The Perfect Anniversary Gift Ch. 05

Each chapter holds a different experience for Caroline and Dave, and each one is a continuation of the previous chapter. I suggest if you have not read Chapters 1-4 that you do so. And for those who particularly like Chapter 2...more like that is coming in chapter 6.

I woke up, alone on the bed, still wearing my strap-on. Smiling I remembered what had happened earlier. Even if I hadn’t remembered the hot sex with Maggie, the tenderness of my nipples and the rawness of my pussy, which had been assaulted by my dildo, were sore reminders. The numbers glowing bright red on my bedside clock seemed to mock my relaxed nature. It was 12 noon and I had an appointment in two hours that would finalize Dave’s anniversary present. I rolled out of bed and walked to the bathroom, my hard cock bouncing up and down with each step. So this is what it is like to wake with a woody flirted through my mind and I chuckled silently. I would have to tell Dave about this…it would definitely confirm his idea that I did indeed suffer from penis envy. This weekend he would see just how much I suffered from it.

I took the strap-on off and cleaned each toy good, noticing that we were almost out of cleaner. I would have to stop by Lover’s Lane and pick some more up…industrial size this time. After peeing I take my second shower of the day. Back in my bedroom I try to find the right outfit to wear, sexy yet business-like. I decide on a red semi-sheer halter top with a deep V-neckline that shows plenty of cleavage, slim tight fitting black skirt with a matching jacket. After applying lotion to my body I put on a red lacy bra and panties, red satin garter belt and black fishnet stockings. I decide on 4-inch black open toed heels. I could at least walk in them and be comfortable, unlike the 5 and 6-inched heel shoes that I have. They were for short-term use only, very sexy but hell on your feet. Big gold hoop earrings, gold choker, a spritz of perfume, run my fingers through my long wavy hair and I’m ready to go.

Coming down the stairs I see Maggie in the living room bent over dusting, her cute butt facing me. She can’t hear me approaching because she is wearing headphones listening to the portable tape player attached to her shorts. I don’t want to startle her so I walk in front of her. Standing up she smiles at me.

"Hi," she says as she removes her headphones.

"Hi Maggie," I say as I walk around the table. " Are you alright with what happened earlier?"

She doesn’t say anything, just nods her head. She looks so sexy standing there that I bend down and let my lips touch hers, they open and my tongue explores the warm inner recesses of her mouth. I feel her melting against me as her arms circle my waist. Her lips taste like sweet cherries and the passion of our kiss is almost too much. She is intoxicating, so young and sensual, yet so naïve and I want to fuck her again. Breaking our kiss but still holding her I tell her that I will call her on Saturday and we will get together and talk, but that I hoped that this wouldn’t be a one-time deal. She told me that she felt the same. I get my purse, pay her, and leave you a note, just in case you get home before I do.

Pulling out of our subdivision I mentally rearrange my day. Oversleeping…unexpected sex (not that I’m complaining I think to myself as I feel my panties dampen) then another nap, has put me behind in my plans for today. I have three stops to make…Lover’s Lane, my 2:00 appointment, and the grocery store. If everything goes like clockwork I could do all of it and still be home before you.

Exiting the highway I pull into the parking lot of Lover’s Lane. It is the closest adult store to us, so we frequent it a lot. The parking lot is almost empty so I get a space near the front door. I know everyone at sometime has gotten the feeling that someone is watching you. Well I felt that as I stepped out of my car. Taking my sunglasses off I see an attractive man staring my way. Whether he was looking at me, I couldn’t tell you, he had on those damn sunglasses that hide a person’s eyes. He was leaning on his car, arms folded in front of him, legs crossed like he was waiting for me. I wondered if he knew me and I just didn’t recognize him. I feel a light breeze tickle my naked thigh and looking down I see that the hem of my skirt is caught on my garter and the tops of my hose are showing. I undo it and smooth the hem down, figuring that is what he had been looking at.

" Nice legs," he said with a touch of mirth in his voice, as I got near him.

"Thanks," I say as I start to walk past him.

"I would love to see what else is hiding under those clothes."

"Keep wishing, because as they say…it will be a cold day in hell before that happens."

"Care to make a wager?"

"I don’t bet with sure losers. Now if you will excuse me I’m in a hurry."

