Miss Jennifer Fucks Little Tiffie

The Saturday after Miss Jennifer had her boyfriend fuck my pussy/bottom, she called to me while I was doing her laundry and told me to come to her room. As I entered, she told me to come and stand in front of her, where she was lying on her bed.

I was, of course, dressed like a proper little housewife, with my pink lace bra stuffed with my big 54DD falsies, matching pink lace panties, sheer suntan nylon pantyhose and a pair of brand new black patent leather high heeled pumps with adorable hot pink soles that my wife had allowed me to order online from Shoe Dazzle. Over my lingerie I wore a very short black skirt that barely reached an inch or two below my bottom and a frilly black lace blouse that showed my pink lace bra almost as if I weren't wearing a blouse. As always I was wearing eye shadow -- three shades of sparkling pink -- heavy black mascara and a sparkly pink powder blush, with big gold hooped earrings and my favorite Amber Nude perfume, and a long golden blonde wig that fell almost to my waist.

"Hmm..." she said, looking at me, her eyes traveling up and down all over me. "I see you're dressed properly, my little sissy housewife." She nodded, then continued, "And very slutty, of course." She shook her head in disgust.

"Yes, dear. Of course. I...I always have try to be a good little wife for you, to dress the way you like me too." I paused uncertainly, then went on, "Um...you...you always have me dress up as a slut, mistress, so I thought that was the way you want me to be."

She sighed. "Yes, I guess I do, but if you're going to dress up as a slut, then you need to be treated as a slut, don't you, Tiffany?

"Yes, mistress," I answered, blushing and looking down at the floor. "I am a slut, Miss Jennifer, and I want to be treated as a slut."

She giggled and nodded. "And you did love having Jamal fuck you, didn't you, Tiffany? You loved having him slamming his cock in your little pussy/bottom, and then having him shoot his cum all over your face, didn't you?"

"Yes, mistress. I loved having him fuck me like that. Is he...is he coming over to fuck me again tonight?" My voice was trembling, but I knew inside that I really did want to have a cock in my pussy/bottom again. It was just that Jamal's cock was so big, and he'd been so rough when he fucked me. I was afraid he was going to hurt me again if he came over.

"Well, don't worry, little girl. Jamal's not coming to fuck you tonight. But we are going to go out and let me buy a nice strap on dildo, and then I'm going to fuck you in that horny little pussy/bottom of yours. How does that sound, sweetie?" She giggled again.

"I..I'd love that, Miss Jennifer. I'd love to have you fuck me with your dildo."

"Good, now go get dressed to go out. I'm going to take you with me to an adult toy store where we can buy a nice big strap on dildo that I can fuck you with." She paused. ""So, let's see. Go take off your skirt and blouse. You can keep on your pink lingerie and those suntan pantyhose make your legs look so feminine, but I want you to change into those hot pink platformed pumps that you love so much. Those pumps with those cute little pink denim short-shorts that I let you buy at Frederick's of Hollywood will really show off your legs. Then wear your biggest whore hoop earrings, and come back here. No falsies and no wig -- just your normal little boy's haircut. That should look completely ridiculous with all your makeup and those big hoop earrings. And I'm sure that your pretty pink lace bra will look very pretty.

"That sounds perfect to me, don't you think?" she grinned, laughing softly at the expression on my face. "You'll look like a complete sissy girly-boy who just likes to dress up as a girl. I think that will be just adorable. I mean -- we do want them to know that you're a boy, but just a boy who wishes he were a girl, right? Dressed up like that it will be obvious that you're just a little sissy boy, a little faggot who wishes he were a girl, but isn't really a girl, which is just what I want. I know you just can't wait to show off those pretty smooth shaven legs of yours in nylons and those little short-shorts." And she laughed out loud.

"Now shoo! Go get dressed up so we can go shopping and find a nice adult toy store where you can pick out get a big strap on dildo that I can fuck your sweet little pussy/bottom with. Go on, go change, then come back and let me see how you look. Oh -- and bring your pretty little pink purse with all your makeup in it. And remember, no wig sweetie. Just brush out your hair so it doesn't look all mussed up from your wig and you'll go like that. And no falsies in your bra, I want to be sure everyone can see that you don't have any boobs, just a flat sissy boy's chest."

