A Weekend Together Ch. 02

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Fiancee and crossdresser finish their weekend.
2.6k words
4.46
35.1k
11

Part 2 of the 2 part series

Updated 10/31/2022
Created 05/08/2009
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The next day we were awoken by the phone ringing, it was Ben asking us to meet him at a restaurant on the beach at 5. I told him we would be there and couldn't wait to see him again. We got up and stripped down to get in the shower, we took off my boobs and she unlocked my cage saying if I touched it a single time she would put the cage back on and It wouldn't come off for at least a week.

I agreed to the terms and as she took it off it instantly grew to full size. She laughed and said, "you have no idea how hard it is for me to not jump on top of you right this second."

I smiled at this as we climbed in the shower we washed each like we normally do my cock never lost its hardness. When we were done washing we just held each other standing under the stream and kissing passionately just enjoying our time together.

After about an hour we got out, dried off, and went to the bedroom to decide what to wear. We decided on a burgundy tank top and a denim mini skirt for me and she decided on she decided on her white Capri pants and tube top. Before I was allowed to get dressed she replaced the cock cage on me. With that done I put on a black lace bra and matching black g-string and inserted my breast forms into the bra before putting on my skirt and top. Some sandals and a little bit of makeup completed my outfit and we were ready to go.

We got in the car and were on our way, Jessica told me tonight I wasn't aloud to have sex with Ben tonight I would be hers, but a blowjob was ok If I wanted. When we arrived Ben was waiting outside the restaurant for us, he hugged Jessica before grabbing me and kissing me letting his ands slide down to my ass. We went inside and were sat at a booth Ben insisting I sit next to him and with his had on my thigh we ordered and talked as we waited for our food. Ben was 27 and a construction foreman, which explained his build. It turned out he lived in the same neighborhood as us about 4 blocks away, this really appealed to me knowing if I ever wanted a quick fuck it wasn't far away. We ate and had a few drink while our conversation continued his hand never leaving my thigh for too long.

At about seven thirty I had a good buzz from the drinks they were shoving down my throat and Ben asked if we would like to take a moonlit stroll down the beach with him. We both agreed thinking it would be fun. Before we got up to go Jessica placed her hand on bens and looked at him saying "Ben I just want to let you know that I really enjoy your company and ash does as well, but you know I hold the power in this relationship and she doesn't do anything without my approval." He nodded listening and wondering where she was going with this. "I told her earlier tonight she wasn't aloud to have sex with you tonight she is mine. I hope you understand Ben and this doesn't change anything between us."

He smiled and said, "I completely understand that and it doesn't change anything I don't just like ash for her sex. Sitting here getting to know you both I am learning a lot and the more I hear the more I am drawn to you both. So don't ever think me sitting here is going to change just because you want a night with her. She is yours after all."

I just sat listening to them talk and enjoying the kind things Ben said. I had never met such a sweet man, beside myself, who realized there was more then just sex. I sat there thinking that we are going to have to keep him around. As I was sitting there in my thinking I could really fall for this man if I let myself, but I would never leave Jessica no matter how attached I became. All of a sudden I was shocked out of my little world as I felt Ben's hand slide up my thigh to the crotch of my panties and I jumped.

Jessica laughed saying, "Wow ash, are you with us or not?"

I giggled at myself as I told them I was just thinking they both laughed as Ben said, "we probably don't even want to know do we?"

I smiled and said "you would enjoy it and Jessica would be a little shocked but I think she would agree with me on it."

They were both intrigued now and looking at me with puzzled faces. I blushed as I said; "I was thinking how sweet you are and how I could fall in love with you just as easily as I fell in love with Jessica if I allowed myself. But I know I don't want to live without Jessica and she is who I want to marry and spend my life with."

They continued to look at me as they both had a look on their face that they were in deep thought. Ben was the first to respond saying, "well I'm glad you feel that way it makes me feel really good about myself, but I would never try to come between you and Jessica you and her are the perfect halves to a whole."

Jessica came out of her trance and smiled saying, "ash its totally ok to feel that way, before we even got together I knew you were bi and that you were capable of being in love with me and a man at the same time and I wouldn't let you go because you did. I love you just as much as you love me."

With that I smiled as I finished my drink and said lets go walk. We got up and left the restaurant as soon as we were outside I grabbed Jessica around he waist and pulled her to me kissing her passionately she returned the kiss as Ben just stood there and watched. After a minute or two we noticed there was more then just Ben watching so we straightened up and began our walk across the parking lot towards the gulf. As we stopped at the light to cross the street jess turned to Ben saying, "you know ash isn't the only one that feels that way, I'm beginning to fall a little myself."

She looked at me and I nodded my approval, knowing what was on her mind. Seeing that she turned to Ben wrapped her arms around his neck and kissed him as I watched. They were both a little dizzy when they turned back to my smiling face and I wrapped my arms around both of them hugging them tight.

Then the light changed and we walked across the street and the other parking lot as horns honked at us as we passed then walked onto the dark beach. We walked for a while I was in the middle and each of them had one of my hands. When we came to a pretty secluded spot we sat down in the sand and continued talking. As the evening went on, my hand got closer and closer to Ben's beautiful cock. Finally when I was stroking it through his pants and knew he was hard I decided to make my move.