"I would love to photograph you, but with more of these showing," he said as he reached out and touched my breast.

A shiver ran through my body, as I pulled away from him. He grabbed my wrist and pulled me back.

"Let me go, asshole," I tell him as my face burns from the flush of anger.

"I think the lady protests just a little too much. The evidence is also very telling," he said as he pinched my hard nipple through my blouse.

"You are truly a dick," I say as I try to pull away from him. "I’m going to start screaming as loud as I can and have you arrested if you don’t let me go now."

He smiled and let me go. He was an arrogant pig and nothing more.

"I love a woman with sass. Take my card and call me, if you change your mind," he said as he got into his car.

"Not in a million years," I say as I took his card and crumpled it tossing it to the ground.

I was still angry. Who the hell did he think he was? I had one way of finding out I thought as I reached down and picked up the crumpled card. J.J. Reynolds’s Photography Studio was scripted across the top in bold black letters. Underneath it in smaller letters, Family Portraits, Weddings, Pet Portraits, Private sessions, etc. was written. And underneath that in even smaller letters, Private sessions: Individuals or couples, In studio or on location, Very discreet. The address of his studio and his phone number were at the bottom of the card. I started to toss the card back on the ground, but stuck it inside my purse. I just wondered if it was because I didn’t like to liter or did I really want to see this man again. Right now I didn’t have time to think about it. I only have about 30 minutes to get everything I need for our weekend.

Grabbing a shopping basket, I get the lube and cleaner first, industrial size. Then I get some of their bath and body works, as well as some edible chocolate body paint. That should be fun to play with. I spend more time in the dildo and vibrator section. I have wanted a cock that ejaculates and when I see the Peter North one, I decide that it is perfect. It is 8.5 inches long and 2 inches wide. Next I get you a new butt plug, and us a double-headed dildo. You have wanted to try one out, now seems like a great time to do it. Besides I would love to fuck Maggie with it also, one end in her hot pussy and the other in mine as our pussies grinds against each other. Just the sensuous thought of that makes me moan. At the end of the aisle are their new arrivals and one in particular grabs my attention. It is a 12-inch cyberskin dildo that is 7 inches around. My first thought was how I would love seeing you take that in your male cunt…my second thought was how I would love to see Mr. J.J. Reynolds bent over and this buried deep in his ass. I just had to have this one. Maybe I would use it on your tonight.

Checking my watch I see that I only have about 15 minutes to pick out a couple of outfits. Luckily I had already looked in their catalog and knew exactly what I wanted to get. I hoped they had everything in stock and in my size. I head to the latex rack and find the black latex mini-dress that I want. Beside it is a cute purple latex halter and short outfit that I like. I get both and fishnet stockings to match. I pick up some thongs for you in the lingerie section as well as a couple of sexy gowns for me. One is lace and one in satin throwing this in my basket I head to the checkout.

The young man at the register, whose nametag reads, Brad, smiles as he unloads my basket.

"Someone is going to get lucky tonight," he says as he starts ringing up my purchases.

"Tonight is just the beginning. This is an all weekend surprise."

"Must be a special occasion or do you do this every weekend?"

"Special occasion… 6th month anniversary."

He stops and reaches down and handing me a business card.

"Perhaps you would like to have a permanent reminder of your weekend."

I look at the card and see that it is just like the crumpled one in my purse.

"What are you, his promotional agent?" I ask as I lay the card down on the counter.

"Nope I’m his little brother. Do you know him?"

"Let’s say we met in the parking lot and exchanged words.

His smile grew even bigger and a chuckle escapes from his lips. I can see the resemblance now. I wonder if his brother has the same smoky gray eyes. That smile and those eyes are enough to make a woman want to find out what other charms this young hunk has.

"What did my big brother, Jerry do to you?"

"You can ask him, and you can tell him that his actions are not the way to get business."

"He wasn’t very subtle, huh!"

"He was about as subtle as a skunk that has been scared out of his wits," I say as I hand him my credit card.

"That sounds like him," he says as he smiles and bags up my purchases.