I, of course, did exactly as she had commanded. I stripped off my skirt and blouse and wig, then slid those sexy little pink denim short-shorts from Fredericks up over my nylons and pink spiked high heeled pumps, then went back to her. Even though she always kept me dressed up as a girl, she made me keep my hair in a regular boy's style, so that when she wanted to completely humiliate me she'd dress me up in a super feminine outfit with oodles of makeup and perfume -- but not let me wear a wig so that with my boy's haircut it was obvious that I wasn't really a girl -- just a boy dressed up as a girl who wished he were a girl. As much as I loved looking like a slut and a sissy, I could hardly believe how ridiculous I looked when she did that to me.

My makeup made my face look extremely feminine, but without my wig and with the cups of my bra empty of my falsies, I was completely flat and that together with my short boy's haircut was completely humiliating.

After changing I hesitantly went back to my wife's bedroom, carrying my little pink purse which was completely filled with all my makeup and knocked on the door.

"Come in," she responded quickly, and as I entered, walking in small little steps because of my 1 ½" platformed 6" high heeled pumps, she commented, "It took you long enough." Knowing that I wasn't expected to respond, I went around the foot of her bed and came to stand in front of her.

Her eyes flicked up and down over me, and she grinned, chuckling. "Well, you little faggot, you definitely look ridiculous. With all that makeup, your earrings and high heels, and that pretty pink bra and those adorable short-shorts, you obviously love dressing up as a slut." She laughed. "But without one of your pretty blonde wigs and without your falsies it will be very obvious to everyone we meet on our little shopping spree that you're really just a sissy boy who wishes he were a girl, won't it?" And she shook her head. "And before we leave I think you need a bit more makeup, sweetie. I'd like to see you put on another coat of mascara, and some more perfume and blush -- just so you look as pretty and girly as possible."

I opened my purse and took out my mascara, thickened the black mascara on my lashes, then added blush and perfume and looked to her for approval. "No," she grinned, shaking her head. "More mascara, I think, and more of that pink blush on your cheeks. I want you to look like a complete and total slut tonight." And so I added two more coats of mascara, knowing that so much mascara truly did make me look like a cheap whore, then put more blush on my cheeks and looked up at her.

But she shook her head. "No, little sissy. More lipstick and lip gloss now." Putting on lipstick was always one of my favorite things, so I happily did as I was told, adding two more coats of pink lipstick and a shimmering pink lipgloss until she finally approved.

My lovely wife laughed at me, shaking her head. "That's just fine, sweetie," she said. "You look so absurd, so slutty, such a sissy -- I'm sure everyone will laugh themselves silly when they see you. Now come along. Let's go find a big strap-on dildo for me to shove up inside your little pussy/bottom."

She was dressed fairly conservatively, with black slacks and blouse, and fairly low 3" heels, but I of course looked ridiculous in all my girly things, but my short hair and flat chest. But I couldn't help wondering...was she going to take me out just wearing my pink bra, with nothing over it? Then to my surprise she took out a small bag from beside her chair and handed it to me. "Open it up, sissy. I just know you're going to love it."

I did, and my lipstick covered lips opened in shock. It was a very light weight white tee shirt, very tight and not quite long enough to tuck into my pink denim short-shorts. On the front and back in hot pink lettering were the words "I love to dress up as a girl, but I'm really just a little sissy boy!" on both the front and back, and decorated all over with a design of hot pink lipstick imprints, as if it had been kissed again and again by a girl wearing hot pink lipstick.

I gaped at her, but she just laughed and said, "You're so sexy looking all dressed up like that with all your makeup, nylons and high heels that I wanted to be sure everyone knows you're not a real girl. Now put on your sissy tee shirt for me." As I did as my lovely wife commanded, I could see in the mirror that the lacy cups of my hot pink bra showed clearly through the light weight tee shirt, and pushed against the lightweight fabric so that the outline of the cups of the bra and even the bra straps were very obvious. I couldn't believe she was making me go out dressed like this.

