An Unforgettable Vacation

An Unforgettable Vacation An Unforgettable Vacation

Status: Finished

Genre: Erotica


Status: Finished

Genre: Erotica



I met Angela after my wife died. She had gone through a bad marriage with a mean-spirited man who put her down all the time. I was an emotional mess as well. As we spent time together, A sexual relationship developed that neither of us saw coming.



I met Angela after my wife died. She had gone through a bad marriage with a mean-spirited man who put her down all the time. I was an emotional mess as well. As we spent time together, A sexual relationship developed that neither of us saw coming.


Submitted: October 07, 2016

A A A | A A A


Submitted: October 07, 2016




In order to tell this story a bit of history is in order. My first job out of college was at a large hotel in Atlanta. I worked in the catering department and helped people plan conferences and conventions. One day an amazing woman came in from a large group that was planning a convention. It was my duty to give her a tour of the hotel. She was an extremely large woman. She had beautiful red hair, pale, white skin and she was covered with freckles from head to toe. She had a fantastic hourglass figure. She was wearing a green velvet dress and tall heels with straps around her ankles. I could not keep my eyes off of her. I was  23 at that time and I would estimate her to have been in her late forties.

We talked while I showed her around the hotel and I found myself flirting with her shamelessly. I had just gotten married, but I could not keep my eyes off this woman. I showed her some hotel rooms then we went to the large Presidential Penthouse suite. As we were about to leave she turned toward me and said, “Not many men flirt with me like you have and it has really turned me on.” I looked deeply into her luscious green eyes and kissed her passionately on the mouth.  Then I apologized. I was so embarrassed.

She put her arms around my neck and began kissing my face and neck. I felt her breath on my ear. “I’m not wearing anything under this dress.” She whispered. I reached down and slowly lifted her skirt until I could get both hands on her naked ass. I edged her back to the dining table and laid her back and lifted her legs and I sucked her and licked her until she climaxed. I won’t bore you with the rest of the story but I include it here to illustrate how my fascination with BBW’s came about.

So, fast forward twenty  years to December two years ago, two  years after my wife passed away. I was feeling quite lonely and was feeling sorry for myself. A friend of mine invited me to one of those dreadful New Year’s Eve parties that no one wants to go to. The weather was mild so I went outside and sat in a chaise lounge beside the pool. The pool was covered and I watched leaves and debris blow across the surface of the mesh cover and sipped my scotch. After a while I heard the door open behind me and heard footsteps. Out of the corner of my eye I saw a large woman walk by the pool. She didn’t see me. She sat down at one of the tables and sipped her drink. I perceived she was crying. Then she spotted me.

“Oh, I’m sorry,” she replied, as she dabbed at her eyes with a cocktail napkin. “I didn’t mean to invade your solitude.” I assured her it was not a problem. “I’m Sean.” “Nice to meet you, I’m Angela.” She stood and walked toward me and sat on the end of the chair next to me. She held up her glass for a toast, “For a great year,” she whispered. We clinked our glasses. I waited for her to speak. She had on an intriguing perfume. It was quite intoxicating. I later found out it was Mitsouko. She was wearing baggy clothes and some awful shoes. Her haircut looked like a school kid had done it.

But, she had a very sexy face. Even in the moonlight I could see her flawless, porcelain skin and bright, sparkling green eyes. I immediately wanted to take her to my salon for a make over. Well, to make a long story short, we left the party and went to a little bar that played jazz and we talked until early morning. I wasn’t attracted to her physically, but intellectually she was a homerun.  She was an attorney, but obviously gave no attention to her appearance at all. I disliked her ragged, chipped fingernails.

Over time, we over came these issues and we started dating.  This brings me to the trip we took to the Bahamas a few weeks ago which was about a year after we met.  We splurged for a bungalow on the ocean with a huge covered porch and swimming pool. We had an amazing time. We ate lobster and drank expensive wine every night. We had some mind blowing sexual role-playing adventures along the way. We only had one issue during the trip and it was easily solved. She snored. I snored and I got up several times each night so eventually we ended up in separate bedrooms.

