A Desire Finally Achieved

Monday - February 20, 2006

Authors note: The root of this story is in Chapter 01 - Blondes in pursuit of black guys. This is the ninth day of a fourteen-day vacation where fantasy has become reality. It is taking place on the island of Jamaica. What else do the stars have for me the remaining days here in paradise? If you have already read previous chapters, then you have a hint.

It begins:

I fight to get my eyes open and see Randy with his head down between Amy's legs. My pussy twitches just from imagining the feelings that Amy is experiencing. Randy has her legs up and spread wide open for full exposure of her toyland; his arms are wrapped around them, holding her succulent lips open with his fingers so he can get at the clit for maximum stimulation. I hear soft moans coming from Amy.

God I wish he was doing that to me.

She is cupping her breasts and with her fingers, she is pinching the nipples.

God, my pussy lips are filling with blood seeing my best friend being sent to Pleasureville.

I then feel an arm swing over me and a hand cupping a breast. "Good morning sleepy head." It's a female voice, so it must be Sammy.

"Roll onto your back, sweetie." I roll and we smile at each other.

"Hi, Sammy."

Sammy begins to mess with my nipples, alternating between sucking them and rolling them with her fingers. She sucks my left nipple and bites it while she pinches the right one between her thumb and fingers. We deep throat-kiss from time to time. My pussy lips are now throbbing with so much blood there.

"Randy tells me your juices are awesome. Can I get a sample? Do you want to 69 or would you rather just have me do you?"

"Let's 69."

"Heather, may I have top please?"

"Sure."

"Heather, so you are not surprised I like to use both hands to hold your lips apart and expose you clit to the fullest. When you are ready to cum, I will suck your clit into my mouth and flick it with my tongue, while at the same time finger fucking your pussy and ass."

I roll over onto my back and scoot down on the bed. Sammy lifts herself over me and lowers her pussy to my mouth with its swollen lips and dripping juices.

Her mouth dives onto my pussy.

I wrap my arms around her thighs so I can open her lips and get more tongue onto her clit. She is doing me the very same way.

I try my best to concentrate on her clit.

I am building with her tongue working my clit. God the delicate touch of her tongue; soft moans emitting from her lips are vibrating the whole area, causing me to build; I am extra hot with the anticipation of fingers going into both openings as it happens.

I hear Amy cumming.

Sammy breaks momentary contact and asks Amy to save the cocktail.

She returns to my clit and senses I am ready to have an "O". Sammy begins to finger fuck my love tunnel and ass after taking her hands from my lips. Her tongue is flicking my clit as my hard little nub is being drawn into her mouth like huge vacuum machine sucking it in. I am getting off with her mouth at my clit and fingers in the two lower orifices doing me there. The sounds are just like a guy fucking me with his cock. The moans and groans are telling everyone that might be listening of the pleasure I am sensing from this love making with Sammy.

My mouth is sucking her juices as they pour from her, as she is cumming. God, she tastes different too. I wonder if it is natural or a cocktail from some guy like maybe Randy. The flavors are not objectionable, just different.

We come down from our cum. Sammy is saying, "Randy was right. Your juice is delicious tasting."

Sammy moves to the other bed so Amy can deposit her cocktail mix into her mouth.

We shower. When we come out of the shower, my heart leaps because Trudy is sitting here sipping coffee. She says, "How are my special guests and lovers doing this morning?" I blush.

Trudy says, "Heather, your blushing shows you still have some innocence in you. Please join me for coffee or juice. Watch my lovers turn me on."

My eyes bug as they proceed with turning Trudy on by pawing all over her body. Four hands and two tongues are attacking her as if they desire to rape her.

When Randy's cock is back at attention, he walks over to the bed and lies down on it with his feet facing us. Trudy walks over, swings herself on top of him facing us, and lowers herself onto his pole letting out a meowing sound as it is slipping into her ass.

