tagTranssexuals & CrossdressersHome from the Resort

Home from the Resort


A couple of years ago I got into some serious gambling debt and wrote a bunch of bad checks in an effort to deal with it. My wife, Dawn, was very angry with me and stressed out by the situation that I put her in. One evening shortly after I was paroled from prison, Dawn, and I were sitting in our living room drinking wine. The alcohol had loosened up her tongue and she was giving me a bit of a lecture on her opinion of my prior behavior. I sat quietly sipping my wine, feeling guilty and only gave an occasional nod of my head. I thought she was largely correct and had a right to vent her feelings on me. As Dawn was winding down, the doorbell rang. When I opened the door I was shocked to see, Bart, a former inmate that I had hoped to never see again standing on the doorstep. Bart gave me a big leering grin and just walked in like he owned the place. I had never mentioned Bart to Dawn because to do so would be embarrassing and because I really wanted to put Bart and the prison experience behind me. Bart walked up to me and gave me a pat on the ass and told me that he had really missed me since I got out. Bart put his arm around my shoulders and began walking me into the living room.

Dawn gracefully lifted her petite frame from the couch as she gave her head a quick jerk that caused her blond hair to spring into motion and smiled at Bart. I could tell that he caught her eye from the way she looked at him. Bart was a handsome, well-muscled guy who was over six feet tall topping me by at least a head in height. He gave Dawn an appreciative once over and broke out into one of his charismatic smiles that pretty much got him his way with most people.

Dawn moved toward us as if drawn by a magnet and warmly greeted Bart, "I'm so happy to meet one of Jimmy's friends from the "resort." Resort was our euphemism for talking about prison.

Bart hugged me closer and replied, "Jimmie and I were very close when we were at the resort, as you say, together."

When Dawn got close to us, Bart let go of me and reached out and enclosed one of Dawn's hands in both of his hands. While holding her hand and looking into her eyes he said, "I had no idea that Jimmie was married to such a beautiful woman." Dawn smiled broadly and I could tell she was flattered by his attention.

Dawn offered Bart some wine but he declined saying that would appreciate a real man's drink, if by any chance there were any whiskey in the house. Dawn smiled and asked if some bourbon would do. Bart told her that would be perfect and she went into the kitchen to get the drink. When Dawn returned with the drink, Bart took the glass and sniffed the aroma of the evaporating whiskey. Dawn returned to her seat on the sofa and Bart took a seat beside her. I stood there for a moment not sure what I should do and Bart said, "Grab a seat Sweetie and finish your wine." I reached over and took my glass of wine from the coffee table and sat down in a near by armchair. Bart proceeded to charm Dawn with tales about his rather exciting life and experiences. Finally, the shoe dropped that I knew was coming.

Bart grinned and leaned down and whispered something into Dawn's ear and then glanced at me with a twinkle in his eye. For a moment Dawn looked shocked and then she giggled. Bart laughed and put his arm around Dawn and leaned in to whisper in her ear again. Dawn was obviously getting a bit inebriated from wine she had been drinking and was easily captivated by Bart's charm. There ensued a bout of whispering and giggling and laughing while I sat there feeling like an uninvited observer. Finally, Bart turned to me and as he patted the couch beside him said, "Come on over here Sweetie and join us on the couch."

I was reluctant to get within touching distance of Bart but then Dawn joined in. She caught my eye and with a knowing smile said, "Come on Sweetie sit with us."

I got up and sat on the couch so that Dawn was on one side of Bart and I was on the other. Bart put his arm around my shoulders and pulled me close to his side. Dawn then asked, "Is what Bart told me really true?'

I replied, "I don't know what he told you."

Bart laughed and said; "I told Dawn that you were my "wife" while we were at the resort and a damn good one at that, which is why I came to see you when I got out."

I was terribly embarrassed that he had revealed this to Dawn but she appeared to take it in stride and seemed more curious than upset. With a leering smile, Dawn asked, "Jimmy dear what sort of duties does a "wife" have at the resort?"

Looking down at the floor and in a meek tone of voice I said, "I did personal chores for Bart sort of like a servant."

