Halloween night. I traveled by train to visit with my lover. She’d made all the arrangements for costumes for us to attend a party later that evening. I didn’t know what she chosen or anything about the party itself. I was simply looking forward to the weekend away. As the train pulled into the station I stood at the door, impatiently looking out onto the platform, waiting for the train to come to a complete stop.
I stepped out but I didn’t spot her right away in the crowd. As it dispersed I recognized her large grin on the face of a small man, a police officer. In her bobby costume, complete with hat, she looked like a wee bantam rooster of a cop. Her curves were hidden under the tight, constricting jacket and her hair was hidden under the hat. A billy stick hung at her belt along with handcuffs. She clutched a brown paper bag.
I walked to her and took her into my arms. After we kissed she pushed the bag into my hands.
“We’re running late, ” she said, “slip into the bathroom and put this on.”
I left my knapsack with her and, holding the bag, walked towards the station bathroom.
Before I’d gone two steps she said to my retreating back, “And no underwear allowed.”
Bemused, but smiling, I enter the bathroom and slipped into a stall at the end. I opened the bag and pulled out the first item. A kilt. In just a few moments I’d undressed and donned the outfit. Complete with tasseled shoes, high socks and tam I came out of the stall to see what the effect was. A smiling Scotsman faced me from the mirror. It felt oddly arousing to have no underwear on with the kilt. I felt every breeze caress my legs and buttocks. I stuffed my clothes into the bag and headed out to see Terri.
Her grin was wide as I joined her.
“Come on then, we’re off.”
I followed her to her black beetle and we threw my things into the back. Seated beside her I started to get a sense of how women must feel sometimes as Terri wasn’t shy about running a hand along my thigh. This level of access to hands and eyes felt vastly different from the comparative security of pants. My cock stirred under the kilt.
When we got to the party house, the street was full. We pulled into the village church parking lot. We weren’t the first to do so as the lot was partially full. The party itself passed, as parties do, with interesting conversation, and a spiraling amount of flirting. The kilt got a lot of attention and a number of women were interested in knowing what I was wearing under it. Terri smiled the whole time, enjoying my verbal sparring with the curious. I was standing in front of two, very drunk, women who sat on a small sofa chatting with them. Terri was standing beside me. The redhead, dressed as a witch in a low décolletage black gown, reached out to touch my thigh and looked up into my eyes.
“Can I see?” she asked as she trailed her hand just under the bottom of my tartan.
I felt my cock twitch in response to the situation but before I could answer, Terri slid in behind me and, pressed up against my back, reached around and lifted the front of my kilt above my waist. I was rock hard in an instant and both women on the couch got an eyeful. The bold one who’d touched my thigh leaned forward and wrapped her red nailed hands around my shaft. Her lips were parted and I was sure she was going to take me into her mouth when Terri jerked the kilt back down.
“Enough of that now lad, ” Terri said, “you’re going to come along with me. You can’t go about exposing yourself.” With that Terri pulled the cuffs off her belt and cuffed my hands behind my back. My kilt was tented out, in spite of the weight of my sporran, with the strength of my arousal. “And you Miss, ” Terri continued looking at the redheaded witch, “You’d best come along to file a complaint.”
Smiling, the voluptuous witch stood up. She stood close enough to press her breasts against my chest for a moment while her hand squeezed my cock through the tartan. “Yes, I better had.”
Terri guided me with one hand on my bicep while the witch took the other. We made our way through the crowd and out the front door. We walked through the night and to the church parking lot. To my surprise Terri didn’t go to the car but took us into the church. The witch rubbed up against me every step, too drunk I suppose to worry where we were. The unlocked door led into the chapel. We crept quietly inside, the lights were off and only the street light as filtered through the stained glass windows lit our way.
Moving us to the side of the chapel, Terri set the scene. “Miss it’s pretty late to go all the way to the station house to file a complaint. We could make this felon offer you some form of retribution to make it up to you, if you can think of anything you’d like from him.”
“Oh, yes, ” our cleavage laden redheaded witch breathed, “I can think of several services that could make it up to me. Will you have him do them all?”
“Yes, Miss, it’s only fair after a shock like that. He’ll need to be taught a lesson on top of paying you back, but I’ll take care of that.”
I stayed quiet.
The witch raised the hem of her long black gown up to expose pale thighs with a scattering of freckles. A black thong hid her pubic triangle, but only for a second as she pulled it off and hung it over my head. She lay back on the pew and placed one leg over the back of the seat and the other on the floor to brace herself. She pointed at her neatly trimmed, auburn triangle and said, “Officer, do you think he could clean me up, I got all sticky when he exposed himself to me?”
Roughly, Terri pushed me to my knees, hands still cuffed, and pressed my head to the witch’s cunt. “Yes, Miss, that seems a fair start, ” Terri said. Her voice was husky. I could tell she was getting turned on. I was hard as rock myself.
I could smell the witch’s arousal and her pussy lips gleamed with her secretions. Her hips rose up to meet my tongue before I could get all the way there. She was eager. Her taste was sweetly hot and musky on my tongue. The chapel floor was hard under my knees but I didn’t care as I lapped eagerly, running my tongue from one end of her pink lipped slit to the other. Her clitoris was large and aroused, looking like a miniature cock, so easy to find and I ran my tongue in circles around it, occasionally flicking across it’s hard little shaft. It was so quiet in the church that the witch’s moans echoed softly and the sound of Terri’s trouser zipper was loud.