During the twelve months we dated and spent time together, she confided in me that her husband had put her down for her curves and had forced her to “cover up” as she put it. She wasn’t a victim, but I can tell you that guy really damaged her self-esteem. I did eventually take her to the salon where I go and they styled her hair and gave her advice on her make up. She also began regular manicures and pedicures.

On the morning of the last day of our trip, I was awakened and I felt my wrists were tied. She was straddling my legs and was kissing me. This was outside the scope of our story telling. She had not talked much about BDSM at all. I’m not into pain, but some light bondage never hurt anyone.

I had the blackout drapes drawn and the room was pitch black and I could not see anything. I could feel her face only inches from mine. “Good morning.” She began kissing my face and licking my ear, which is my Achilles heel. I could feel something leather against my cock.  She was whispering in my ear.

“I woke up this morning feeling really bitchy and horny so I am taking control of our last evening here.”

I didn’t say anything as she continued to kiss me, probe my mouth with her tongue and lick my ear lobes.

She pressed her crotch closer to my cock. “Do you like my leather panties? It feels like you do.” She laughed. “It’s our last night here and I have some really fun surprises for you. You are going to be dominated tonight baby. Is that what you want?”

“No,” I said. She laughed. I think you will like what I have planned. Do you trust me?” I assured her I did.

She slid back and took hold of my cock. She was wearing leather gloves. She began stroking me and squeezing my balls. “You were very thoughtful to arrange a spa day for me today,  and to show my appreciation I am going to be your dominatrix  tonight. Have you ever been dominated.” She continued to squeeze me and stroke me. “No.” “No, of course not, you’re always in control aren’t you? You’re the CEO and you always call the shots. But, tonight, I’m in control of you.” She laughed. “I think your cock likes what I’ve been saying, even if you don’t.”

“Here are your instructions. You are going to meet me here at precisely five o’clock. You are going to serve me and you will do whatever I instruct you to do. Do you understand?”


“For today, that will be, ‘yes, mistress Desiree,’ from now on. Desiree is my alter dom ego just for your information.”

“Yes, mistress Desiree.”


Her hands began moving faster and faster. My back arched and my entire body tensed up, but she stopped stoking me.

“No! Do not climax. You’ll have to wait. She untied my hands and stood beside the bed. “Now kiss my ass!”

I knelt on the floor and began licking her thighs and ass and I kissed every inch of it. She abruptly pulled away and walked to the door.

“Do not jerk off, I want you hard for me this afternoon.”

I lay back down. My cock was throbbing and my balls ached to be released but I got dressed and went for breakfast. I spent some time at the beach and met some guys whom  I had met at the pool in the late afternoon to play cards. But I could not get Anne, I mean, Desiree out of my mind. They all asked me why I was so distracted. I blew them off and counted the minutes until five o’clock.

At five, I excused myself from the game and walked across the property to our bungalow. My mind was racing trying to figure out what she had planned. I swiped my key and went inside. All of the drapes and blinds were drawn but I could hear her in her bathroom. At the end of the hall there was a chair with clothing on it. There was a stiff white card with “wear these” written on it. I was shocked when I held up a black and white French maid’s costume. I undressed and put it on. There was a pair of black thong panties as well.

“You’re taking way too long.” She yelled from the bathroom. “I need a drink.” I walked down the hall. She was in the large sunken tub with bubble bath up to her neck. She was holding up a champagne flute. I got the bottle from the bucket and poured her a glass.

“You may have a glass too, sub.”

I poured myself a glass and sat on the vanity stool.

“Lift up your skirt.” she instructed. “Is that dick hard for me?”


She raised her eyebrows.

“Yes, mistress Desiree.”

She drained her glass and pointed to a bottle of body gel and a washcloth. She turned away from me and lifted up her ass. “Wash me off baby.”

I poured the gel over her ass cheeks and began moving my hands in a circular movement, squeezing and caressing her huge white ass. I took my finger and moved it between her cheeks, then I rinsed her thoroughly. She turned again and got on her knees facing me and threw her shoulders back. “Don’t forget these.”

I squeezed the soap over her chest and went wild squeezing her and sliding my hands all over her luscious tits. “Take it easy there baby, we have a long evening ahead of us.”