He uses his hands to support her as she lays back. God all her privates are exposed to us. Swollen pussy lips, glistening with juices, frame a gaping hole needing to be filled. I can smell myself leaking again. Randy is fucking her ass this way, pinching, and massaging her breasts and nipples. She manages to turn her head enough so that they are tonguing one another. We can see a river of juices flowing from Trudy's pussy. We see Trudy break the kiss with Randy and says, "Now Sammy!"

Sammy walks to the bed, lowers her face into Mistress Trudy's snatch and we hear, "Slurp, slurp, slurp as Sammy is sucking up Trudy's juices.

Then we hear, "OOOOO...OOOO...OOO...OOOOO!

"AA...AAA...AAAA...AAAAA!

"UUUUUUMMMMMM!

"OOhh...Ohhh...Ooooooohhhhh! Yes lover, Oh my Lover!

"Deeper, Hon' deeper, Oh deeper, Yes, Yes, that's it!

"Ohh...OOhh...Ohh...!

"AAA...AAAAA...AAhhhh...Ahhhhhh!"

Sammy must be tongue fucking Trudy's pussy and drinking her juice in order for Trudy to cry out as she is.

Sammy is massaging her clit with one hand while the other is somewhere else.

They stay in the same position and come down slowly with a lot of heavy breathing. When it is back to normal breathing for all three of them, Sammy heads for the shower. I do not realize that I masturbated myself to a cum watching the scene. Sammy winks at me as she passes me looking directly at my crotch with my fingers still in my pussy.

I run behind her to the shower and I notice Amy sitting there too with her finger still massaging her clit, legs spread wide, with her eyes closed, pinching a nipple and emitting low moans.

Entering the shower, Sammy is waiting for me. She grabs my face and we kiss. While kissing, she is passing some of Trudy's cum into my mouth. My knees nearly fail me.

We stand under the water that she had started and finger each other to another orgasm to get the day off to a good start, while French kissing in the process. As we are cumming, the others walk into the shower. They just grin and Amy says, "Am I in heaven?"

As we continue to shower, I ask Trudy if I could discuss something with her later.

"Drop by and we will have lunch and chat."

"Thanks for the offer, that will be nice."

Amy and I get dressed and head back to our bungalow.

As we are going in, guys are coming out. I say, "Judging by those smiles it must have been good."

Sam responds, "Almost as good as you two." Jeff hugs Amy and me tightly with a cheek kiss. I giggle again but again it was public.

Amy and I high five each other as they say, "Have a great day!"

We go inside. Jenn and Stace look at us. Jenn says, "Well it appears something set you two on fire with that glow that is all around you."

Amy responds, "Yeah, more than one fire was set."

"I am going to get caught up on my diary. See you all later."

Above entered: February 20, 2006 Day 8 - 9 Before lunch at our bungalow in Jamaica

I am getting cold feet about approaching Trudy alone to discuss Terry. I go to the telephone, call Frank, and ask him if he would accompany me. "Sure, babe," is his reply. I will swing by your place at 11:30 to pick you up.

Sure enough, he is here on time, along with Ann. He looks at me because I am sure I have a surprised look on my face and he explains, "She trusts me with you but we figure having one more supporting you and that person being a female like Trudy, might soften her business attitude some."

I run up to Ann and hug her. "Thanks, Ann, you are the greatest."

Off we stroll to Trudy's. As we pass others at the resort we need to wave back to all those that are still yelling out, "Way to go ladies."

When we arrive at Trudy's office, she is surprised to see Ann and Frank with me.

I say, "Trudy, I have a case of the nerves after this morning and asked Ann and Frank here because you have a lot of respect for them."

I begin by telling her how terrible my friends and I were in our treatment of Terry.

I continue by telling her about Terry's dilemma as he expressed it to me in confidence and his desires.

I mention to her about my Internet search and finding a place where he could get his dream come true at a reasonable cost.

