Lesley and Kerry Ch. 03

Finally, the day arrived. We had about an hour drive to the hotel. We were to meet Ron at six o'clock. We agreed that our excitement level was such that we didn't want to waste time eating and talking beforehand. Ron was to bring the drinks and Kari and I had made the reservations. I spent more time getting Kari ready than I did on my own makeup. I told Kari that it made sense because within the first half hour I would lose all my lipstick and probably the rest of my makeup. I dressed in a sun dress and sandals with no underwear. I dressed Kari in crotchless panties, garters, stockings, satin bra and a nice scoop neck dress. Her makeup was light and tasteful highlighting her feminine assets while camouflaging her masculine aspects. I thought she looked great. She was nervous, of course, not having been out in public. We had practiced quite a lot leading up to our rendezvous. I told her that I wanted this to be the start of our 'lesbian' relationship also. I promised that we would go out in full role reversal just for kicks the very next week.

I knew Kari would be too nervous to go to the lobby and check in, so I did it myself. I went back to our car and got our luggage which didn't consist of much. We packed some shorts and a tee shirt for Kari just in case she wanted to return home as Kerry. When we got to the room, I texted Ron. He answered quickly and said he was just five minutes out. I gave him our room number. I wished we had taken some alcohol for Kari was trembling while waiting for our new bull. I tried to calm her and reminded her of how many times she had eaten me out after sex and how pretty she looked. I had her remove her dress, leaving her in just her lingerie and heels. The pretty pink chastity device shone brightly between the hems of the crotchless panties.

Ron knocked on the door. I was sitting on the bed and motioned for Kari to answer. She was visibly shaking as she reached for the doorknob. Ron was holding a bottle of scotch and looked at Kari. He thanked her and told her how pretty she looked.

"Damn, Baby. If I hadn't met you before, I would swear you were a real lady."

Ron looked at me and nodded. I got off the bed and approached him. I kissed him on the lips and hugged him warmly.

"How about a drink to knock the edge off?" Ron said.

"Fantastic. Kari is very nervous. It is her first time out like this. Too bad about the cage. Her clitty looks beautiful in these panties."

We had a quick drink. I immediately felt so warm and sexy. Kari seemed to settle down quite well. Ron approached me and hugged me again. He felt my ass and quickly ascertained that I wasn't wearing panties. I was already dripping from my pussy. I unbuttoned his shirt and helped him off with it. He was solid and quite muscular. He didn't have any chest hair. I liked that. I unbuckled his belt and unzipped his slacks. I reached inside and caressed a semi hard thick cock. I knew this would be a memorable evening. I stepped back and dropped my sundress. I kicked off my sandals and stood in front of him naked. He finished removing his clothes and unveiled an almost hard cock. It was magnificent. It was almost to its full length and growing in thickness. He was shaved and his black skin glistened. I wanted to suck his cock so bad but I had already established that I wanted to be served orally by both the bull and the cuckold.

I lay back on the bed.

"Kari, Sweet Girl. Why don't you worship Momma's pussy before Ron sticks his big black cock in. Show him whose pussy it really is before we loan it to him tonight."

Kari quickly got between my legs. Her perfume was intoxicating as was mine. She licked slowly up and down my dripping slit. God, I was spewing nectar like a flower. Kari didn't need to get me wet but she did a great job of satisfying me. Not to orgasm. No, not yet. That was Ron's job that evening. I had Kari get up and watch Ron go down on me.

"UMMMM." Ron said between licks, "So wet and sweet tasting. This is some hot white pussy."

"Ohhhhh, god, yes, yes, Ron. I am going to fuck your big black cock. God, you are so big. Kari, he is going to wreck our pussy. I will never be able to feel your little clitty after this. Good thing you suck pussy so well. Now, Ron, lay down on the bed and get ready."

I crawled onto Ron's body straddling his cock with my legs. I moved forward making sure that I didn't brush my pussy over his hard cock.

"Now, Kari, Lover. Take hold of that huge cock and insert him into me. Let him know that you approve him taking our pussy for a little while. See how big he is, Baby. Place him in me and watch how big my pussy gets."

