I woke up slightly before dawn and felt refreshed and rested. I immediately thought today was day four of my adventure fantasy. It was also the last day we had planned. I would be staying one additional day and then headed back to the airport on day six. I was excited to learn what was in store for me and also a little nervous. My ass was still aching and sore and I could see my entire bottom was a crimson color of red from the last spanking I had received. The towel was covered in cum that had leaked from me overnight and I was still leaking slightly. I again used an enema and that seemed to work. I took a shower and applied my lotion noticing my cock cage. I could not believe I had been up for an hour and not thought of it.
Jim came into my room after knocking and announced “Tammy, it is time to get ready. We have several errands to run today.” I was surprised he was still referring to me as Tammy but answered from the bathroom and asked what I should put on as my bag of clothing was not in my room. Jim replied to wear whatever I wanted in my dresser or closet and he left the room saying Pierre would be in shortly to help if I needed anything.
Everything in the dresser and closet were ladies clothing items and undergarments. I could not be seen in public dressed like this I thought. Pierre came in and I told him my concern and he just replied that I was such a silly girl, I looked beautiful and said he would help pick out something sexy for me. He ended up dressing me in a pair of very skimpy lacy panties, a bra that was filled and then a pair of thigh highs, a short mini flowery colored skirt and a small top that showed my midriff and at least to me really accentuated my breasts. Pierre applied some light make up and another splash of perfume and did put a wig on me that looked very natural. As he stood behind me in the full length mirror I could not but help thinking I did look attractive as a woman and maybe this outfit would work when I met Robert. As the thought ran through my mind I quickly returned to reality thinking I could never do anything like that and we were off.
Pierre told me that my skirt was very short and if I did not bend over correctly I would show everyone my pretty lacy panties and probably attract attention. Jim added in that when we sat I needed to sit like a proper lady or my cock cage would show. I could not believe I was actually going out in public dressed like this. It was humiliating and invigorating at the same time and I wondered in my mind if the guys would really go through with this or would simply return home. My answer came a moment later when we pulled into a large shopping mall packed with cars and Jim parked.
We walked into the mall and went through several stores as Jim and Pierre shopped and picked a few things up along the way. At one point I was in a Bed Bath and Beyond and had bent over to pick something up on a bottom shelf and felt a hand on my panty covered ass. I quickly got up and turned to see a younger guy probably in his twenties smiling at me. I blushed and he remarked that I had a hot ass and he would like to see more. I just smiled at him and caught up with Jim and Pierre. I wondered if he really thought I was a lady or if he knew I was really a man. I could see the guy was following me and tried my best to keep my skirt down. I finally thought he had parted off and I went in to use the ladies room. Inside I was scared to death of being caught and sat on a toilet in one of the stalls and peed through my cage. I wiped and dried it off and then washed my hands and left. The guy from earlier was standing in the hall and pressed up against me and told me he could show me things the two old guys could never do for me. He ran his hand up the back of my skirt and rubbed my ass as I was afraid to speak. As his hand reached inside my panties and he started to dip to the lower part of my crack saying he knew my pussy had to be wet Jim stepped around the corner and interrupted him. His fingers had to be a mere hairs length from my balls and I instantly stepped back and Jim let into him about messing with his wife. The guy could not get out of there fast enough and took off and we left.
We were in the mall for several more hours and I was extremely aware of how I as standing and what position I was in at all times. It may have all been in my mind but the rest of the day I felt like I was being watched by everyone who saw me. Before we left we walked into a lingerie shop and Pierre found a salesman. Pierre told the guy who had to be gay that I was their girlfriend and they were looking for some really hot slutty panties for me to help turn them on. This guy in the store had to be the most helpful clerk ever and went out of his way to find things for us. He asked me what I liked and what I was looking for. He asked what I was into sexually and what I liked, what made me feel sexy. I was dying inside and wanted to crawl out of there but answered the best I could and left with a bag of dainty little things in just my size.
Finally, we left the mall and I thought we were headed home when we stopped at a restaurant. The place was full and we were seated at a table with Jim and I on one side and Pierre on the other. Pierre was holding my hands and Jim was kissing me and running his hands over my body getting a feel. I knew every eye in the place had to be on us and I felt like everyone there was probably thinking what a slut I was. Jim pushed me to the floor beneath the table after whispering to me that it was time for desert and they both had something for me under the table cloth. I was so embarrassed thinking everyone was probably looking and saw me go under the table. I just knew everyone could see me under there. I moved to Jim’s lap and he already had his belt unfastened and I unzipped him and pulled his cock out. He was already fully erect and I went down on him trying to be as quiet as I could. As I sucked Jim I reached over and Pierre already had his cock out of his pants and I grabbed him with my free hand and did my best to give him a hand job. I took Jim about ten minutes and he pulled my head into his groin and I felt his hot cum hit the back of my mouth. I did my best to get every drop but felt some leak down my chin and cheek. I sucked him until he pushed my head away and was immediately grabbed by Pierre who I had totally forgot about and I took his cock into my mouth. I guess watching Jim orgasm at the table must have had Pierre on edge as he was already leaking precum and it did not take him long before he was adding his load to my mouth. I sat beneath the table for a few minutes until our waitress left leaving the check and Jim pulled me up to the seat. I just knew everyone in the place knew what I had just done. Jim told me to leave the cum on my face and he paid the check and I walked out with Jim holding me on one side and Pierre on the other getting looks from several of the other patrons and employees.