I got on my knees and moved between his legs and undid his pants pulling it out. He looked a little shocked at this as I told him it was ok I have permission to blow him. With that I wrapped my lips around the head of his cock and went to work as I heard him and jess continue talking. I glanced over as I ran my tongue over his cock and saw jess was rubbing herself through her pants then she did something I didn't expect.

The stood up and pulled off her pants leaving nothing covering her but the pink thong panties. She stepped over my putting her pussy inches from Ben's face and pulled her panties to the side for him. I heard the noises as he ate her pussy and her moans as if I wasn't sure what was going on. I began to work overtime on his cock and hearing him moan into her wet pussy I knew he wasn't far off. I wrapped my finger and them around the base of his cock and stroked as I sucked him hard. Within moments his hand was on the back of my head holding it down on his cock as he bucked his hips making me gag, which I really liked. The next thing I knew I felt his cock expand and twitch as he shoot his cum deep in my throat. As I head him moan into Jessica's pussy she started moaning more as she began to cum all over his face.

Once he was finished coming he let go of my head and I licked his cock clean as he continued eating Jessica. I sat back on my heels watching and decided I didn't want to feel left out. So I grabbed the back of her thong and pulled it to the side pushing my face between her ass cheeks and finding her hole with my tongue. As soon as I made contact with my tongue she let out a loud moan and said, "O you dirty like whore lick my ass good while Ben eats my pussy."

That was all the encouragement I needed as I began moving my tongue against her hole then pushing against her entrance. Within moments I felt her shudder and cum again as me and Ben at both her holes, catching each others tongues as we did. She reached down and grabbed us both by the hair pulling us tight against her holes as she had a third and almost collapsed. She released us and we pulled away as I fixed the back of her panties Ben fixed the front. I grabbed her pants and helped them on as Ben held he so she wouldn't fall. As soon as I had her pants done up Ben sat her down so she could catch her breath.

We just sat there looking at her not sure she was ok until finally she said, still out of breath, "wow that was amazing, I have never felt anything like that before."

Me and Ben both smiled telling her she could feel it again anytime she wanted. By now it was getting late and I was still pretty buzzed. Once jess was breathing normal we helped her up and with me and Ben on either side of her we made our way to the car laughing all the way. Once there Ben kissed us both goodnight saying he would call in the next few days that he didn't want to bother us tomorrow we needed a day totally ours. We thanked him again for dinner as we got in the car and jess drove back to the hotel.

As soon as we were in the door jess unzipped my skirt and got down on her knees snatching my panties down as she fumbled with the key around her neck to get my cage unlocked, I didn't complain or try to stop her. As soon as it was off her mouth was around my cock and I was in heaven, then all of a sudden she stopped. She said "o no this isn't totally free for you."

With that she pulled me pink plug out of her purse and squirting some lube on it she pushed it against me as I moaned. As soon as it started to slide in she returned her mouth to my cock and sucked me as she continued to move the plug in and out of me. After just a few minutes of this treatment the depravation of the previous night takes affect and I moan as I loudly as I cum in her mouth. She continues to suck me swallowing all of my cum. She stands up and I am still hard as she kisses me and says, "now that that's out of the way you'll last a while."

We continued to kiss a she pulled me towards the bed. She fell back on the bed on her back and pulls me down on top of her. We continue to kiss as I reached up under her skirt and pulled her panties off her. She grabbed my still rock hard cock and guided it to her hole. When she had it positioned at her entrance she grabbed my ass and pulled me hard against her completely engulfing my cock in her wet hole. She held my ass as I began to pull out of her and she pulled me back in moaning loudly she yelled out "o ash fuck my cunt you whore fuck me good and hard!"

I did as I was told and began pounding her pussy in and out ruthlessly and each thrust she moved her hips up to meet me. I was resting my weight on my arms as she reached between us and pulled off my shirt and then hers. Then wrapping her arms around my back she pulled me down to kiss me, which brought our breast together only covered by my bra. They rubbed together roughly as we continued our fucking. The sensation drove her crazy as she began shaking and bucking even more violently.

After I felt her orgasm 3 or 4 times she looked at me and said she wanted it from behind like a whore. I smiled at this and as I pulled my cock out of her pussy I grabbed her by the hair moving her into position, which made her groan in pleasure. As soon as she was on her hands and knees I pushed my cock back inside her roughly as I continued to hold her hair which made her cry out even louder. With my other hand I smacked her ass 2 or 3 times before leaning forward and roughly grabbing her breast and then finding the nipple and pinch it and twisted a little bit which drove her wild causing her to push back on my cock even harder.

After a few minutes I knew I wasn't going to last much longer I roughly pulled her hair back till her ear was at my mouth and whispered, "your pussy it so tight you little whore I am going to fill it with my cum but only if you beg for it."

With that practically screaming she begged for me to fill her telling me she was a dirty little whore and needed to feel my cum inside her. And as she finished she reached behind me and pushed on the base of the butt plug inside me and that was all it took. I drove my cock deep inside her and let out a loud moan as I exploded deep inside her tight pussy. As soon as my orgasm subsided I collapsed on her back which caused her to collapse on the bed we lay there my cock still deep inside her and I can feel my cum beginning to run out of her as we doze off.

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Omega ManOmega Manalmost 15 years ago
Continuing

Looking forward to additional chapters to this story

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