Shopping Trip

By Richard J. Owensby

Published on Jun 6, 2001

Transgender

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Shopping Trip

Chapter I

I looked over at Rachael, she was sitting down on the couch watching something on television. She was wearing some black skirt and that blasted white blouse I hated. Our daughter was at daycare until 530, we had the whole day to ourselves. I sat by the fireplace pretending to be reading one of my novels, but actually scrutinizing her outfit as she sat there. Really that shirt needs to go, the skirt, eh...it was ok. I tilted my head as I looked more closely at her. She was very pretty, just needed some help picking out some new clothes.

Rachael turned her head toward me, "what?" She raised her eyebrows obviously worried about what I had been thinking. I shrugged my shoulders, "nothing, really." She gave me one more look before turning away again. I laid my book down on the floor and went over to stand before her. She just sat there and looked at me. She started to say something, but she could tell by the look I was giving her that it would be better not to say anything ahelped Rachael a time or two in sucking off some hard cock. As a matter of fact, I know he would love to see me fucked by 2 or more guys. In time that may happen, but right now I have not found anyone but my husband who can turn me on that way. So we settle for finding guys we can meet on late nights and he sucks while I take pictures. Our life is never boring, we have always found ways to avoid that.

"Jamie!" Rachael yelling at me breaks me from the time machine in my mind. I look over at her and smile, "sorry I was spaced out there, I guess." Rachael looked at me and shook here head. "You guess? You were like a million miles away from me there, anything wrong hot stuff?" I smiled at his little sentiment for me. Looking at her straight in the eye, "no everything is great!" I squeezed her hand to reassure her that I was happy and wanted to be doing what we were doing. I know Rachael wanted to know what I had been thinking about, but I didn't want to part with my secret thoughts. My happiness in the life I had found with a wonderful man his wonderful feminine side, Rachael. I laughed to myself, don't want to give her a big ego or anything. "So how much longer," I asked her.

She smiled at me a little nervously, "not far." I smiled and turned towards her, hoping that she could read the excitement in my eyes at our newest adventure. I could see it now us going through store after store going through tons of sexy and beautiful clothes for Rachael to wear. A huge smile came across my face, "Oh Rachael, just think about all the great outfits and lingerie you will be trying on for me today!" I sat back and smiled even more, "maybe even be able to pick up some special treats." I looked over at Rachael who was looking at me like I had lost my mind. "You didn't say anything about trying on clothes." I couldn't help but laugh at the expression on her face. "Well what did you think we were going to do when I said we were going to the mall for some new outfits for you?" I tilted my head at her and waited for an answer. She just shrugged her shoulders at me. "Oh Rachael, dear it will be fun, besides I have more plans than just that for today." Oh boy did I ever I thought to myself. This is going to be a day that will make Rachael blush in remembrance of.