Bart took a sip on his whiskey, laughed and said, "A wife's most important duty was to service her husband when he was horney." He gave my shoulders a squeeze, looked at Dawn with a shit-eating grin on his face and said, "Sweetie here gave better blowjobs than any other man or woman who has ever sucked my cock." Dawn giggled at this and was clearly enjoying my humiliation.

Dawn looked at me and in a stern voice said, "Well, Sweetie, while you were at the resort having fun with a hunk, I was working two jobs to get us out of the financial hole you put us in and living like a nun."

I noticed that Bart had become aroused and that his cock had swollen and was pushing against his pants clearly showing an outline of his erect member. Bart saw me looking at his lap and reached over and took my hand placing it on his hard cock and held it there. He then turned to Dawn and said, "After Sweetie here got out I couldn't find anyone who could suck my cock with the same gusto as Jimmie." Dawn giggled again and looked at my hand resting on Bart's hard on. Bart then asked, "Dawn would you mind if I had a little fun with my "ex-wife" for old times sake?" Dawn looked at me with that leering smile on her face and replied, "Bart I would never come between a man and his wife, especially if I get to watch."

"You're more than welcome to join us if you would enjoy seeing Jimmie in action. Hell, you might even learn something," replied Bart. He then took my hand and stood pulling me to my feet and said, "Lead me to the bedroom Sweetie. I can hardly wait to feel that tight throat of yours squeezing my cock." In something of a daze, I began leading Bart toward the bedroom. Dawn followed and as she entered the bedroom she turned on a small bedside lamp that dimly lit the room.

Bart said, "Get naked Sweetie." Feeling totally humiliated, I took my clothes off never looking up from the floor but acutely aware that Dawn was watching. Bart looked over at Dawn and asked, "Do you have some nice sexy lingerie that Jimmie could wear?" Then he added, "I really don't like sticking my dick in anyone that doesn't wear panties."

Dawn went to the chest of drawers and pulled out a pair of mint green panties and a matching slip and handed them to Bart and said, "I think your wife would look sexy in green."

Bart said, "Thank you. This looks perfect." He then turned to me and asked, "Don't you think these are sexy as hell?"

I mumbled, "Yes."

Bart laughed and commanded, "Put those panties on girlie boy." I stepped into the panties and pulled them up very aware of the silky, soft touch of them as they brushed against my skin. I then pulled the slip over my head and let it slide down caressing my skin as it slid down my torso. Bart spun me around and gave an approving smile and said, "You never looked this sexy at the resort."

Bart pulled me toward him, leaned down and gave me a long kiss on the lips. As he kissed me I could feel his hands cup my buttocks. He began rubbing the slip over my panty-clad buttocks. I could feel his hard cock pressing against my stomach and knew he was getting very hot. Bart released his grasp on me and said, "Assume the position."

I dropped to my knees in front of him and stared at the bulge in his pants for a moment. Finally, resigned to what seemed inevitable I reached up and unfastened his belt, unbuttoned his pants, unzipped his fly and pulled his pants down. Once his pants were down his swollen cock was nearly bursting through his underwear. I pulled his jockey shorts down and his large rigid cock sprung to attention pointing right at my face. I heard a little gasp of appreciation come from Dawn's direction.

Bart thrust his rigid member at my mouth, which reflexively opened to accommodate his cock as it had done many times at the resort. I began sucking on the soft head of his cock and then grasped the shaft at the base and raised the cock exposing the underside. I took the head from my mouth and began stroking the underside with my tongue making sure to get it very wet with saliva like I knew Bart wanted. I soon came back to the head, which was slippery with pre-cum now and began running my tongue around the head spreading the slippery pre-cum all over the head.

In the background I could hear Dawn's heavy breathing and knew that this was turning her on. When the head was nice and lubricated, I opened my mouth wide and thrust my mouth forward forcing the rigid cock fully into my mouth with the head pushing down into my throat. I now sucked down on Bart's throbbing cock and pulled my head back causing his cock to slide partially out of my mouth. I then plunged down again forcing the hot rigid flesh back down into my throat. After repeating this a few times, Bart grasped my face in his hands and began to control the action. I simply relaxed my mouth and throat and let him have his way.