Pierre told me I looked so hot and slutty with the cum on my face and to leave it there. I don’t know how noticeable it was but I did now if someone was looking they could tell what it was. I sat in the car next to Pierre feeling like a total slut as we drove.
We pulled into a bowling alley and went inside. Jim said he loved to bowl and wanted to play a few games before heading home. Jim brought me several drinks and we played a few games. I am not a bowler and was getting more gutter balls than anything. Jim and Pierre were actually pretty good. They along with the rest of the all-male crowd were all really enjoying watching me on the ally and my panties coming into view each time I threw the ball and my skirt naturally raised. The comments were all getting Jim and Pierre really excited and on several occasions when a guy was commenting on my ass they told the guy he could come over and touch it. He rubbed his hands all over my ass squeezing my cheeks making me blush before Pierre told him that was enough and the guy moved back to his lane to brag to his buddies. As I had a few drinks I began to relax more and was putting on a show as I threw my ball each time allowing my skirt to rise. I was really enjoying the comments and attention and could feel my cock was straining against my confining cage. As the night continued bets started to be made that if a guy could pick up some hard to hit spares that I would show him my ass and I would stand and pull my panties down over my cheeks and I even gave a few hand jobs when told to by Jim or Pierre. After several games and the guys wanting to touch, feel and see of me Jim decided it was time to go. I sat in the back seat feeling very good and impressed with what I had done that day. The cum on my cheek and chin had not gone un-noticed by several of the guys at the bowling alley and I quickly had the reputation of being a cock slut. I was amazed that I was able to turn on a whole group of testosterone fueled guys and have them all wanting me. I was beginning to enjoy and like being Tammy and felt like I had found my inner slut. As we drove home my mind wandered at how I was going to adjust going back home to being in a business suit 16 hours a day and being in total control acting totally straight was going to happen.
Back at the house I was taken back out to the out building and spanked for getting so many men’s dicks hard. The spanking felt good as I stood bent over at the waist with my skirt and panties pulled down to my knees. My wrists were restrained to a bar with my ankles the bar continued to be expanded spreading me wider and wider. Once my spanking was completed I was once again locked inside the cell I was in the first night and left there. Unlike the first night I fell to sleep quickly feeling very content and my feeling of nervousness being gone. My ass stung from the spanking and I knew it was a bright red. I fell asleep in my bra and panties until I was waken the next morning.
On the morning of day five both Jim and Pierre came in and woke me up. I left the cell and as we walked outside my eyes adjusted to the sun. It was a beautiful day and the sun felt good on my exposed skin. I stood as Jim took the key from around his neck and undid my cage and freed my cock which instantly sprang to full erection. Jim got on his knees and I felt Pierre come up behind me and pull my lace panties off my hips as Jim took my swollen and sore cock into his warm wet mouth. Pierre parted my cheeks and started to rim my ass and I told them both I was going to cum and exploded with Jim taking every drop into his mouth. My orgasm felt like it lasted for ten minutes as jet after jet of cum worked it way from my balls and out my cock. I felt my legs begin to shake and get wobbly from the intensity of my climax and Jim eased me back onto a chair before I went down. Pierre pushed my legs back up over my shoulders and continued to rim my ass and I could feel my cock growing again.
Jim remarked that I had to just blow the largest load of cum ever and I told him with my voice shaking that the lack of orgasm and being turned on for four full days was torture but the release almost brought me to loose consciousness from the intensity. As I lay back starting to regain my strength Pierre continued his oral magic on my ass and was jacking me off with me being back at full hardness and arousal. I closed my eyes and began to moan from the feeling and after about ten minutes felt jet after jet of my hot cum splash over my face and chest in another incredible mind blowing orgasm. This time I kept my eyes closed as I felt Pierre move away and I feel off to sleep on the chair.
I woke up several hours later still in the same position and Jim and Pierre were sitting watching TV near the bar. I gave them both a kiss and thanked them for such a wonderful week and incredible new experiences. I then told them that I had had the most incredible orgasm I can remember and kissed them both again. I went into the private bedroom and showered, shaved and put on lotion again. My clothes and bag were on the bed and I dressed back into my boxers and jeans and then looked into the mirror. I slowly undressed and stood looking in the mirror naked once again. I pulled out a pair of very intimate delicate pink panties and pulled them up over my hips. I liked the way they looked and felt. I dug and found a pair of pink thigh highs and pulled them onto my freshly shaved and smooth legs. I found a short cami swing top that covered my chest but left my stomach on display and looked into the mirror. I put on a dab of the perfume and put the heels back on and then walked back outside sitting with Jim and Pierre along with two of their friends, Ted and Bryon. I walked up and sat between the two guys on the couch facing Pierre.