We pulled into the mall parking lot about 10:15 or so. I was already getting really excited and wet at the thought of Rachael trying on some women's clothes in front of other people and especially the men! We walked into the mall side by side, as if best friends would do. I smiled, Rachael was my best friend really, the one woman I could trust with everything. Hoped she trusted me just as much as I trusted her. Smiling at her I pulled her into the mall entranceway. The store was quite crowded for a weekday morning, this just made our trip all that much more exciting to me. We walked once through the mall so everyone could get a good look at my Rachael. I noticed that some people gave us some pretty strange looks, but I also noted that we got some pretty admiring looks too. After the once around the mall we started to go into some stores. The first store we went into was a JCPenny's. I pulled her over to the dress department. I pulled some dresses off the rack, not even really seeing what they looked like, I just wanted her to get in that dressing room and try them on so she could parade before me! After having grabbed at least five dresses we found a women's dressing room. I went up to the salesclerk and told her what we had. She looked at me and looked at Rachael, almost as if she didn't know what to do. "Uh, excuse me, she needs to try these on..." I waited patiently for a response. I know Rachael must be about ready to just leave but I was going to stand my ground. The lady handed over a tag that had five marked on it and pointed to an empty room I gave the dresses to Rachael and told her to go try them on. I shooed her in. "I'll be right out here waiting for you to show me how they look!" I yelled after her. While Rachael was trying on the dresses I looked up and down the aisles for some more outfits for her to try on. After about 20 minutes or so, I looked up I was getting worried she hadn't came out yet. So I walked over and at about just that time she was coming out with the same outfit she had went in on. I looked at her, "Wait a minute, you were in there this whole time and didn't try anything on?" I crossed my arms across my chest. "Uh, well no, I tried them on." Rachael told me simply. I shook my head, now I was the one who couldn't believe what she had just said. I uncrossed my arms and pushed her back in the dressing room, "I need to see how those look, lady, I gave you a direct order and I expect to see how you look in all of those dresses!!!" I know I must have sounded like a bitch to the saleslady, but I didn't care. I looked over at her, "What?" She just turned red and looked the other way. Finally, after about 5 minutes Rachael came out with a blue silk dress that had a slit up the left leg all the way up to her thigh. I looked at her and told her to turn around so I could see how the back of it looked. The back came down all the way down to her ass, showing off a nice back line. I loved the dress on her and made a mental note of it. "Ok, next one." Rachael didn't say a word as she walked back in to try in the second dress I had picked out. Each time she came out and did a little catwalk for me so I could see how she looked in each and every dress. By the fifth dress I could see that Rachael was more comfortable of being out in public now. I looked around me as she went in to put her clothes back on. I couldn't help but notice that a crowd had milled around the room, most of them being men. I smiled to one who I thought was cute. He smiled back at me, I waved at him and he walked over to me. "Hi, miss." He was very cute with those green eyes and his accent sounded so thick and husky that it really got to a girl. "Who is your friend?" I smiled at him as I looked toward the dressing room where Rachael still was. "Rachael, why you like her?" I asked in a cute flirty way. He smiled at me, "well she is cute and you are too..." I smiled and laughed at him, "Oh it is okay, if you find her more attractive than me, I am happily married." He tilted his head at me, "well since you are taken, is she?" I looked at him and just shook my head, "not really." He looked at me confused like so I pulled him aside and whispered to him my and Rachael's situation. He nodded at me and I looked behind me to see that Rachael was watching us, her arms full of the dresses she had already tried on. I smiled at the guy and handed him a piece of paper and left him to go to Rachael. She looked at me confused like as I took all but the blue silk dress from her arms. We paid the lady and left the store. "Okay, Jamie what was that all about?" Rachael asked me. I looked over at her. "What was what all about?" I asked simply avoiding her question. I looked back at her, "we need to go put this dress in the truck." I heard her exasperated sigh behind me, "Why?" I just shook my head and indicated that she should follow. We walked back out to the truck, my insides doing flip-flops as I looked for the dodge and hopefully the man who I had met inside the store. When I spotted the truck, I could see the good-looking stranger leaning up against it. I turned toward Rachael to see if she had seen the man leaning against the truck. By the expression on her face, I came to the assumption that she had. We got to the truck and I told the guy to get in between us. This time I sat at the wheel and told Rachael to get in the passenger side next to the man. I backed out of the mall and went around to the back and parked. Rachael was looking at me, but not more than she was at the man who already had his cock in his hand and stroking it to get it hard and ready for my "slut's" mouth. I could feel myself getting as hot as Rachael must feel. I stopped the truck and got out the video camera I had snuck in the truck the night before. I smiled at the man and then at Rachael, "Well honey, don't be rude--suck this man's cock until he cums." Rachael looked at me with obvious delight on her face. I started videotaping as soon as Rachael bent her head and started to lick that hard cock right there in the parking lot. I paused the camera to lean over and to tell the man to push her down harder onto his cock. I saw his hand on the back of Rachael's head as he forced her down onto the his cock. He bucked up his hips to get even more of his cock into her mouth. By this time Rachael was going like crazy she was deep