I lined up while Kari slowly took Ron's cock in his hand. I eased back until I felt the tip enter my outer lips. I felt Kari's hand on my pussy also. As I pushed back a little more, I felt the utter fullness of his massive cock. It was not going to be easy; I knew. Kari was still holding Ron as I moved further down his thick member. My pussy was as tight as I could imagine. I had taken big cocks before and I knew I could take Ron's. However, this might be the biggest and thickest I had ever had. When the natural lubrications were coating our adjoining parts, I was able to move back and forth until I had most of him deep inside. I came the first time before we even had a chance to get going. The fullness put so much pressure on my clit that I came immediately. My cunt loosened up more as my orgasm flooded my pussy. I was all the way down on that huge cock when I started cumming again.

"Oh, fuck, yes. God damn, Kari. This is a monster cock invading our pussy. Fuck, it feels so good. I could never do without big cock. Just so you know. He is all the way in my womb. I have never felt so full. OOhhhhh, yes, yes."

I didn't have to worry about Ron plunging into me too hard. He was just lying on the bed. He provided the cock. That is all I needed from him. I was fucking him. I was on top just like I did my husband. I was rocking up and down. My pussy was on fire. I placed my hands on his chest and moved my clit into the most advantageous position. I just loved how I can get the most out of sex by being able to lean forward and bring my clit into my lover's pubic bone. I was screaming so loudly that Kari was afraid that there might be some complaints. I didn't care. This is what we were there for. I was so happy that Kari had selected Ron to be our first black stud. I had already made up my mind that I was going to keep Ron in the stable. I continued to fuck him until I felt his first blast of cum into my uterus. I kept fucking him until he started to soften and move out of me. I fucked him until the last thrust, and he fell out.

When I rolled off him, I looked at Kari. "Okay, Lover. Time for cleaning. Don't waste a drop, Baby. This is one hot load I have deep inside me."

Kari got in bed and placed her hands under my hips. This elevated me so she could access my swampy pussy better. I heard slurping in addition to feeling her painted lips and tongue on my vulva. The sensation of my 'lesbian lover' taking control of my pussy was almost as nice as fucking Ron's big cock. As she licked and sucked his cum, I had another orgasm. I had lost count. There was nothing exactly like having a huge cock all the way in my womb. I hoped Kari was enjoying it as much as I was. To be the center of attention of two people both of whom were interested in making me happy was so special.

Ron and I fucked twice more before we were all satisfied. Well, not Kari. I decided not to take the chastity tube off. I told her I wanted to enjoy her soft feminity. Also, I had promised a special outing the following week. Kerry would have been disappointed at not getting to have sloppy seconds but Kari was satisfied slurping Ron's cum from me after each session. Kari and I slept after Ron left. We already had the hotel. Ron agreed that we should get together again. We both felt comfortable with the way the first outing had gone. I could envision more sessions. There seemed to be an easiness in the way we all interacted. Afterwards, Kari had no reservations about having held Ron's cock. I thought it was a good step. I helped Kari off with her makeup so we could get some sleep. After we showered the following morning, Kerry decided that getting back into costume was not worth the effort as we were just driving home. He put on the shorts and tee shirt and drove us home like a good husband.

I kept watching for signs of regret from Kerry the following week. When he seemed to be happy and normal, I told him it was time for our outing. It was to be low key in a way but still over the top. Thursday after work I went home and got ready. After I showered, I applied a fake mustache. I pulled my hair up under an old ball cap that Kerry wore sometimes. I wore a tight spandex top to try to minimize my breasts. I used a little eyebrow pencil to give impression of a five o'clock shadow. I wore a pair of Kerry's old jeans and a flannel shirt. He had a bulky vest, so I put that on over the flannel shirt. Looking in the mirror, I decided that the bulk on top did indeed hide my rather large boobs. I had removed all my nail polish and dug a little in the flower beds to get dirt under my fingernails. I pulled on an old pair of Kerry's boots which weren't too much larger than my size.

Then the ultimate touch. I had purchased a harness with a medium sized dildo. I used a Velcro elastic band to keep the cock close to my thigh. I didn't want to display a hard-on even though Kerry's jeans were a little baggy in the crotch. I was planning on keeping that a secret until the last.

