I want to thank the readers for hanging in there with this story line. I also want to thank you for the wonderful comments. I appreciate you all for taking the time to send me an email or comment, I will respond to you all.









Chris and Jessica had to leave for a dinner engagement which they could not get out of. Emily and I we wanted to be alone anyway so we were glad.



Jessica and Chris weren't even out of the driveway before I slipped behind Emily, reached my arms around her chest tweaking her nipples, and then I started rubbing my cockhead between her cheeks. "MMMMM! That feels nice. I'm going to clean the kitchen up a bit. You grab the towels outside and put them in the laundry. I will meet you in the bedroom in five minutes."



I ran out the backdoor to grab the towels, tossed them into the laundry room, and skipped down the hall to our room. I put on the red baby doll top, threw myself onto the bed, and struck a pose as I slowly jacked my hard cock. I heard Emily coming down the hall. I felt my mouth drop open as she stood in the doorway wearing Jessica's eight inch strapon.



Emily grabbed her cock and waved it at me, "You said anything did you mean it?"



I spread my legs and held open my arms, "Oh god yes. Please fuck me baby. Fuck my boy pussy."



Emily moved to the edge of the bed and offered me her cock, "Suck it. Get me ready to fuck you."



Emily grabbed me by the back of the head and guided me towards her cock. I grabbed hold of it and rubbed it across my lips. I looked up at her as I ran my tongue all around the head. "Oh ya baby, that's it show me how much you want my cock. That is so fucking hot. You're going to make me cum watching you suck my cock." Emily held my head and slowly started to face fuck me.



I was taking in about half of her cock, "MMMM, ya that's it cocksucker. Take it deep. Get me ready to fuck you. You want this cock baby? You want me to fuck you with this cock?"



I was now on all fours getting face fucked by Emily who was standing on the side of the bed. Her dirty talk was driving me mad. She has never been so aggressive. I nodded my head and wiggled my ass for her.



Emily shoved me away as she walked around the bed, her cock dangling in front of her dripping with my spit, "Stay like that and don't move." She ordered.



The bed rocked as she got onto the bed behind me. I felt her cold finger on my ass as she applied lubricant to my hole. She shoved her finger deep into my hole and went right for my prostate. If you've never been fingered before by a doctor then you haven't lived. I moaned, "MMMMM, yes."



"Is this what you want baby? You like having your ass played with?" She said as she applied more pressure on my prostate.



I was panting and almost out of breath as she continued to work my opening, "Yes please yes. Fuck me, take your big cock and fuck my pussy. I want to be your little slut. Put your cock in me please." I was begging and pleading to get fucked. I wanted it so badly.



Emily pulled her finger out of my ass and I felt her big cockhead pressing against my hole. Emily slapped my ass, "Turn over bitch I want to watch your face as I fuck you."



I flipped over onto my back and raised my legs in the air. Emily grabbed my ankles and scooted her cock closer to my hole. She placed her cockhead against my puckered hole and looked down at me. The lust in her eyes almost made me cum. Emily applied a little pressure to my hole. I pushed out and relaxed my muscles as best I could. "Is this what you want slut? You want me to fuck you like the slut you are? Tell me you want my cock."



I was a whimpering pussy now. The level of my desire was off the charts. I was rotating my ass against her cockhead and purring like a slut, "Yes fuck me. I want to feel your cock inside me. I want you to fuck the cum right out of me. Fuck me hard. Stretch my pussy and fill me with your cock."



I felt her grip tighten on my hips and knew she was going to push. My ass stretched but didn't give way completely. The pain shot through me and I shoved my ass against her cock. I didn't want to scream out and scare her or break this moment of lust. She pushed a bit harder and the cockhead passed my sphincter muscle. My body relaxed "MMMMM, YES."



Emily pulled back just enough where I felt her cockhead pulling out, before she pushed back into me filling me with half her dick. "Oh ya, take my cock slut. Oh James I'm fucking you. This is so fucking hot to watch this. I never knew this would be so fucking hot. Your ass is opening up and taking my big cock. Does it feel good baby? Is this what you like? I want to fuck you all the time. I want to fuck your tight ass."



"Yes M, fuck me. Shove that cock inside me. Give me all of it." I felt the sweat dripping off my forehead. The pain was gone. My ass was fully accepting the girth of her cock. The cockhead was now massaging my insides.