throating that cock like her life depended on it, she was sucking and licking and teasing that wonderful cock. I noticed her starting to enjoy little by little. When the man was about to cum she stopped her licking and let him settle down before she took him back in her hot mouth again to taste that hard cock in her mouth. By the third time she had done this, I knew she had to be punished for delaying the man's pleasure. So I stepped in and make her give up her position by the man's hard cock, handing her the video camera I told her that her punishment would be to tape it as I finish off our stranger. "Rachael, the man wants to be satisfied not teased." I shook my head at her as I began to stroke the man's cock, "you were being selfish, the true slut in you came out, my little whore, now you have to pay the price." I know she was mad for not getting to taste the mans cum in her mouth but she had to learn not to be so selfish. I started to suck the mans cock and lick it with my tongue. Soon I could feel his hot cum feel my mouth and slide down the back of my throat. After cleaning up the guy, I sat up and re-did my makeup. I looked over at Rachael and told her she should do the same, "You look like a cheap dirty slut with your makeup all screwed up and your hair a mess, fix it." I snapped at her. Turning to the man, I smiled. "Thank you, sir and have a great day." He thanked us and walked off back into the mall. After being sure he was gone I turned toward Rachael. "Have you learned your lesson," I asked her angrily. I walked over to her and kissed her on the mouth letting her taste the little of the cum that was still in my mouth. "You could have had all of that," I told her as I pulled away. Rachael looked at me, "That wasn't nice, Jamie." I looked at her, she was feeling cheated I guess. "You have to learn Rachael." I saw her start to pout, "I wanted that cock to cum in my mouth and you took it all away from me!" I rolled my eyes at her, "Well I guess next time you won't be so selfish with it will you, because if it happens again you will pay an even higher price!" Changing my moods, "now pretty yourself back up we have some more shopping to do." I watched as Rachael re-did her make-up and fixed hair. She still was looking at me like I had done something super horrible to her. "Oh, honey, are you really all that mad at me??" I asked as I smiled sweetly at her. Rachael looked at me and sighed, "No, my love, you were right I was being selfish and deserved the punishment." I smiled at her as we walked back into the mall. Noticing that is was almost noon, we stopped to eat in the food court. We sat and ate our lunch and watched as the people walked by us. I smiled at Rachael, "So you about ready for one more store then we can leave here and go someplace else?" She nodded her head so we threw away our trays and walked on to our next store. I smiled at Rachael as we stood outside a Fredricks of Hollywood. She looked at me and immediately started to shake her head. "You cannot possibly mean for us to go in there do you?" She asked me. I didn't answer, but went ahead and walked into the store. I skipped all of the frilly lingerie and went right back to the leather corsets. I looked at some and glanced around for Rachael, she was still standing outside the store. I stood there with my hands on hips. She finally got the idea and came to look with me. I held up several corsets against her. Finally choosing a black lace up one and a blue button up one, I handed them over to her and told her to go try them on and make it snappy. She did as she was told. This time when she had it on, she called for me to come check it out. She had on the black lace up one, "try the next one, now." I told her and went back out to wait for her to call for me again. I heard her say my name, so I went and looked at her. Rachel stood there with that tight leather button-up corset on, it had pushed her breasts up enough to give her cleavage and sucked in her waist enough to give her very well rounded hips. "Wow! Rach you look hot!" I smiled at her and told her to get changed that that would be great. I made her pay for the purchase while I waited outside. I walked over to the store across the way and waited for her. I turned back to see that Rachael had been stopped by two guys. One of them being the guy we had just had out in the truck. I started to walk over to them, but decided that I should let Rachael handle this one. I sat down on a bench nearby and watched as my Rachael talked to two very handsome men. After about 10 minutes I walked over to where they were standing. "Hello gentlemen." I smiled at them. The guy who I had met at JCPenny's smiled at me, "I was just telling my friend about the great service done to me out in the parking lot." I smiled at his friend and looked at Rachael, "Well would you like to have it again and also have your friend join in back at the truck?" I asked the men. They smiled and nodded. So once more we headed back out to the truck. I looked at Rachael, I could tell she was very happy about being able to suck another cock so soon. I looked at her, "Now Rach don't make the same mistake you made before okay." She nodded at me. We got out to the truck, and all piled into the guys and Rachael sitting in the back. She was sitting in the middle. I started up the truck and pulled out. I started driving around the mall parking lot. "Well Rach, why don't you pull out both of their cocks and start by jerking them off," I said up from the front. I watched as Rachael pulled their hard cocks out of those tight jeans. "That's it baby, stroke them both at the same time," I coached her from the front. I watched and decided that when she had both cocks hard enough I told her to take turns sucking them off. I stopped the truck so I could watch as Rachael took her turns at both of the cocks beside her. Her mouth wrapped around one for a minute or so then she would wrap her painted lips around the other cock, when she wasn't suck one of them her hand was steadily stroking it to keep it hard. Finally she started sucking and stroking harder and faster. In a matter of minutes she had sucked and cleaned up both men. We let them out by their cars. Rachael got in the drivers seat and smiled. "Wow! That was hot," I smiled at her. I looked at her and smiled again. "You are really busy today, babe!"

