Naughty Little Shamrock Stories

Over the weekend, my slutty niece Alison came for a visit. Since my husband would be out of town, she brought her boyfriend who she had recently begun to sissify. It was about noon and Friday when the young couple arrived. Alison let herself in, and I met them in the entrance wearing just a short fully sheer pink robe and heels, having just finished my hair and make-up. Alison was a classic goth beauty in a tiny skirt and top that hid nothing. He however was disappointingly in his male clothes. It had been the plan for Alison to forget his bag and bring his girlie clothes instead. In my mostly disapproving voice, “There is no way we can have you walking around dressed like that. Take it off right now.” I said. The boy paused for a minute not sure what to do, but a stern look from my niece forced him into obedience. The shy boy stood there naked, trembling hands cupping his less than satisfying member. “Well come on, let's get you dressed properly” I commanded and led the pair up to my dressing room. 

The boy was in awe at the vast walk-in dressing room and all the clothing it contained. Alison sat him at the vanity under the bright lights and readied the make-up, accessories and a lavender wig she would use. I watched in amazement as she meticulously transformed the young man into an adorable young woman. Dressed in a sexy black bra and panties set with a pair of silicone enhancements to give him the impression of a B cup under a tight short red dress that flared at the skirt. His heels were only 4in, but he walked well enough in them. Then I finished putting on a white mini dress that drew attention to my massive tits and hugged my every curve. Alison would change into a similar purple dress as well. On our way out, we briefly passed my husband. He was just stopping home to get his things ready for the trip with his father and brothers, so we didn't talk long. During that time, he didn't seem to notice it wasn't really a young woman he was checking out. So I put my hand on his crotch and I whispered “Maybe I'll let her suck your dick in exchange for you letting me fuck two more huge cocks sometime” This drew a smile and slight twitch of his little dick.

Our first stop was something to eat. At the restaurant, Alison and I teased and flirted with nearly every male we thought was attractive and each other. Her boyfriend was playfully nervous, but after a couple glasses of wine began to relax and become comfortable in his proper attire. We refused to use his real name or acknowledge he wasn't a woman all night, instead using pet names. Something that would also continue the rest of the weekend. After eating we stopped for a few drinks, her boyfriend loosened up and enjoyed being a girl much more, even gaining the attention of some men. The only thing that gave away the secret was a barely noticeable bulge in the front of the dress that if you didn’t know to look for could be missed easily. We stayed out later than I had originally planned, but it was well worth it. Back at the house, we made our way to the guest room. Alison's boyfriend was quickly sat in a chair and forced to watch me use his girlfriend. It was our typical rough play. I spanked her with my crop, forced her to lick me and used a dildo on her while he watched on his subpar dick staining in panties. As always, her muffled moans managed to escape her gag during her multiple orgasms. After play time, she crawled over to him and sucked his dick before releasing his restraints.

The next day saw Alison and her boyfriend following the rules I gave her last year. Before 730am they were both dressed properly with perfectly done make-up hair and outfits to spend the day by the pool. Alison was in a striped mesh black bikini and thong matched to her traditional goth make-up, I was in a simple pink but micro bikini fitting my bimbo make-up. Her boyfriend wore a bright yellow cut out one-piece, that was sheer when wet. I kept it for when my sister-in-law came over, so it mostly fit. He was far more comfortable than the day before, seemingly even enjoying the sexy swimsuit and heels. All three of us enjoy the water and unusually warm weather. Alison and I played with each other outright, having sex mere feet away from him. All over the pool area we licked, fingered and kissed lustfully. We even toyed with her boyfriend a bit, the tight swimsuit strained to stop his hardening little dick. His skin was soft and smooth, freshly shaved and lotioned. He even kissed like a girl. Occasionally I saw my two playful neighbors Natalie and John watching us but didn't say anything so as not to spook Alison’s boyfriend. I did however make sure to put on a show. At night, we changed out of our swimsuits into some sexy sleepwear. We returned to the guest room where Alison was again strapped to the bed and used roughly by be while her boyfriend was made to watch. My crop found Alison’s pussy ass and tits repeatedly turning then red. Then I made use of her holes with my strap-on until she was exhausted from cumming. I left the room leaving her boyfriend to undo her restraints. 