In order to speed up his release and end my humiliation in front of Dawn I began to massage his balls. Soon I could feel his balls tighten and knew he was about to blow his considerable load. A moment later I felt the first convulsion as his cum began to spurt in large gobs from his cock. I could feel the warm, sticky cum spread out over my tongue, the roof of my mouth and slide down my throat. Bart sat back on the edge of the bed and leaned back on his arms while I licked his cock clean and then milked his dick with my hand until the last of his load oozed from the tip. I took the head of his cock into my mouth once again and gently sucked the last of his load from the head.

Bart opened his eyes gave a little sigh and looked across the room where Dawn was sitting. He smiled and said, "I hope that was nearly as much fun to watch as it was for me." He then added, "Jimmie is a real artist when it comes to giving head."

Dawn was sitting in a chair with her legs spread apart, her skirt hiked up, her hand down the front of her panties and at least one of her finger busily pleasuring her pussy. Bart grinned and said, "Give me a few minutes and I'd be happy to fill your wet pussy up with wildly thrusting man meat." Dawn withdrew her hand and thrust her wet fingers into her mouth and lustfully stared into Bart's eyes.

Bart sent me out to get Dawn another glass of wine and another whiskey for him. When I got back Dawn had moved from her chair and was sitting on the bed beside Bart. As I handed Dawn her glass of wine she reached up and wiped a small dribble of Bart's cum from my cheek. She looked me in the eye and slowly brought her finger to her mouth and licked the gleaming white fluid from her finger. She then giggled and asked, "Jimmie baby doesn't Bart's baby juice taste yummy?" I just stood there staring at her.

Bart said, "Answer the question Sweetie." I just nodded my head in affirmation. Bart grinned and said, "Jimmie loves to eat my cum." I handed Bart his glass. He took the glass and said, "Go sit in the chair in the corner and watch your wife get fucked by a real man."

They sat on the bed sipping their drinks and soon I noticed that Dawn had her hand wrapped around Bart's cock, which was growing rigid again as it became engorged with blood. Bart said to Dawn, "Go ahead baby and try the taste of a real cock." Without any hesitation she leaned over and filled her mouth with Bart's rigid cock. Bart soon pulled her off of his erect member and said, "I want to stuff your pussy with that cock meat." Bart laughed and then added, "Let's leave the cock sucking to an expert."

Bart stood and pulled Dawn up from the bed. He began to undress her and throw pieces of clothing toward me, which he told me to fold stack on the nearby dresser. After Dawn was naked, Bart picked her up and laid her on the bed. He spread her legs and began rubbing her pussy with his open hand and massaging the lips with his fingers. When his fingers were slick with her juices he plunged his fingers into her cunt and began finger fucking her. Dawn moaned and withered under his touch and was soon highly excited and thrust her pelvis toward Bart's hand.

Bart withdrew his hand and flipped her over on her belly. Next he spun her around so that she was lying across the bed and raised her hips. Dawn cooperated by drawing her knees up under her and sitting back on her legs while leaning forward with her forehead resting on the bed. This position left room for her pert little tits to hang down and swing free. Dawn's glistening pussy was exposed and ready to be filled. Bart stood at the edge of the bed and pushed forward bringing his rigid member into contact with Dawn's slippery tunnel. As Bart slid his hard cock into Dawn's cock socket, Dawn moaned in pleasure. The more cock Bart fed into her the louder she moaned. Soon Bart had her by the hips and was pushing his cock into her as though he was trying to reach her throat. Dawn fully impaled on the Bart's rigid pole began to move her hips and was soon fucking herself on the shaft of man meat filling her hole. I saw one of Dawn's slender hands sneak back between her legs and cup Bart's balls. Bart watched Dawn fuck herself with his tool for a few minutes and just when it seemed Dawn was wearing down Bart sprung into action.