I rinsed her with the shower want attached to the faucet.  “Now for the best part.” She slid back and sat on the edge of the tub and moved her legs back. “Don’t forget this big juicy pussy. She poured some of the gel between her legs and handed me a razor. “Let’s get it smooth.”

I rubbed the soap all over her and worked it into a lather then carefully moved the razor with her guidance. She normally kept  this area very smooth but I carefully touched it up so that it was amazingly smooth. She got back in the water and I filled her glass again. “I’ll summon you when I’m ready to get out.”

I went to the living room and sipped my champagne. My mind was going through all of the things I planned to do to her after we got back from dinner. Shortly, she called. She stepped out of the tub and I dried her off. She sat on the vanity stool and lifted up her leg. “I believe my nails need a touch up. I want my body to be perfect tonight.” I knelt down and dabbed the bright red polish on each toenail.

She then led me to the bedroom. “Would you like to help me dress?”

“Yes, mistress, Desiree.”

We let her nails dry then she led me to the bed, she had three outfits laid out. One was a red and white sundress with a very low neckline and bare back. There was a pair of red lace crotch less panties and a pair of tall red sandals. The second outfit was a lavender sweater with a low neckline and a lavender leather skirt. A lavender half-cup, push up bra and matching panties were with it along with a pair of Lucite platform heels with lavender ribbons to wrap around her ankles. The final outfit was a white dress that laced up on each side. It was short and very low cut. A pair of tall white platform sandals lay beside the dress.

“Okay, baby, which do you think I would look sexiest in?” I picked up the white dress. “Oh good, that’s my favorite because I can’t wear anything underneath.” Her robe dropped to the floor and she stood before me naked. I felt my cock jerk. “Would you like to eat me right now?” “Yes, mistress, Desiree.”

“Okay.” She sat on the edge of the bed and moved her legs back. I dove hard to the floor and I had my mouth on her before she sat down. “Oh you like that pussy don’t you sweetie? She stopped me. “Look at me.” I looked up into her eyes. “How would you like to see a big hard dick in my pussy? Would that turn you on?” I went wild. I continued to suck her and lick her. She grabbed my head and climaxed squirming wildly on the bed. “Oh I do love for you to eat me when you are turned on.”

She pulled the dress on and I tied it on each side. She looked amazing with a strip of bare skin on each side of her body. I knelt down and slid her shoes on and tied them for her. “Let me get cleaned up and dressed and we can go for dinner,” I said.

She walked toward me and took both of my hands. “No, sweetie, I’m in charge of the evening, remember?” She pulled me to the bench at the foot of the bed and took my hands. “I’m going out to dinner. You’re going to stay here and get everything ready.” “Ready for what?” “We’re going to have a visitor.” I was confused.

She laughed. She took my face in her hands. “You’re going to be my cuckold tonight. You are going to watch me get fucked right here on this bed.”

I was speechless.  It dawned on me that she was setting up a role-playing situation. I thought she was just telling a story.

“Now, I have to hurry, come, we both have to get ready.”

She led me to my bedroom and there was some lingerie on the bed. You finish getting  dressed and come to my bathroom when you are done.”

I put on a black lace garter belt and black stockings and pair of tall black heels. I walked toward her bathroom. She was finishing up her make up. She took my chin and I felt the lipstick go on. Then she put a blonde wig on me.  “This is going to be a night you will never forget. She lifted up her skirt and pressed her fingers into her pussy and she moved them around. Then she smeared her juices all over my face and moustache. “Smell that cunt while you wait on me.”

I heard a knock on the door. “I must be going. Your instructions are on my bed side table, I will see you later.” I stood behind the doorframe and watched her walk to the door. A tall handsome man I had seen at the pool was standing there smiling. She rose up on tiptoes and kissed him, smearing lipstick on his lips.

I sat in the living room sipping a scotch. The sun had gone down. I could smell her pussy on my moustache. I tasted it. There was a breeze blowing the sheer drapes. The only light was the moonlight slanting in the window. I was angry. I was angry that I was so turned on. I had thought about being a cuckold for years. I wasn’t sure what it was about watching her with someone that turned me on so much. I heard something at the door.