When we got in the car, she ordered me to unzip the front of my jeans and take my little pee-pee which was as always encased in a cute little pink rubber out of my panties, then she reached over and touched it, playing with it idly as she drove. She almost never touched my pee-pee anymore, except of course to spank it, so I immediately got a hard on -- although since my pee-pee was so tiny, it still wasn't very big, hardly bigger than my wife's little finger. She played with it as she drove, keeping it rock hard and constantly telling me how ridiculous I looked, what a little faggot sissy I was, and making sure that I knew that when we went into the adult store, it would be almost completely up to me to make absolutely clear to whoever was helping us that I wanted to buy the biggest strap on dildo that they had so that my wife could use it to fuck me with.

She told me to repeatedly emphasize that I wanted the biggest one that they had, and to be sure to say that I'd always wanted to be her little housewife, and that as a wife I knew it was only right for me to be fucked by a woman with a strap on dildo, that I'd never been fucked like that before and that I really wanted to have it stuffed up inside my little bottom. She also told me that she wanted to have me take out my lipstick and mascara and touch up my lips and eyelashes several times while I was in the store.

My wife made it clear to me that if my little pee-pee squirted there in the car before we got to the dildo store that she was going to have me spend a full 24 hours sitting completely naked in the corner of the kitchen with no makeup as punishment, so I was very careful to tell her when I was getting close to cumming, and then she'd take her hand away until my pee-pee calmed down a bit.

When we finally got to the store she parked on the street and looked over at me, "Well, sissy -- go ahead and touch up your makeup. I know you want to." And she giggled as I took the lipstick and mascara out of my purse and alternately rolled her eyes and shook her head as I touched up my lips and lashes for her, and then we got out and headed into the store. Usually I followed her everywhere, but this time she told me to go first, and she followed me into the store. I hesitantly pushed open the door and stepped in with my wife close behind me.

There were two people behind the counter, a fairly attractive brunette who looked to be in her early 30s and a younger girl, probably in her early twenties, and they turned towards me as I came in the door, their eyes instantly widening at the sight of me. I knew I must look completely ridiculous with my heavy feminine makeup, my short hair cut and combed like a boy, with the lace of my pink brassiere showing thru my sissy tee shirt, my tiny little pink denim short-shorts showing my smooth shaven nylon clad legs with my pink platformed spiked high heeled pumps and my tee shirt announcing to everyone that I wasn't really a girl, just a sissy who wished he were a girl. I felt like I must be blushing so hard that it would even show thru my makeup.

As they turned to stare at me, I froze there in the doorway, my eyes looking down at my spiked high heeled pumps and smooth shaven nylon covered legs, my tiny little pink short-shorts exposing the curve of my smooth shaven bottom and I was so embarrassed that I could hardly move, but my wife pushed me forward saying "go ON, sweetie. You've been begging me to bring you here for weeks, now go on inside. Don't chicken out now you little sissy faggot."

I moved forward hesitantly, knowing that I had no choice, my spiked high heeled pumps making me take dainty little steps, and she went on. "Go ahead, sweetie. Tell them what you want, and why you want it. Goodness knows you've been begging me and begging me to bring you here for it. Go ahead -- speak up!" And I knew I had no choice.

Addressing the older of the two salesgirls, I spoke, able to look her in the eyes only briefly, then looking down at my feet in embarrassment, seeing my high platformed spiked heeled pumps and my nylons, "ah...do you...um...do you have...um...do you have any...strap on dildoes?" I asked tremulously. She smiled, looking me up and down, and I could see the other girl was also staring at me in amazement. "Yes," she said. "We do carry strap on dildoes." I blinked my mascara covered lashes, my lipstick covered lips parting slightly, but I was speechless.

My wife slapped me hard on my bottom and spoke very firmly, "Go on, you little sissy, tell them what you want, and why you want it."

It was so incredibly humiliating! "I...um...I want...I want to get the biggest one you have...for...for my wife."

My Miss Jennifer interrupted me. "Sweetie, you need to tell her what you really want it for. Don't let her think that you're going to use it on me. You know that's never going to happen, and you don't want her to get the wrong idea. Now tell her."

I blushed again, feeling so embarrassed and humiliated that I could hardly spead. "I...I want to get it...because I've always wanted to be her little housewife, and now that...now that's she's letting me be her wife, I know that I need to...to have her use me as her wife. So...so I need to get a strap on dildo," I glanced over at my wife, "the biggest one you have, for her, so that she can use it on me. So she can, you know, do me with it in my little bottom." There was no way I could look the saleslady in the face as I said that, it was just too embarrassing, so I again looked down at my feet, loving the way my legs looked in my nylons and pink high heeled pumps.

