First Time Cuckold Ch 05

Oscar started sucking my well fucked pussy with great zeal, licking up all the cum that Jordi had deposited. Jordi's cock was so big and thick that it had left me quite sore and Oscar's attentions were both soothing and stimulating. After about an hour and four orgasms, I reached the conclusion that I really enjoyed being sucked to being fucked.

Oscar looked up at me, his face dripping with saliva, cum and pussy juice and asked, "Do you want me to continue Bea? My jaw is a little sore but if you would like, I will keep sucking!"

I smiled down at the little feminized cuckold and said, "No, you did a real good job dear, you more than made up for your inadequacies in the cock department. You can run along now."

I laid back on the bed and drifted off into a luxurious sleep feeling completely relaxed and satisfied. I made a mental note, remembering Irene's offer to use his mouth anytime I wanted, to ask her if I could barrow Oscar for a few days.

The next morning while Irene and I were having coffee in the dining room, told me that she and Jordi were going on a little vacation on his yacht. They would be gone for about a week and she asked would I mind looking after Oscar.

I told her I would be delighted. I will tell my husband that I am going to visit some friends, pack a few things and stay at her place. I was really looking forward to the chance of having Oscar to myself and putting him through his paces obeying my slightest whim.

Irene then called Oscar into the room and told him that she and Jordi needed some alone time. They wanted to do some fucking without him looking on while he fingered his miserable excuse for a cock. She also told him that I would be staying with him and he was to obey my every command, without hesitation or face punishment when she returned.

Oscar, although he was not pleased that his wife would be off, publically fucking another man, realized he had no choice in the matter and simply agreed.

Monday morning, after explaining to my husband I need some "away time", I packed a few things and headed over to Irene and Oscar's home.

When I got there, Irene and Jordi had already headed off for their vacation and Oscar, who had taken the week off from work, was wearing his maid's outfit and was busy doing his household chores. He looked so cute all femmed up and busy doing the dishes, just like a good little housewife.

I noticed his mascara was a little streaked and realized he had been crying. I asked him what the problem was and he told me that although he was aroused by the fact that Irene and Jordi were having an affair, he was not happy that they had gone off to fuck in the sun and left him all alone.

I knew it was time to take charge and told him to stop what he was doing and to come into the living room. Next I told him to lift his skirt and drop his panties. He seemed a bit surprised but complied.

I looked down at his tiny, shaved penis which was now encased in a CB3000 chastity devise which only Irene and I had a key to and smiling, unlocked the devise. Immediately his tiny penis, swelled hard and was saluting me.

I then removed a tape measure from my purse which I had brought with me to humiliate Oscar with and had him measure himself.

"Four and a half inches," was his reply when I asked him to tell me what total erect measurement was.

"Not even four inches," I teased, "How can you expect Irene, or any woman, for that matter to do anything with your teeny wheenie? Of course she is going to seek out real men to make her happy. I know you suck pussy well but most women need to feel a big cock deep inside them to be truly satisfied!"

Oscar looked down at the floor, ashamed to look me in the eye. He knew I was right. I then made him tell me why his wife was off fucking Jordi.

"Because I'm too small to satisfy her." He meekly replied.

"That's right Oscar, "I replied. "Men like you have only two choices in life. Either allow their wives to fuck other men to their hearts content or spend their lives alone, playing with their little dicks and fantasizing that they are real men! You are lucky Irene allows you to watch and clean her afterward."

Oscar seemed to understand and agreed with me. I told him that he and I were going have a fun week and right now, I needed his tongue in my pussy. I told him to lie down on the floor on his back and I quickly removed my pants and panties and straddled his face.

First I slowly rubbed my already moist cunt across his nose and lips allowing him to inhale my scent. It seemed to act like an aphrodisiac on him and I laughed as I watched his hard little penis pop up with excitement.

I grabbed it and started stroking it as he licked and sucked my clitoris and stuck his tongue deep inside my pussy, which caused my juices to run into his mouth and down his throat. I let go of his penis before he could cum. I wanted him hot and needy as he continued to suck me.

He was good at sucking pussy and soon I could feel my orgasm start to rise from deep inside me. My whole body began to convulse and I pressed my cunt hard on his mouth squirting my juice and glazing his face with my cum.

I heard him gasping for air and realized in my passion, was smothering him. I quickly lifted my pussy from his face and he started taking in deep breaths of air. I reached back and felt his penis, now soft and gooey and realized he had cum without my touching him.

I got up and told him to go and clean himself up and reapply his make-up. I had only been there for an hour and already been satisfied by his cunt-lapping. This was going to be a wonderful week!

I had two girlfriends, Betty and Jan who were bisexual like myself and I decided that it would be fun to invite them over for dinner and really put Oscar through his paces. I told him to go to the store and buy the necessary items needed to provide a gourmet meal.

I called my two ladies who were more than please to come to dinner. I did not however, tell them about Oscar. I decided to surprise them. They both had husbands who not very interested in sex and I knew they would love to help my torment my little feminized suck slave.

Oscar changed into his male street clothes and went off to do the shopping. I decided to take a long luxurious bath. I was soaking in the tub when Oscar returned from the market. After putting the groceries away, I had him wash my back, shave my pubes nice and smooth, towel me dry and give me a nice long massage with sweet smelling lotion.