I pick them up and hurry out the door. I can hear his laughter mixed in with his wishing me a happy anniversary and fun weekend as the door closes behind me. I toss the bags into the trunk and get my directions to my 2:00 appointment

I pull into the parking lot of a very nice condominium complex with 10 minutes to spare. The address I need is 124-C. Looking for and finally finding a location map I find the C complex. I park in the visitor’s space in front of her condo. I brush my hair and freshen-up my lipstick. I am a little nervous but more than anything I’m excited. This is the special surprise that I have planned for Dave. I ring the doorbell. I can hear it ring inside her condo but nothing else. Maybe it doesn’t work. I wonder what the etiquette is as to how long a person should wait after ringing a doorbell before they do it again and not seem pushy. What would Mrs. Manners say? I decide to ring it again. As I reach to push it, the door opens.

"Hi, you must be Caroline. I’m Taylor, please come in."

I walk into a spacious living room, done in colors of white and blue. I know I’m not doing a good job of hiding my nervousness.

"Hi Taylor, it is nice to meet you, in person."

"Caroline, why don’t you go sit on the couch and I will get us something to drink. A lot of my clients are nervous their first time."

"Taylor, I’m sorry. I am nervous, but I’m also very excited. It is just the fact that I have wanted to do this for a long time and now I’m actually here."

"That’s okay, I understand. Would you like a glass of wine and then we can talk for a few minutes."

"Yes, thank you."

She was a beautiful woman. From her ad on the Internet I knew some things about her. She was 5’9", 135lbs. Her blonde hair was long and wavy and her eyes were green. I also knew that her measurements were 36DD-25-36. Her voice was soft with a kind of hoarse sexiness to it. Some might say she had a smoky texture to her voice. She was very sexy and sensuous. The thing that made her so different is that she is a she-male.

I was checking out some of the paintings on her wall when she came back into the room with a bottle of Merlot and two glasses.

"This is delicious," I said as I took a sip from the glass she handed to me. "I was admiring your paintings. I like modern art. They are very interesting."

"Thank you. I painted them. I have a major in Fine art and art education and taught art at the high school level before I changed careers."

"You are very talented."

"In more ways than one," she said to me smiling seductively at me.

I laugh at her double meaning.

We settle onto the couch with our wine as she tells me about herself. She had tried to fit into society and was a teacher for 10 years. She dated and even had a couple of long term relationships…one with a female and one with a male, before she decided to completely change her life. She started hormone treatments and after 6 months when she started noticing significant changes she quit her job and moved. She started living her life as a woman, and knew that she would never be a teacher again so she decided to find a career where she could have lots of fun and make money at the same time. Taylor told me that she had always been highly sexual, so when she decided to start having surgery she wanted to make herself as attractive and as desirable as she could. After surgery she worked as an escort and loved it. The money was good and the sex was even better. She poured us both another glass of wine and then she reached over and began rubbing my thigh.

"Now, am I what you are looking for. I require a condom for anal or vaginal sex but I do blow jobs and will eat pussy without any type of protection, as long as the person can show me that they are D& D free or if a couple are monogamous. I am tested regularly."

"Taylor you are perfect. As I told you this is our 6th month anniversary and one of Dave’s greatest fantasies is to be with a she-male. I want tomorrow night to be unforgettable for him. We want to share this experience together that is one reason I called you. Your ad said that you do couples. It would be for overnight and it would be at our house."

"I like that idea, as a matter of fact," she said as she slid across the couch and took my wine glass, " how would you like a free sample of what is to come?"

I felt her hand moving up my thigh as she leaned in and brushed my lips with hers. She placed her other hand on my breast and started massaging it.

I stood up and pushed her back against the soft sofa, straddling her lap, my skirt riding up and showing my lacy red panties. I put my hands on her titties and started massaging them as we kissed. Our tongues exploring each other’s wet mouths. Tingles ran through me as I felt her hands slip inside my red panties and grasp my ass. Parting only when we had to breathe she said that we had too many clothes on. I agreed and pulled my halter over my head.

"Oh yes, Taylor," I said as she lifted my tittie out of my bra and licked my hard nipple.

My panties were getting wet and I could feel her getting hard beneath me. She reached behind me and undid my bra. Now she had complete access to my titties. Cupping my breast she licked, sucked, pinched, twisted, and pulled on my nipples. She licked circles around and massaged both of my mounds. I was rocking back and forth on her hard cock; my skirt pushed up around my waist. She moved her hand between my thighs and rubbed my wet pussy pushing the material into my slit. I slid my hand under her top caressing her breast.