Both of the salesgirls were looking at me in amazement, but only the older one spoke. "So, you want to be her wife, is that right?" I nodded, still staring down at my feet. She looked at my wife and asked her, "And you're letting him, or her, or whatever, pretend to be your wife? Is that right?"

Miss Jennifer nodded. "Sure. He's always been completely useless as a man. I mean, his little thing is so tiny, it's completely useless. He can't possibly satisfy me sexually, so I have other boyfriends, and girlfriends that I enjoy being with." She grinned at me. "And he loves to watch when I get fucked by a real man, don't you sweetie?" I nodded, and answered submissively. "Yes, dear. I love to watch while you have your boyfriends fuck you." She went on, "Tell them what you like to do after I have my cunt filled with a real man's cum, sweetie."

I had no choice, of course. "I...I like to have you sit on my face so that their cum drips down into my mouth, and to have you let me clean all the cum out of your pussy with my tongue."

The salesgirl nodded. "And now you want us to find you the biggest strap on dildo that we have, so that you can find out what it's like to get fucked like you were really a girl, a sweet little virgin about to be fucked like a good little wife, is that right?"

Again I nodded. "Yes, please. Um...could you...could you please show me the biggest one that you have? So she can take me home and use it on me? Please?"

Now both of the salesgirls laughed, and the older one gestured to the younger and said, "go ahead, show him, or her, whatever...where the strap on's are. And then find the strongest dildo harness and show him how to strap it around her waist and put the dildo in it."

And that's what she did. She led me to the left back of the store and picked up a huge black dildo that must have been nearly 10" long and at least 3 inches in diameter and held it up for me. "Does this look like what you want?" I stared at it with my mouth and eyes wide. It was...huge, gigantic! I couldn't possibly take that massive thing up inside my bottom, could I? But I knew I had no choice. "Yes...it...it does." But I couldn't help myself and asked in a trembling voice, "It's...it's so big..." and I blinked my mascara covered lashes, my lipstick covered lips parted. The salesgirl grinned and shrugged. "Hey, sweetie. You said you wanted the biggest one we had, and this is it. We actually don't sell a lot of this one, because it is so big, but..." she giggled, "If you're going to be a good little wife, you have to learn to take it up inside you, don't you? That is what you want, right, to have your wife fuck you like you're the little virgin bride?"

Then she picked up the harness, a wide black leather strap to go around the waist, and two more straps to hold it around the legs, and a hole in front to stick the dildo through, and turned to my wife. "Do you want to have him put it on you now? So that you can be sure he knows how to fasten it on tightly so that when you're fucking him with it, it doesn't slip off or have the dildo fall out?"

My wonderful wife nodded. "Yes, I think that's a great idea." And turned to me. "Go ahead, you little faggot. Get down on those pretty knees and let her show you how to buckle that big fake cock around my waist so that when we get home I can fuck you with it until you cry." It was so embarrassing; I felt completely and totally humiliated, and of course I loved it!

Then I sank to my knees in front of my beautiful wife, and as the young sales girl handed me the dildo and the harness I followed her instructions and slipped the massive dildo through the hole in the harness, then wrapped it around my wife's waist and hips, strapping it into place, so that the gigantic dildo stuck out of the harness like a man's cock, big, hard and massively erect. It was very realistic, with the tip of it shaped like a real penis, and veins running up and down it, and even a pair of big balls as the base. I couldn't help but wish that I could bend forward and begin worshipping it right then and there, kissing it up and down with my lipstick covered lips, then licking and slurping at it until I could take it in my mouth and suck it, and I knew that my wife could see on my face how much I wanted her fake cock in my mouth. But she just grinned down at me and shook her head.

"That's all, sweetie. You can't have it now, so stand up and let's head off for our next stop."

When we left the store, Miss Jennifer had me get in beside her, then drove of in the almost exact opposite direction from where we lived. I knew better than to ask where we were going, and sat there patiently for about twenty minutes until she pulled up in the driveway of a nice suburban house set some forty or fifty feet down a driveway in the midst of a grove of trees. When we came to a stop, she told me to get out and go ring the doorbell at the front door. I gaped at her in surprise.