Ted looked up and nodded his approval saying “Damn, you didn’t tell us you had company over. Are you going to introduce us to this gorgeous sexy lady? Or are you keeping her all to yourself?” Ted moved closer to me and touched my leg introducing himself as Bryon spoke up “Damn, you guys tell everyone your gay and your hiding something like this?” Jim spoke up and said “This is Tammy, she is visiting us to enjoy the pool and sunny California. Tammy, this is Ted and Bryon two of our straight friends who just stopped by for a drink.” Bryon moved closer to the other side of me and began rubbing my other leg. I was surprised that my lack of breasts and my soft cock in the front of my panties had not given me away and was a little nervous at what reaction they may have when they noticed. I was deeply enjoying the attention and show as both guys did their best to impress me with their pickup lines and compliments. Ted had pushed my stocking down my thigh and was rubbing my leg telling me I had the smoothest softest skin he had every felt. I got up and grab a drink with lots of comments about my ass. The tight pink lacy thong did not hide much apparently both guys likes the view it offered. I stopped for a moment and shook my ass at them both and then walked back over to sit between the guys. Byron asked if he could see my ass one more time and I turned and stuck it out at them feeling Bryon’s hands grab my cheeks and pull them apart before I could sit. I was surprised when I sat before I could get my drink to my mouth Ted moved in and gave me a big wet open mouth kiss as Bryon rubbed my bare exposed leg and kissed my neck. I felt Byron’s hand moving up my leg and quickly put my hand over my crotch before his hand tried to get a feel. I parted with Ted and got up and said I needed to go inside but it was nice to meet them both. I got a slap on the ass from one of them as I walked off breathing a sigh of relief of having been found out.
I walked inside with my cock hard from the attention and pushing out of my delicate panties but I did not touch it. I grabbed my phone and called Robert as I lay on the bed. He answered and we were flirting and talking. He asked if I wanted to join him at the resort and I told him I could not wait. I was lying on my stomach facing the headboard when I heard a sound behind me and felt a large pair of hands on my hips. I felt my panties pull off my hips and then felt hot breath and the whiskers of a man’s face bury between my cheeks as I was spread open and a tongue pushed into my now exposed bottom. It felt great but I was not sure who was there and struggled to move away. It was Byron and he was telling me I had the hottest ass he had ever seen and he wanted to spend the night licking my ass and pussy and fucking me deeply. I grabbed the blanket to keep my rock hard cock hidden and jumped up telling Robert I needed to go and putting down the phone. Byron continued telling me I smelled amazing and how much he wanted me as I pushed him to the door closing and locking it behind him. He tried to talk to me through the door but finally left.
It was about an hour before I heard Jim and Pierre come into the house calling my name. My mind had been racing with thoughts of feeling Bryon’s hot breath, his forceful control and his tongue push inside me. I was turned on and nervous at the same time. His tongue had brushed the base of my scrotum surely he had to know I was a man but did he? Pierre asked why I was in the room alone with the door locked and I told him about Bryon, Both Jim and Pierre apologized and said they did not know he had come into the house. They both laughed saying I had driven both Ted and Bryon crazy with lust and that they could never find out because it would burst their pride. They said if Byron only knew he had licked another man’s ass and nearly licked his balls he would go insane.
The rest of the day I remained in my panties and outfit and we sat around the pool talking about everything that had happened over the last four days. We enjoyed several drinks and it was a wonderful day. That evening we sat around still talking as I shared my feelings. We agreed to do this again and to remain in contact and decided to head to bed around 12:30 as I had a flight out the next morning at 11. I slept nestled between both Pierre and Jim. The guys stripped me out of my panties and clothes and both took turns fucking me slow and hard before each filled me with one last load of their hot cum. I think I reached orgasm at least four times from the oral stimulation At one time Jim was deep inside me filling me completely as I was kneeling over Pierre in a 69 positon with Jim inside me from behind. The pressure on my prostate was overcoming as I flooded Pierre’s mouth beneath me. Once we were done I slept like a baby until early the next morning.
After showering and dressing back in my regular clothing we set out for the airport and I was dropped off at the terminal. I talked to Robert while waiting for my flight and we planned our trip for just under a month. We would meet on a Thursday evening and then fly back out on Monday morning. I was already excited.
Once back home I stopped and dressed in my business suit and was ready to head into the office where I would once again be incomplete full control and could never show this side of me. Before I left I unpacked the bag of dainty delicate panties into a drawer and smiled.