I noticed that by now it was 230 pm so we headed back to home. On the way there I told Rach to pull in at the truckstop ahead, I needed to make a rest stop. She pulled in, I went ahead and went to the bathroom. As I came back out I could see that there was a group of three truckers looking over at our truck. All liked what they saw I could tell. So I walked over to them and again told them what I had told the guy at the mall. They smiled at me and said that they would love to join us. So with the three guys we walked over to the truck and looked in at Rachael. She had pulled her own cock out and was stroking it. "Aw, little Rachael horny after sucking a couple of cocks?" I asked her. I smiled at the men with me. "Well honey, put yours away you have some more people here who would like to have that mouth on their cocks." Rachael looked at me then at the three men. She eagerly put her cock away and sat up. I looked around the rest area for a convenient place for us to do our little cock party. One of the guys said he had enough room in his cab for all of us. So we all got into the back of his sleeping cab. I put Rachael on her knees in the middle. I then positioned two men in front of her and the one who wanted to fuck her tight little ass in behind her. The two men in front of her pulled out their cocks and started teasing her with them letting her lick only the head of their two cocks, her mouth kissing and sucking each head. The guy behind her was not being so nice, as he pulled out his hard cock he grabbed Rachael by the hips and slowly started to fuck her in the ass, the slowly part only lasted for about a second cause once he got the feel of his cock in that tight ass he pounded her harder and harder pulling her further back onto his cock. The two men in front of Rachael by this time started taking turns by fucking her mouth with their cocks. Each man would pump for a minute or so before pulling out so his friend could shove his cock in her mouth this same routine over and over again. When one started to come so did the other one, making her mouth look like a cum pond. She had cum spilling out of her mouth onto her chin, her tongue trying to catch it all as it squirted out of their cocks. The man behind was still pumping hard and fast into her tight ass enjoying the feel of his cock as it slid in and out of Rachael's ass. Finally with one final thrust he came into Rachael's ass, spent he left his cock inside her ass. After awhile he finally pulled out, the three men all sat down exhausted on the bed and smiled at Rachael and me. "That is one helluva little lady you got there slut." I smiled at them, and Rachael just nodded and sat up to straighten herself out. The truckers said that they all had to get going, but wanted our number so they could give us a call if they were ever back in town again. I smiled and told them that we would gladly have them over. We walked back over to the truck, "Rachael, you are all messed up again." Rachael fixed herself up and by this time it was 400 so we had to hurry to go pick up the little one at daycare. So we headed home. I smiled to myself, we hadn't bought as much clothes as I thought we were, but Rachael had had more than her share of cock I thought.

"So did you have fun on your little trip honey?" I asked her, she looked over at me and smiled. "Yes I did, and I can't wait to get you home to show just how much I did enjoy it." I smiled at her and said, "Why wait," I scooted over and stuck her hard cock in my mouth and sucked her all the way back into town, just as we were entering town she came in my mouth. I held the cum in my mouth and waited for Rachael to kiss me, and when she did I shared her sweet cum with her.

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