Emily started to fuck me harder and deeper. I held onto my calves, helping to keep my legs spread. Emily leaned into me as she bottomed out her cock and I felt the fake rubber balls pressing against my ass. She slowly ground her cock deep inside me, "Oh fuck I can't believe you took this big monster. You like my cock deep inside you don't you? I am going to cum just seeing you like this."



"I love you Emily. You can fuck me anytime." I reached my head up and we kissed.



Emily moaned in my mouth as she started an orgasm. She rose up, wrapped her arms around my thighs, lifted my ass off the bed, and started to fuck me long and hard, "Oh god I'm cumming. I am going to fuck you hard. OH yes, mmmmmm. You like this James? You like being fucked by a cock? Do you wish it were Chris fucking you? Ya I want to see that. I want to see Chris standing over you with his strong muscular body and his big cock fucking you like the slut you are. OOOOOHHH YYEESSSSS! Fuck him baby. Let him fill you with his cum. Chris is fucking you oh yes feel his cock inside you. AARRRGGG!" Emily was dripping sweat all over me as she fantasized me being fucked by Chris. She came hard.



The image was too much for me. I screamed out as my cock spurt cum all over my chest without either one of us touching it. "Oh Chris fuck me. Fuck me with your big cock. Fill me with your cum. AAAHHHH!"



My legs were cramping as Emily lowered them down. She kept her cock deep in my ass. Her body fell onto my chest as my cum spread between us. Emily reached up and rubbed my face, "That was hot." We both fell asleep in each other's arms.



I woke when I felt Emily's cock slip out of my ass. I kissed the top of Emily's head and rolled off the bed. I hurried to the bathroom to clean myself up. Emily must have heard the shower as she walked in still wearing her cock. I grabbed the soap and washed the giant phallus, still amazed that it fit inside me. I unstrapped the harness, reached out the walk in shower, and placed it on the sink counter. I returned so that we could finish our shower.



I put soap on my hands and embraced Emily. I soaped her back and ass. I used a soapy finger to glide along her ass crack. This brought out a moan of acceptance, "MMMMM, I see why you like that so much."



I turned her around and braced her against the shower wall. I used my soapy finger to gently penetrate her. I used the rest of my body to pin her against the wall. I reached my left hand around her front and across her chest until I found her right nipple. As I pressed my right finger deep into her ass I pulled on her nipple and pressed my body against hers. "Oh yes James, yes. Fuck me baby. I want to feel your cock inside my ass. I want to feel what you feel. Fuck me."



I pulled my finger from her ass and replaced it with the head of my cock. I was hoping the soap would be enough lubricant as I pushed my cockhead into her. "UUUHHHH! Yes that's it almost inside." She moaned.



I pulled back and let her ass work my cockhead until I felt it open up. When the pressure subsided I pushed my cock into her. "Fuck yes, that's it. Oh man that feels so good. Mmmppphhhh!"



I again pushed her up against the wall as I pressed my cock further into her. I was now able to grab both of her nipples and pull on them as I began a nice rocking rhythm slicing my cock in and out of her ass. "Feels good doesn't it M. Feel my cock buried in your ass. MMMMM" I kissed the back of her neck.



Emily was moaning and rotating her hips against my cock, "Oh yes fuck me. Oh mmmmmmmm!"



Emily's head fell back against me as I continued my seduction, "Wouldn't you like to feel Chris' cock being pushed deep inside your ass? Feel my cock inside your pussy. Being sandwiched between Chris' body and mine? Feel his cock M. Feel it moving inside you, pumping against your body. His hard nipples scrapping against your back. His strong arms wrapped around you squeezing your nipples."



I pulled Emily's nipples really hard and gave them a twist as I shoved my cock deep inside her ass. Emily pushed back against my cock and froze as she had a violent orgasm, "OOOHHH, yes Chris fuck me hard baby. Feed me your cum. UUGGHH!"



I shot my load right into her almost on cue. I turned her around and kissed her hard as we both moved under the shower's stream. We washed up and finished our shower. We got ready and decided we better go out to dinner before we started fucking again.



We went to a nice quiet restaurant where we were seated in a booth away from the few other guests that were scattered amongst the other tables. We had a nice view of the lake as the sun began to set. We sat next to each other. I looked at Emily and asked, "Where did you get the toy? You haven't left the house since you've been home and we just barely discussed trying new things."



Emily smiled, "When Jessica and I were in the kitchen making snacks we had a nice little conversation." A cold chill went through my body.