When Kerry walked in, he knew immediately that this was the outing I had planned. I had picked out his clothing. It was a summer dress of mine that was very conservative. I had a pair of wedge heels which I considered very casual that he could fit into. I laid out his satin bra. I had purchased a special gaff for him. It was tight and aimed to hold his dick in place between his ass cheeks. When he came out of the shower, I sat him down and worked on his makeup. It was very casual and understated but still was attractive. I had styled the blonde wig and it looked great. I painted his toenails and fingernails a soft pink color. I had him step into the gaff panty and tugged his dick back underneath him. This trapped his testicles up into his inguinal canal. The effect was startling. He was as smooth in front as I had been before I installed the fake cock.

She was ready to go, but extremely nervous.

"Honey, you look great." I told her. "We are driving about twenty minutes and going to a nice friendly café. Nothing fancy. Just pop in, eat a quick meal and then we are off again. Remember Ron said he would have made you out for a hot chick if he hadn't already met you and knew that you would be en femme. In fact, as grungy as I am, I would expect guys to hit on you and try to take you away from me. Also, Kari, Leslie still sounds too feminine. Tonight, refer to me as 'Leonard'. Okay, my sexy little chickadee? I am so impressed that I hope I get into your panties tonight before some other stud takes you away."

We hopped in Kerry's SUV. I drove. We made our way over to the restaurant I had selected. It would be a simple meal. Usually, these places were no frills and one could get a good meal rather quickly. Clientele would usually be working people who were not after ambiance but rather good food at a fair price. It was not a typical 'date night' destination. For that reason, I assumed that we would be more under the radar. Not that Kari wouldn't fool 90% of people who glanced casually. If someone suspected the ruse, then so what? We were just a married couple out for an unusual type of date. If it worked out well, I promised Kari that the next date we would go out as girlfriends. I could think of many scenarios that might take care of my needs also.

When we got to the restaurant, we were seated by a hostess who didn't seem to notice anything about us or at least she was good at hiding her expression. She was very young, so I assumed she was more concerned with just seating people. The waitress took our drink order. I had to husky up my voice a little and Kari raised hers a couple of octaves. I thought we did okay. We ordered and got our meals. We tried to role play in our chatting while we were eating. I would ask Kari about her dress and nails and such. She would ask me about how my jeans felt. She didn't know I had my manhood strapped inside his jeans. We took our time eating. I had my cap pulled rather low over my eyes and I was scanning the room for any special interest that onlookers might have if they noticed anything out of the ordinary. We finished and I asked the waitress for the check as all good men would do in the presence of such a pretty lady sitting across the table from me.

She talked with us and bid us farewell. I gave her a very nice tip and we exited. When we were back in the car, I heard Kari breathe a noticeable sigh of relief.

"Oh, Baby. You were great. You looked so hot. No ugly hair anywhere and pretty nails. I'm just glad I didn't have to fight any guys who might be trying to hit on you."

"Very funny, Leonard." Kari quipped.

"How about I take my best girl out for some ice cream on the way home?"

"Really, Leonard?"

"Sure, sugar plum. I'm going to try to seduce you later. I want to pull out all the stops."

She rolled her eyes. I wouldn't stop at a drive thru. I found one of our favorite shops close by and parked the car. Kari got out and seemed to be more at ease. I noticed a little sway in her hips and a practiced short step feminine walk as we went inside. She mulled over the selections and asked for a couple of samples just like any woman would do. I ordered a scoop of rocky road while she settled on the lime sherbet. We ate our ice cream in the shop. We addressed each other by our alternate names and took our time eating.

We had been out for a couple of hours and I wanted to get Kari back home so I could fuck her. After the ice cream shop, I asked her if she was ready to go home. She looked relieved. I managed to pull her dress up so I could fondle her legs and make sure her clitty was still in place. She caressed my hand and let me fondle her feminine charms. I paid careful attention to her breasts. I vowed to order a pair of breastforms to enhance her silhouette. For now, I just grunted as I took advantage of her.

Back at home, I undressed Kari and told her to get ready to take a shower. When she had all her clothes off, I gave her an enema kit and told her how to use it. She was reluctant.

"Bitch." I said in my gruffest Leonard voice. "Do as I say. I am going to fuck you silly tonight."

Surprisingly, Kari did not break the role play. She took the kit and made her way naked into the bathroom.

"And shower after you have prepared yourself."