Bart began withdrawing his cock from Dawn as she thrust back trying to retain his full length inside of her. Bart grasped her hips so that he could stop her thrusting and began his own thrusts. Bart slowly withdrew his cock until only the head remained buried inside Dawns pussy and then he would quickly push the full length into her. Dawn would let out a cooing sound from deep in her throat and then Bart would begin the slow withdrawal of his cock followed by another quick deep thrust. Dawn's body was soon quivering as orgasmic waves rippled through her body. Bart then began fucking Dawn so hard that I thought he would hurt her but as his rigid tool pounded her pussy making sucking and slurping noises as it rapidly ran in and out of her cunt she squealed with joy and urged him on telling him to fuck her harder. Bart did his best to comply with her urging until he suddenly jerked and thrust deep into her pussy as he shot a load of cum that took several spasms to pump out of his balls. Bart fell on top of Dawn and then rolled so that they were in a spoon position. He kept his cock thrust deep inside her while cupping her tits in his hands and gently massaging them and occasionally rolling her erect nipples between his thumb and finger. Dawn's reached several more climaxes before Bart finally pulled free and turned his attention toward me.

In a commanding voice Bart said, "Get over here and take care of your wife."

I came over the bed and asked, "What do you want me to do, Bart?"

He pulled Dawn around on the bed so that her legs were hanging off the side. Dawn was lying with her eyes closed and a beatific smile on her face. Bart spread her legs and said, "Lick that pussy clean." I kneeled down between her legs and began licking her pussy, which was slippery with her juices and Bart's cum. I thrust my tongue between the lips of her pussy in order to reach more of the juices still oozing out of her cunt. Dawn soon responded to my ministrations and I could hear her moaning with pleasure. While I was cleaning up Dawn, Bart said, "You can eat Dawn's pussy anytime she wants it but you are not to fuck my woman." Dawn gave a little shutter as she had another orgasm and Bart reached over and grasped my hair and pulled me away. He pulled my face into his crotch and said, "Tongue clean my dick now, cocksucker." As I began licking his dick clean of Dawn's juices and his cum I noticed that Dawn now had her head resting on her hand, which was supported by her elbow pushed into the mattress. She watched in apparent fascination as I licked Bart's cock and balls clean.

When Bart was satisfied with the job I'd done, he pushed me away. He looked a Dawn and said, "You are the best fuck I've ever had. I don't know how a girlie boy like Jimmie could have ever satisfied you."

Dawn grinned and replied, "My girlie boy never fucked me into oblivion like you just did."

Bart said, "Well, I need a place to stay so why don't I just move in with you and I can bang your brains out every night."

Dawn giggled and said, "I would love to have a man around the house."

Bart asked, "Do you think you can help Jimmie learn how to look like the cock-sucking slut he really is?"

Dawn replied, "I can make him look just right for the part." She added, "It's about time I had some fun around here."

Bart smiled and said, "Get that bitch looking hot and I know plenty of guys that will pay well to pump a load or two down a good looking girlie boy's throat. I think that should cover all of the household expenses and leave enough for us to go out and have some fun."

Dawn said, "I'll have Sweetie here looking like sexy slut in no time.

Bart replied, "You can quit your job and take over managing Sweetie full time. I think he's going to be very busy sissy boy. Don't let the hot little bitch get off without permission. Jimmie will give better blowjobs if he is horney.

Dawn giggled and said, "From now on I'm your woman and I'll keep your resort wife looking good and faithful to you."

Dawn then said, "Jimmy, you are going to pay dearly for all the hell that you put me through." She threw me one of her satin nightgowns and told me to get ready for bed. After I had changed into the nightgown, she said I should make a pallet at the foot of the bed in case she or Bart needed me during the night. After making up the pallet, I settled down and tried to go to sleep but I was kept awake by the sounds from Bart and Dawn's activities in bed. I was also so horney I could hardly stand it and wanted to jerk off for a little relief but knew that if I did I be in big trouble with Dawn. I finally drifted off to sleep and had a dream about being on my knees, naked except for a pair of pink panties and in the middle of a gaggle of men all of whom had erect cocks sticking out of their pants, lust on their faces and a hundred dollar bill clutched in their hand. Dawn was working her way around the circle collecting the money and assuring each customer that they were about to have the best sex of their life as she gave, in turn, each cock a little squeeze with her hand as if to prime it for action.

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