Sunday saw Alison wearing a micro black and red corset dress that made her tits look huge and let her ass barely peek under the hem with her pure white hair draped over one shoulder. Her boyfriend was surprisingly stunning in a tight short purple skirt and white cropped top. The white top was thin and tight enough to show the purple bra underneath and the straps of its matching thong hung off the feminine boy's hips. Their make-up was exceptionally well done with Alison black eyes and red and black glossy lips.  Her boyfriend’s style matched only, replacing the red with a deep purple the same shade as his skirt. All that with his wig made it easy to forget that it wasn’t a pretty young woman in front of me but her sissy boyfriend. Not to be outdone, but I was in a nearly sheer white mini dress with a pink sheen that hugged every curve from my huge tits to firm ass. Even my pierced nipple clearly displayed under the thin fabric. My dyed blonde hair fell naturally over my shoulders and pink lips glistened.

Our adventure started with some breakfast at a little café. Alison and I were using flirty and teasing selves. After a bit her boyfriend began to enjoy some of the attention the three of us were getting. After eating we walked around stopping at several boutiques I shop at frequently. Saving my favorite one for last. There we were greeted by the store manager, an incredibly sexy short woman with long wavy brown hair. We exchanged quick kisses on the cheek. She has come to not only know but anticipate my style and those I bring to her. I quietly explained the situation with the pretty girl in the lavender wig. With a huge smile on her face she told me not to worry and that she would take care of everything. Here, her boyfriend really came out of his shell. He happily and eagerly tried on each new outfit from skirts, dresses, even lingerie and heels, of course so did Alison and me. A few hours later we were finished, with nearly more bags filled with all kinds of shoes, outfit and accessories than the three of us could carry. We dropped it all off at the car before going out to the bar for some drinks and a little dancing. We drew a lot of attention from both men and other women but mostly kept to ourselves outside accepting a few rounds bought for us.

Back at the house we continued the same as the past nights. Alison was striped to nothing but heels, her wrist and ankles bound to the iron frame of the bed. Her boyfriend sat in his chair unrestrained watching as I placed a ball gag in her mouth. I then used the crop on her still red pussy and tits to get her warmed up. When I was done with the pain portion I undid her wrist and ankles and positioned her on the bed to lick my soaked cunt. Once I had two amazing orgasms. I pulled her up by the hair and bent her over so she could look at her boyfriend. There was no hiding his fully erect little dick in his skirt and panties or the clear stain forming on them. I pulled out my over 9in strap-on making sure to show off it's size to her boyfriend then fucked her tight little pussy hard. Her muffled moans echoed with each of her consecutive orgasms. I used all the force I could until her legs fell from under her. My toy was still when I undid the gag and drove her to several more loud cummings in front of her boyfriend. When she was done I pulled her by the hair making her crawl to her boyfriend. Pushing her head towards the small penis trapped in panties, I grabbed the back of her boyfriend’s head and pushed it towards my strap-on covered in her cum. With only slight hesitation he took the plastic cock between his mouth. Alison sucked on his little dick as I guided him saying “That's it just like she's doing”. He managed to mimic what his girlfriend was doing well enough. “Such a good girl, a good little cocksucker, just like your whore of a girlfriend” I encouraged him. With a lot of guidance and Alison demonstrating on him, he continued sucking to my teases. It sadly did not take long even with her trying to delay it, he filled her mouth. Alison, like the good whore she is, showed him the cum in her mouth, then mounted his lap and gave him a deep passionate kiss. From the look on his face it was clear she passed the load to him. The prolonged kiss forced him to taste and swallow his own cum. Alison and I shared a passionate kiss before I left them alone.

I had left for work before they had to be up and ready but when I checked on them, he was in a pretty nighty full make-up and wig still, and she was naked both asleep. Before they left I received a wonderful photo of the two of them properly dressed, him in a sexy little skirt and top combination and her in a slutty black dress.