"Oh fuck Taylor that feels so good," I said as she slipped her hand into my panties and her fingers found my hard clit.

"How do you like it, Caroline? Do you like it soft and gentle, or a little rough? Do you like it nasty and dirty?" Do you want to be my bitch or my sweet sensual lover?" she asked as she bit down on my nipple and pinched my clit causing me to squirm against the palm of her hand.

I was amazed at how well she could read me.

"Ohhhh Taylor, rough, I need you to fuck me hard and fast."

She pinched my clit and pulled and twisted on my nipple again. She pushed me back against the couch and was sliding my panties down. I was busy unbuttoning her blouse. When I had it undone she pulled it off and then took her bra off. I reached up and caressed her sexy titties. They were beautiful. She leaned forward and I took a nipple into my mouth teasing it with my tongue, before sucking on it like a hungry baby. Her hand was busy between my open thighs. I moved from one tit to the other savoring the softness of her mounds and the delicious hardness of her nipples. Her hand was torturing me.

"I’ve got something else you can suck on, Caroline," she said as she pulled back and stood up. Taking my hand she pulled me off the couch and led me up her stairs. As we entered her bedroom she pulled me to her. Oh the erotic feel of her titties mashing against mine as her tongue entered my mouth. I could feel my juices running down my thighs. I reached down and rubbed her cock. I wanted to see it…to touch it, to taste it. I slid down onto my knees. Undoing her skirt I let it slide down her legs; she delicately kicked it away. I could see the outline of her hard cock through her satin panties. I rubbed my face against it, feeling a wet spot where her cock had leaked. I licked that spot with my tongue, getting my first taste of her. She pushed me back and slid her panties off. Her cock sprang out and slapped me in the face before I could grab it with my hands and bring it to my mouth. I looked up at her as I grabbed her cock and licked the head. She was playing with her titties. Holding her cock and watching her play with her titties almost made me cum. I licked up and down the shaft as I massaged her balls, which were big, not small like some of the she-males I had seen in pictures. I let my tongue trail over the head and slip into her slit…dragging her precum out. I couldn’t wait anymore.

I slipped my lips over the head of her thick 9inch cock, licking all around it. I could hear her moaning as I let more of her cock slip into my mouth. Looking up at her and seeing her titties and knowing that I was sucking her cock…was too much. My already overheated pussy exploded causing me to moan against her cock. She was pushing my head down on her now, her hips seesawing her cock in and out of my mouth…harder and faster than before. I could feel her cock swelling in my mouth as her balls slapped against my chin I was ready to take her cum…I wanted to taste her. Suddenly she withdrew her cock from my mouth. She pulled me up and kissed me, our titties mashing together again.

"I want to fuck you and cum in your sexy cunt," she said finally. "Do you want that?"

"Oh yessssss," I moaned.

"Get on the bed, and grab the headboard," she said as she reached onto the dresser and got a condom.

I watched her unroll it onto her big cock. I couldn’t wait to feel that cock in my wet pussy. I needed to be fucked and this sexy she-male was going to fuck me. I did as she asked spreading my legs as far apart as I could. The mattress gave with her weight…I could smell her and feel her breath before she ever touched me. Chills of delight raced through my body.

She kissed my back and up to my neck, her hands coming around to grasp my breast. I felt her cock trapped between us as she pressed her titties into my back. She slid one hand down my stomach and started rubbing my clit. No words, just moans and erratic breathes could be heard. I was fucking her hand…trying to get her fingers inside me. I needed to be filled. I needed to be fucked.

"Oh God, Taylor, fuck me please. Fuck me, nowwwww," I begged her.

"Patience my little slut, I’m going to fuck you, but I want you to cum first."

She pushed two of her fingers inside me. I gasped as she searched and found my G-spot.

"Ohhhhhhh fuck Taylor….yesssss fuck my pussy."

"That’s right, Caroline, my little bitch, cum for me," she said her voice calm, with an edge to it.

For some reason this excited me more. She was controlling me…and I loved it.

"Cum for me, my little whore. Tell me Caroline, are you a whore?"