I couldn’t see what Terri was doing but whatever it was, turned on the witch as she cried out, “Oh yes, do it, do it, do it, ” like a chant murmured back by the echoing walls. She wrapped her hands in my hair, pushing my tam aside and held me tight to her cunt. I felt the kilt come up to expose my ass to the cool chapel air. I couldn’t move my head buy I heard Terri clearly.
“Here’s your lesson boy, Don’t fight me.”
The cold wet sensation that I felt told me lube was being rubbed liberally on my anus. My little ring tightened up but Terri was relentless, working her fingers in and around until I could relax enough for her to slide three fingers in and out. The whole time she worked her fingers she kept up a counterpoint chatter to the redhead’s continuing litany of “do it.”
“I’m going to violate you while this young lady watches. You just continue cleaning her up lad and take your medicine like a good boy. Don’t fight me or it will just go the worse for you. Lick her good and don’t stop, no matter what.”
With that Terri slid out her fingers and positioned something cold and hard against my ring. I pictured the night stick at her belt and I was terrified she’d rip me open with it. I tried to relax as she thrust at me, holding my thighs so I couldn’t move away. One, twice and then she slid inside. So help me, I moaned into the wet pussy of my frantically humping witch. I felt her thighs trembling and licked harder, immersing myself in her totally to offset the feeling of intrusion as a massive presence filled my rear. It hurt, but I didn’t want it to end. At first the thrusts were slow and somewhat painful but as they continued it got easier and then somewhere along the way it turned to pleasure. It may have been when Terri wrapped her little hands around my cock or when the witch had her first massive orgasm driving her cunt against me. I don’t know, I just know that the sensations of submission and pleasure overwhelmed me and I began to thrust back at the cock inside me.
Before I could climax, Terri stopped and had me stand. I finally got a look at what Terri had been using. Sticking out of her pants was a condom wrapped dildo. It was an L-shaped strapless dildo, I was to learn later, held in place by a bulbous end that slides up inside the vagina where it can be gripped. A little saddle in the inside corner of the L, sits over the clitoris. Terri was getting as much pleasure from fucking me as a guy would and had climaxed once already.
At the side of the nave was a high upholstered stool where the choirmaster sat and Terri addressed our witch companion as she nodded toward it. “You’d best go up and sit on that, Miss, and I’ll have this man continue his service to you.”
The flushed witch, seeing the possibilities, hurried onto the stool pulling her hem high over her waist as she sat. Next she pulled the gown off her shoulders and shrugged out of her bra. Her skin seemed to glow whitely in the semi-dark of the church. As Terri guided me forward I saw the scattering of freckles that lay across the white of her full, pendulous breasts. Her nipples had contracted to pink points and she had her legs wide, the inside of her thighs gleaming with her secretions , her feet locked onto the rungs of the high backed stool. Terri pulled off my kilt and sporran leaving me naked from the waist down. My cock bobbed in time to my racing heart. I wanted to bury my cock in the wetness and warmth of the wanton witch before me.
Terri pushed me forward and her small hand, tightly wrapped, around my cock, guiding it into the pink lipped slit, even as the witch reached out for my head and pulled me to her ample breasts. As I knew it would, Terri’s silicone cock pressed against my anal ring even as I slid into the slick warmth of the witch’s cunt. I moved slowly, enjoying the sensation of her parting lips dragging along the length of my cock.
I moved slowly but Terri did not. It seemed the sight of my cock sliding inside another woman, my mouth on another’s breasts was driving her mad. She thrust with all her might burying the cock in my ass with a single motion. She ground it inside me and the dildo, pushed hard against her clitoris. When she pulled back the bulbous end pulled at her vagina, caressing her g-spot. She moaned as she plowed into me and sighed when she pulled back again. In a very few strokes my redheaded receptacle began to thrust back at me, pinning me between the silicone cock and her eager cunt. She kept my head down on her breasts so she could watch every stroke of the silicone shaft as it slid full length inside me and came out gleaming again, covered in lube. She only release my head long enough to reach out to undo Terri’s shirt, freeing her breasts.
The witch began to lose control and convulse, I felt her walls tighten around me and I began to spurt. This was too much for Terri and she pressed her naked breasts against my back while she ground into me, forcing me deeper into the witch. After a moment where we all clung together, Terri pulled me away from the witch and knelt down between her pale thighs. Her small tongue darted between the puffy lower lips, licking up my sperm that dripped out of the warm tunnel. I leaned over Terri to kiss the witch’s luscious breasts once more and to kiss her lips. Her mouth opened under mine and she moaned into mine as Terri found tender spots below. The witch’s hand found my cock and stroked it back into hardness. It seemed only seconds until she was in the throes of another climax as Terri licked mercilessly. Just as the witch started to convulse, Terri stood and pulled the condom off the dildo and slid into the witch with a smooth stroke. I stood back, unable to do much with my hands still cuffed behind me. My cock stood at rigid attention while Terri fucked the witch, their breasts pressed together, their mouths locked onto each other’s. The witch raised her legs and wrapped them around Terri’s small waist and pulled her in tight. I’m not sure who climaxed first but it was amazing to watch.
Terri unlocked me after that, and we all went home together. The night passed with everyone getting turns at everyone else. In the morning we began again, Jordan, for that was the witch’s name brought a whole new dimension to our lovemaking that I can’t forget to this day, and yes, she did take her turn with the dildo, do both Terri and me before she departed.
Via: https://www.lushstories.com/stories/cross-dressing/switching-roles