissed me deeply.
Her mouth was replaced by a ball gag she secured snuggly around my head.
I mumbled surprise anticipating my question she said, "This way you can moan as loudly as you want or scream in ecstasy and no one can hear you – plus I want you helpless completely in my control."
She maneuvered my hands behind my back and secured them with handcuffs.
Next she pushed me down onto my knees and then over a bench.
She finished by securing my legs to the bench with some rope.
I heard her making noise and I was trying to figure out what she was doing.
A few moments passed she was making more noise being very busy.
She asked, "You love being dressed up like a whore don't you. You want to be used like a slut. You want your ass violated by a big cock don't you? (She loosened the ball gag)"
I said, "yesss."
She said, "I can't hear you baby. Tell me the honest truth what do you want more than anything in the world."
I said, "I want to be fucked."
The excitement caused me to have another head rush I was feeling very high. She moved behind me lifting up my dress moved my thong to one side stroking my ass softly applying a generous amount of lube which drove me crazy.
I said, "Oh yeah honey please I want it bad."
She asked, "What is it you want baby?"
I said, "I want a big hard cock up my tight little ass."
She lightly slapped my ass, secured the ball gag again, and said, "Since you asked nicely and look so cute I guess your ready."
She removed my blindfold and I saw her walk over to a video camera on a tripod I wondered where the heck it came from. She switched it off so that the red light blinked out.
She said, "Excellent, now that I have your statement that's irrefutable documentation permanently recorded its time for your surprise baby. You probably thought it was being dressed up like a girl but it's not. Want to guess what I have planned?"
Just then there was a loud knock at the door.
She looked at me saying, "Oh yeah, right on time baby."
She opened the door and I heard voices but couldn't see who was there my head was swooning and I almost lost consciousness.
She reappeared in front of me detached the video camera from the tripod and switched it on panning it around the room then pointing it directly at me.
She said, "Now boys this little slut likes it kinda rough after she's been warmed up and don't worry there's enough to go around."
I was in a surreal dreamland and was surprisingly relaxed and very aroused. I felt hands all over my body and fingers probing my ass I let out an involuntary moan like some eager slut.
I heard someone say, "C'mon bust that white ass!"
I felt pressure then something large thrusted into my ass. I arched my back and let out a cry muffled by the ball gag. A long slow push slowly forced every inch into me I felt it bottom out and the tingle of pubic hair. I clamped down hard on the large intruder with my anal muscles and I heard a man's voice, "Son-of-a-bitch this cunt is milking my dick with her ass muscles. You like that don't you bitch?"
I felt a hard slap on my ass and responded by wiggling my butt around.
The next memory I have was being free of the restraints straddling a black man wearing a ski mask bouncing up and down on his long cock while another took me from behind and pounded my ass hard.
I was doing a double anal penetration when a hard cock was rubbed across my lips.
I never had that much inside of me before and it was real too.
After that I faded in and out. I woke up the next morning alone with a splitting headache I staggered to the bathroom after a long piss I noticed a note taped to the mirror.
It was from her and said, "After all the excitement last night I decided to let you sleep it off. Give me a call when you wake up."
I called her up she asked, "So how are you this morning?"
I said ok except for a headache.
She said, "I left some pills on the counter and there's some juice in the frig." She could tell I was reluctant to take any pills especially after being drugged, "Don't worry baby they're safe to a take. I gave you something extra last night because I wanted you relaxed and compliant. Plus it gives you an excuse if you have any regrets … well do you have any?"
I said, "No, from what I remember it was wild I enjoyed myself. I can't believe I actually did those things. I'm just a little worried I guess."
I decided to take the pills the juice tasted wonderful.
She asked, "So you're not all freaked out or anything right?"
I said no just worried.
She asked, "What are you worried about?"
I said I was worried about people finding out about what I did.
She replied, "Don't worry those guys don't know your name or even what you really look like and you will never know who they are because they all wore ski masks. So you worried about anything else?"
I said diseases.
She assured me that they all wore condoms and we practiced safe sex so it was cool and she asked again if anything else worried me about last night.
I reluctantly said, "I'm worried you think I'm gay."
She laughed and reassured me again by saying, "Your not gay just kinky and just because you like to get fucked in the ass and role play it doesn't commit you to a lifestyle unless you want it that way. Even if you decide that your bisexual that's nothing more than just acknowledging what everyone else feels but is too afraid to admit."
Relieved I said, "Thanks for everything honey I really appreciate it honestly I do. What about the video tape?"
There was a long pause and she said, "Well now baby that tape is mine and there is only one copy of it."
I said, "Copy?"
She continued, "Yeah I left you the only copy so you could watch it there in the hotel. As a matter of fact all you have to do is push play."
I pushed play and saw myself on the TV being pumped full of big black dick. I stammered, "Oh my god."
She giggled and said, "You know what they say once you go black you never go back."
I asked, "How many?"
She replied, "You took on five well hung black guys last night baby, so how do you feel? Sore or what?"
I continued to watch the TV and said, "You'll be surprised but I'm not all that sore I guess you did a good job of breaking me in."
She said, "So was I right or was I right. Doesn't the real thing feel better than plastic?"
I said it felt good but I would still enjoy her strapon play.
She said, "Good. I wasn't able to fuck you last night because you were just a little to busy but I can't wait until I see you cause I got myself a new larger strapon and I can't wait to use it on you."
I had a raging hard on I asked, "What now honey?"
There was a pause as the effect of the pills began to take effect.
I asked, "I thought those pills were safe to take honey I'm starting to space out again."
She said, "Don't worry it won't be like last night you'll just get real high is all. Now as for what's next on the agenda I have a couple of ideas."
She stopped as if in deep thought I asked her what she had in mind. "I have the room reserved until Monday and it's only Saturday morning so you could stay and take advantage of it."
I told her that I was up to it and wanted some details.
She said, "The guys last night expressed an interest in seeing you again I could set it up so that they drop by this afternoon for you and even bring some friends. Or if your feeling really brave you could turn a few tricks. I left a new outfit for you hanging in the closet and there's some makeup in the bathroom for you to freshen up with."
I said, "Turn tricks?"
She countered, "Yeah dress up stand on the corner and find some Johns to suck or bring 'em back to the room to fuck you. I have it on authority that you'll bring in some serious cash."
I replied, "No I can't do that."
She laughed and said, "I can force you to do it baby."
I said, "What!"
She continued, "I have the original tape and as long as I do I can pimp your ass out as I see fit!"
I heard a knock at the door.
She heard it over the phone and told me to answer it because she had sent someone over to get me up this morning before she knew I was already awake.
I opened the door and there was a black guy who walked in giving me a slap on the ass as he passed me by.
She told me that he was here to give me a little wake up and I was to keep talking to her on the phone until he was gone. She said I was to do exactly as I was told or else. He was sitting at the dining room table drawing out white lines of what appeared to be cocaine.
He motioned me over to the table and handed me a rolled up bill.
She asked what was going on and I told her.
She said take the bill and snort as many lines as you can.
I kept the phone pressed to my ear as I snorted up several lines.
He was behind me and bended me over the table lifting up my dress and began jabbing his cock between my cheeks.
I moaned out loud and she told me to describe everything that was happening which I did.
He pumped my ass severely finally grinding against my butt with his huge cock twitching inside me.
He slipped out of me and pulled up his pants and just walked out leaving a small mound of cocaine on the table, a couple of more lines, and a used condom.
She giggled and said, "Now you're a genuine coke whore baby how do you feel?"
I was very high and replied, "I feel great honey."
She said, "Now get that fucking ass out there and make me some money bitch!"