It was so nice having a nice little sissy slave to do my bidding. I had put his penis back inside his chastity devise after he had bathed and shaved himself smooth all over. Then I told him to clean the house and prepare dinner for three. I explained to him that I wanted him dressed in his sexiest bra, panties, garter-belt and stockings. He was to wear his pink maid's uniform with four inch high-heels. He was also instructed to apply heavy make-up and wear his blond curly wig. I then had him make me a martini and after drinking it, took a long nap while he prepared dinner.

I slept until six and was awoken by Oscar sucking on my toes as I had instructed him to. He was all dolled up in his pink maid outfit and looked darling in his blond wig and make up. "Good evening mistress," he mumbled while licking my toes, "May I help you dress for dinner?"

I told him that would be just delightful and he began with my panties and bra that I had chosen, then the black silk slacks, see-through red blouse and finally the black suede boots with the four-inch heels. He kissed each boot lovingly and hurried downstairs to make the hors d'oeuvres.

I went downstairs and after Oscar served me a martini, smoked some pot and relaxed while listening to some soft blues music.

At seven, the doorbell rang. I told Oscar to answer it and to be sure to curtsy to our guests. He was unaware who my guests were. I saved that little surprise for him. He knew both Jan and Betty from work and I knew, for them to see him in his feminized state would be especially humiliating for him. To make things even sweeter, they both disliked Oscar and I knew when they realized who my pretty maid was, would find it especially enjoyable ridiculing and humiliating him.

Oscar answered the door and turned bright red with embarrassment as he curtsied to the two women. They were both shocked at first, then, realizing it was Oscar, broke into hysterical laughter. Oscar showed them into the living room and I could see tears of humiliation running down his cheeks.

"Bea," Jan said, through her laughter, "What the hell is going on here and why is Oscar dressed like a sissy maid?"

I told Oscar to lift his maids dress and drop his ruffled panties and explain the situation to my two friends.

Oscar, still sniffling and blushing complied with my instructions. He raised his skirt and hooked his thumbs into the waistband of his panties and pulled them down below his knees exposing his tiny, encased penis which was made even smaller inside the chastity belt.

He then, unable to look Jan and Betty in the eye said, "My wife, eh, I mean mistress Irene has gone on vacation with her lover Jordi because she needed a real man's cock to satisfy her because my penis is too small and she cannot feel it. She has made me her sissy maid to remind me that I am not a real man and if I am good, she lets me watch her fuck other men and suck their cum from her pussy. She has loaned me to Mistress Bea while she and Jordi are away."

Jan and Betty were howling with laughter. Betty then said, "I always knew you were a wimp, Oscar but I had no idea just how big a sissy you really were!"

Jan stopped laughing long enough to add, "Look at his penis! I have never seen one so small. I think my clit is bigger than that! Tell me Bea, Just what did you have in mind for this evening's festivities?"

I told Oscar to fetch the girls some drinks and serve hors d'oeuvres. After he left, I explained to my friends that after dinner we could have some fun with Oscar. He was completely trained and we could make him do anything we wanted.

Jan and Betty loved the idea and we drank our martinis and discussed our plans while Oscar finished preparing dinner.

After dinner and few drinks later, Jan, Betty and I were really feeling the effects of the alcohol. We were getting horny and started shedding our clothing. Oscar was also getting turned on at the site of three naked women and I could tell he was feeling the pain of his tiny penis straining at the chastity devise trying to get hard.

"Is my sweet little maid getting turned on?" I asked Oscar? Oscar quickly nodded his head. "If I release you from you case, you must promise me you will not touch your little dick or drip any of your puny goo on the nice clean rug." I teased.

Oscar quickly agreed and I produced the key and unlocked his cage and he immediately became hard, reaching his maximum size of four and one half inches. He looked ridiculous in his feminized state and his little penis bobbing up and down.

Jan reached over and gave it a quick squeeze causing Oscar to moan with pleasure. She then slapped it very hard and said, "I think I would like you to suck my pussy sissy, would you like that?"

Oscar nodded his head and immediately fell to his knees and buried his face between Jan's legs as she leaned back on the couch. He sucked her with extreme abandon while she moaned and groaned in response to his manipulations.

Betty, who had been watching this spectacle, quickly strapped on a dildo which she had brought and after apply some lubricant, placed it at the opening of Oscar's asshole. "Beg me to fuck you bitch!" She commanded.

Oscar paused his pussy lapping long enough to reply, "Please fuck my man pussy Mistress Betty! I need you cock deep inside me!"

We all laughed at his eagerness and Betty plunged the dildo deep into Oscar's rectum.

"Aaaahhhhhh!" Oscar moaned as he felt the full length of the rubber cock penetrate him.

Betty was relentless as she continued to pound Oscar's ass with her strap-on.

Finally it was too much to bear and Oscar started shooting cum from his undersized penis as Jan came in his mouth. Jan was a squirter and soon Oscar's face was glistening with her juices.

I could feel my own orgasm cumming as I played with myself, watching the erotic scene that was unfolding before me.

We then made Oscar lick up the cum he had deposited on the carpet and while he laid on his back, Betty straddled his face as he sucked her to orgasm.

We continued to use and abuse Oscar for the rest of the night. We all experienced multiple orgasms and fell asleep in the wee hours of the morning, exhausted and totally satisfied.