I had taken the liberty to lay out a baby doll top with no panties. Her ass was going to be mine that night. On the night table I placed a towel, washcloth and a tube of Anal Ease. There would be no doubt what was going to happen once she came out of the shower. I dressed in a wife beater tee shirt and a pair of Kerry's old boxers which he no longer wore.

Kari came out and put on the baby doll. My fake cock was showing outside the leg of the boxers. I had her kneel on the bed while I played with her ass and beautiful clitty. I had her lay on the bed facing me. I wanted to see her pretty face when I invaded her boi pussy. When I pulled the boxers down, she looked at the medium sized dildo. I applied the lubricant to her rosebud and to the cock. I lined up the phallus to her opening and slowly began moving it back and forth until I targeted the cute little hole. When I inserted the tip, she tensed.

"Come on, Baby. You know you want this. You want Leonard to take your anal cherry. Just relax. I will do all the work."

Being her first time, she still was very tense. I would whisper into her ear. I assured her that she was doing good. I pushed the cock a little more past her sphincter while noting that she winced in pain.

"Just a little more, Kari. I promise the pain will turn into pleasure. Just bear with me. You have such a pretty ass. It would be a shame for it to go to waste."

I rubbed her hips as I pushed another inch into her anal cavity. The resistance was not getting any less. As the head of the dildo was inside her now, I began slow moving back and forth. I found that this was the easiest way to penetrate her virgin hole. She began to relax, little by little until my strokes became longer. Just as I was almost all the way in her, she began to moan and shortly began matching my motion. I stopped abruptly and she continued to move her hips. She was fucking me now. I told her what a slut she was.

"I knew you would like this my little bitch. You were made for fucking. Imagine a real cock taking your boi pussy. I wish I could blast cum all the way up you. You are so fucking hot, Girl."

I took her beautiful clitty in my hand and stroked it. She was semi-hard probably due to the initial pain. She managed to get a little more erect as I stroked her. I still had some lubricant on my hands and I rubbed her clitty giving it a sexy sheen. Her scrotum was taunt making her look almost like a eunuch. The pretty white shaft and the dark pink head amazed me as always. Kerry had such a pretty dick. Kari had a such a pretty clitty. As I pulled a little harder on the shaft of her clit, she got almost erect. I was sawing my 'cock' into her ass while she moaned in pleasure. As I pounded her more, she was leaking copious amounts of precum. I love the taste of precum but this time I was busy fucking her bottom. I used the lubricant to slide my fingers up and down the shaft. As she approached her orgasm, the end of the dildo was banging my own clit. I couldn't take anymore and spewed my girl cum just as her clit erupted. Cum was going all over her and I couldn't do anything except tense up more and drive the dildo further up her ass as my orgasm paralyzed me. I was moaning along with Kari.

Eventually her clit began to soften to the tiny wormlike appendage I so loved. I removed the harness and dildo. My clit was still engorged. In fact I was bigger than I ever remembered. This could be that I really didn't notice it when I was fucked by a large cock or even when Kerry ate my pussy and sucked me. Still, I seemed more erect and excited. I went up and licked the cum off Kari's body. I would snowball some back to her when I had an ample supply in my mouth.

"Oh, Baby, Kari. That was the best sex I have had in a while. I can't believe how turned on it made me to fuck your ass. You are the best ever 'girlfriend' and lover. You look so pretty all made up and you dick/clit is so pretty. It is even pretty when it is so soft. And it looks like you don't have any balls. Your sack is so little and tight. I hope you enjoyed this. I want to do this again. Your ass is so tight. And touching your clit while I fuck you is out of this world. Please say we can do this again."

Kari was very demure after the grand ass fucking. She didn't make eye contact with me after we had both cum. I hoped I hadn't gone too far with her. I mean, feminizing her and then fucking her ass. That would give any man quite a lot to think about. I made sure to cater to Kerry for the next few days. I even let him fuck me missionary with him on top, which almost never happened. He was the sub and he was comfortable with that sexually. He loved making me happy in all ways and I also loved making him happy. If he were not a natural submissive, I would never have done all this. As things got back to normal, I brought up the subject about dressing him up again so we could go on a 'girlfriend date'. He again was rather demure but signified that he would love to do this as long as I didn't humiliate him in public.