"The toy was Jessica's. We were talking about how Chris likes to dress in 'girlie' outfits and I was so caught off guard that I mentioned that you did too. Please don't be mad at me." I leaned in and gave her a kiss to reassure her.



"Mmm, that was nice. Anyway she also mentioned that Chris liked his ass played with and she even fucked him with a strapon. I was so intrigued that I asked her to tell me more. She said that Chris is exploring his bi side more and more. He actually likes getting fucked and wants to try it with a man. Jessica brought up the thing about finding the right couple to share this with but hasn't found them yet." I could tell that this was exciting Emily again and my hardon reminded me that this was turning me on as well.



We finished our meal and drove home. We were both sexed out so we just cuddled and went to sleep. The next morning I woke and Emily had left for work already. She left a note in the kitchen reminding me to check out some vacation spots. I called my travel agent and she was eager to search a non-business trip booking. I gave her my requirements of two bedrooms, two bathrooms, secluded, and must be beach front property.



I started to pound out some work of my own when my travel agent called me with the perfect spot. She said she would email me the pictures and price. She put a twenty-four hour hold on the place. It was one of the many smaller Bahamas Islands. The Itinerary was planned out as well. We would fly into Miami and from there catch a one hour hopper flight to St. Croix. From St Croix we would take a 30 minute puddle jumper to your own private one mile island. I called Emily and left her a message letting her know that Jessica and Chris would be home for dinner. Then I called Jessica and arranged for her and Chris to come over and see if they approve of the vacation spot.



I went to the store and grabbed four nice thick steaks and potatoes to bake. I tossed a nice salad and seasoned the meat. At about 4pm I popped the potatoes in the oven figuring they would take an hour plus and could rest for a few minutes. At 5pm I lit the bar-b-q up. Emily was home first and hurried to change out of her scrubs. As soon as Jessica and Chris arrived I threw the steaks on the hot grill. Emily passed out glasses of wine as Chris and I watched the steaks cook. We pulled off the steaks at a nice medium rare. Emily and Jessica had the potatoes on our plates along with the salad. We sat and had a nice meal.



"OK James let's see this place you've been dying to show us." Jessica eagerly stated.



I went and grabbed my laptop and attached my cable to the laptop and our big screen television. I opened up my email and then the attachment my travel agent sent me.



"As you can see this is actually a private island that is only about a mile long by one mile wide. This small island is one of seven hundred of the Bahamas Islands. This is a three bedroom three and a half bath house that overlooks an infinity pool. There is a master suite on either side of the house. Best of all, this all overlooks our own private beach. The water is crystal clear and if you look out into the water you can see the reef poking out the water's surface offering a natural fence line to keep the larger critters out."



"And just how long will it take for us to get to this bit of paradise?" Jessica was first to point out that we were on the Pacific side and this place is on the Atlantic.



"With the time difference added in, two hours for security, this will be about eight to ten hours in total depending on how long it takes to get the island transfers. If we take the red eye to Miami we will arrive around 6 or 7 in the morning. We grab a short one hour flight to St. Croix, then a small 30 minute flight to the island. We should be in heaven before noon." I explained.



Emily was quick to note the size of the island, "It's only a mile long with a house, where will the plane land?"



"The plane lands in the water on the other side of the island. There is a dock that the plane and boats come in on. There are two servants at the house, a husband and wife team that does everything. They live off the island so we only have them from 7am to 4pm. They clean the house, make the beds, and serve breakfast and lunch. They will prep dinner but we have to make it. The house is solar and there is no television. Is that private enough for everyone?" My sales pitch was complete.



"Now the big question, how much is this going to cost?" Jessica was concerned since she is still in school.



Now I am going to hit them with the closing statement, "Well my airline miles will get us all to Miami and St. Croix. We have to hire a private local pilot that takes people to the islands which isn't that much really, only a couple of hundred each. The normal price for this secluded island is $20,000 per week."



"That's 10k per couple. James I'm still in school and I can't ask Chris to pay my way, we are just starting our relationship." Jessica was panicking.



I smiled at her, "BUT, you didn't let me finish, if we leave the week after next I picked up a last minute cancel and we can have it for $10,000."



Chris turned to Jessica, "Look sweetheart five grand is no big deal. I have already given you my heart. Money is just what allows us to enjoy life. I just sold a 2 million dollar home that plopped 80 g's in my bank you think five grand is going break me?" Chris was bouncing around like a kid in a candy store. I was just waiting for him to start the whining 'please oh pretty please' bit.