I ran to the bedroom. They came in and he grabbed her and pressed his face between her tits. “Slow down, lover.” she cooed. She called for me. It dawned on me that I was dressed in the wig and costume, but I was trapped. I walked into the foyer. She introduced us. “Go pour our guest a drink, get him a robe and then come to help me in the bedroom.”

I got the robe and draped it over the sofa and poured him a martini from the pitcher. Her instructions had all of the details. I walked into the bedroom. She put her arms around me. “Have you been thinking about watching me?” I nodded. She smiled. “Quick help me get undressed. I undid the lacing on the side of the dress and helped her out of it. She sat on the edge of the bed with nothing on but her heels. She moved her knees back, her cunt was glistening and wet. “Lick me.” I did. “He finger fucked me during dinner, I had a glorious climax. Lick me clean.”

She pushed me back. “Okay, now get me ready for him. My outfit is in the dresser.” I pulled open the drawer and saw the black lingerie. It was a black satin bustier that laced up the front, thong panties, a black wig, and a lot of make up and a pair of thigh high boots. She turned and told me to put the bustier on her and lace it up. “Fit those big tits in there, baby so he can get at them easy. You know, I have never been as excited in my life. I’m going to fuck him good for you.”

She pulled up the boots to complete the outfit and positioned the wig, then she began layering on the make up. Silver green eye shadow, mascara and thick, glossy lipstick. “You are going to be my little cuckold tonight sweetie. Now kiss my ass!”

We walked out to the living room and she sat down beside him on the sofa. He pushed her head back and kissed her hard. I could see their tongues moving. “Get us drinks baby.” I poured the drinks. “Sit over there so you can see what he does to me.” I walked to the chair I had set up across from the sofa where they sat.

His hands were all over her. She slipped down to the floor and moved between his legs. She pulled his robe back. His cock was sticking straight up. She ran it over her face, then her lips. Then she licked it, the full length. She licked and sucked his balls  which were shaved smooth. “Why don’t you have smooth balls?” she asked me as she licked and sucked them..

I watched her lips go over the head. He was yelling and moaning. I watched her go down inch by inch.  She stood up and led him over to a long bench she pushed him down and swung her leg over him and moved forward I could see his head beneath her. Then I could hear him sucking her. It was loud. She grabbed my arm and pulled me in front of her. She put her arms around my neck, his face was below us. “Watch him baby. Watch him slurping that juicy pussy. Now kiss me. Kiss me while he eats me. Listen to him.” She began moving her hips. “Oh, this is so good.” She ground herself on him and she grabbed me. “I’m going to cum, hold me and kiss me.”

Her body went tense and her back arched and she began moving her hips back and forth. Then she screamed out. Then her body went limp. “Wow, that was awesome. Get us drinks baby.” She lifted off him and led him back to the bedroom. Her juices were smeared all over his tanned face.

I carried the drinks back to the bedroom. She again, had him laid back on a bench and his cock was deep in her. “I couldn’t wait, sweetie.” She took the drink and drained it. “Kiss my ass while he fucks me.” She saw the look of horror on my face. “Do it!”  I knelt down and began licking her huge ass. She was bouncing up and down on him. All I could see were his huge balls below her ass cheeks.

She leaned forward and rubbed her tits on his face and he was sucking and biting them hard. She grabbed my arm. “I want both of you in me!” She shoved me behind her. I moved up between his legs and slid my cock right up her ass. Both of them screamed and moaned. “Can you feel him in me, baby?” She started moving her hips as she moved up I went in. “Don’t stop, fuck me!” she yelled. I grabbed her hips and started pounding her. Finally I heard him start to climax. Then I did, then she did. I could feel her squeezing my cock deep inside of her. I didn’t move. I didn’t want it to be over. She was breathing hard. I didn’t move. Finally my cock slid out. I sat on the bed. She rose up and sat beside me. “That was amazing.” she announced.

We never did anything like that again. We enjoyed lots of role-playing, but it was just the two of us and lots of costumes, lingerie, shoes and assorted toys.


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