Emily was going to be the toughest sale, "I just took a week off for Mother, I'm not sure I can arrange something on such short notice? I have to make some calls. Jess isn't your finals next week?"



Jessica was beaming, "Yep, and my schedule will be clear after that. I'm on board." Turning to Chris, "I'll have to work off my portion," as she blatantly squeezed his cock.



"I already cleared my schedule so M the final decision is yours." I focused all the attention to her.



"Gee thanks, no pressure in ruining everyone's fun on account of me. I'll do my best to clear my schedule. I'm 99 percent sure there will be no problem." Emily chimed back.



We all high fived each other and started to make plans. The next day Emily had arranged her schedule. Chris was a hold back for one day due to a house listing that hadn't closed on time. The girls decided that they would go a day early and check things out so that I would only have to change two tickets. The girls would take the luggage so we could just go through security and not worry about checking anything in. Things were falling into place.



The next week dragged for me as I waited for our trip. I grabbed the one luggage bag and asked Emily where my stuff was. She reminded me that we were on a secluded island packing swim suits and shorts didn't take up that much room. I grabbed the bag and we were on our way to pick up Jessica. I dropped the girls off at the airport and had the night to myself.



Chris called and said he would meet up with me tomorrow night and we can share a cab to the airport. I spent the day sending out notices of my vacation and then I cleaned out the refrigerator. I had the entire day left to myself. I was feeling horny, as usual. I went to Jessica's room and found my black leather corset and black panties. I slipped them on and felt like a slut. I twirled in front of the mirror. I sat at Jessica's dressing table and on a whim grabbed a bottle of red nail polish.



I shook the bottle and began my transformation. I started with my toenails. As the first stroke glided across my big toe my heart skipped a beat. I feverishly painted my other toes. Then I started on my left hand. I could feel the wet spot in my panties as my cock leaked. The right hand did not come out quite as nice. I don't know how women become so ambidextrous, I guess practice. I waved my hands around to dry the polish. I stood again in front of the mirror and held out my hands. I wiggled my red tipped digits at myself, I felt so sexy.



Something was still missing. I opened Jessica's closet and there was a blond short cropped wig. I blew on my nails a few more times before I grabbed the wig. I bent over, placed the wig on my head, and held it on as I lifted my body and whipped my head back. The wig fell into place. It was loose but stayed on my head. I would imagine the Jessica pinned it onto her real hair. I turned to look in the mirror again and was shocked at the transformation. I wasn't really passable, but I was stunning. I felt like a little sexy slut.



I called in for a pizza, grabbed a beer, and sat in front of the tube. The pizza came a half hour later and I could swear the delivery boy was checking me out. He did not show signs of disgust, it was lust. That really turned me on more. I get why women spend so much time to look so pretty, I almost came knowing I turned a guy on. I walked into the kitchen and glanced at my reflection in the window, "You are a sexy bitch." I laughed it off and figured in his line of work I'm sure he's seen it all.



Before I started on my second piece of pizza Chris was knocking on the door. I got up and let him in. "Oh Jamie you look stunning."



He went and grabbed himself a beer and joined me in front of the tube. We used paper plates and finished off the pizza. We had about two hours before the cab came to pick us up so we shucked our clothes and headed for a quick cooling off dip in the pool. After a couple of leisurely laps Chris came up behind me and pressed his hard cock along the crack of my ass. His arms wrapped around my chest as he ran his tongue up and down the side of my neck.



"Do we have time for me to fuck you before we get on the plane?" Chris breathed into my ear.



I moaned out, "Ya but I don't want to be dripping cum out of my ass during the plane ride. My luck some bitchy lady will be sitting next to me complaining about smelling fresh cum." I wiggled my ass against his cock and flipped him over my head.



Chris came up for air laughing. He dove under the water and I felt his mouth slide over my hard cock. The warmth of his mouth felt really good. Lucky for me Chris couldn't stay under long enough to blow me to completion. When he surfaced again I was already under the water and behind him. I slid feet first between his legs, grasped his ass cheeks, spread them wide open, and shoved my tongue into his tight rosebud. After a couple of good licks I started to lift him into the air using my face buried in his ass as leverage. I launched him into the air, not really that high his feet never broke water, but the pressure of lifting him allowed me to really get my tongue deep into his hole.