I follow by telling her that I approached Ann and Frank since I had some money, and wanted their help to get Terry whole. After a lot of discussion with them and because of how things have fallen into place they agreed to help me.

"However, for me to get my wish and Terry his wish, we need your help now. Terry needs three months off from his job here at the resort. First, he needs to go to Bangkok for surgery. After the surgery he, now a she, needs three months of therapy. Ann and Frank have volunteered their place in Brazil for the therapy.

"My request to you is can you give him a three months leave of absence?"

Frank speaks, "Trudy before you ask questions or answer anything, I have confirmed what Heather has told you. She does not even know this but we have spoken directly to the doctors there that would perform this surgery. Ann and I are really in support of Heather; she and her friends have caused so many good things to happen for many of us. Unfortunately, Heather is not a surgeon to help Terry out directly herself in this particular matter. To this point in time, Terry is unaware of any of this planning."

As Frank is talking, tears are welling up in Trudy's eyes. When Frank finishes she gets up from her chair, comes over to me, and offers a big hug. She has some tiny sobs.

After she regains her composure she wipes the tears and says, "Heather I am ashamed of myself. It is only because of Terry's uniqueness that he has a job. Many of the guests have done the same as you girls did and leave him nice tips."

"How can I say no to such a humanitarian gesture on your part with the support you have behind you. Yes, Terry can have as much time..., God do I say, she or he, needs."

Tears begin rolling down Ann's and my cheeks. I see a tear or two streaming down Frank's cheeks. Ann and I get up and go to Trudy to hug her and cry.

"Thanks Trudy, thank you very, very much. You are just so sweet."

After regaining some composure Trudy then asks, "When do you plan on talking with Terry and asking him if he desires to do this?"

I say, "Maybe I will invite him for dinner and then tell him I have dessert waiting and surprise him with the offer."

Frank says, "Heather, might I suggest that you need to be 100% convinced this is what he wants and not you. I think it will be more effective if you can get him to take a walk on the beach after dark. After some chitchat strip and allow him to see you naked. Ask him, "Do you really desire to be a female like me and have guys fuck your brains out?

"Take his hands and run them all over your body. Run his hands up and down your pussy, drip hot pussy juices on them, make them slick, have him lick his hands then for the flavor. If he does not rape you after that treatment, then yeah, he needs to be a woman. Make him convince you he wants to be like you. If you sense that he really does then make your proposal. If you sense any hesitation, you had better not do it, because once they cut his cock and balls off there is no returning it.

"Heather, if you decide it will be a go, come with Terry to our bungalow afterward for a small party."

I sit here and shake my head. Trudy asks, "What's wrong Hon'?"

I respond, "This guy really covers all the bases. He is so gifted."

Ann says, "Yes he is, Heather. He covers my base so nice and I have seen him cover yours and as far as gifted goes, well we have all experienced that too."

We all laugh. I walk over to Frank and hug him.

Frank continues, "He will have his cell with him. Ask him to dial 2244, if it is a go. It will ring our bungalow. We then will know you are coming with him with an affirmative answer. Who else should we invite for the party?"

"Oh, Frank, I think it will be such an intimate time that it may be best for just you, Ann and Trudy to share the moment with him and not over whelm him, until the reality actually sets in for him. If he accepts the offer, he may not desire anyone to know but people that absolutely need to know."

Ann spoke, "Fantastic plan, Heather."

I say, "Ok now I need to get him to take me to the beach."

Trudy goes to the TV, looks at Terry's schedule, and then calls the reservation number for Terry.

"Hi Terry, it's Heather. Would you like to take a stroll on the beach with me tonight at 8:00? Let me know, later sweetie."

I bet when you get back there will be a message saying, "My God, yes, Heather."

"Well let's eat," Trudy says.

She pushes a button, doors open and food is delivered. We eat but do not discuss Terry any more because of the other employees' ears around us.

Trudy says, "Heather, I have been asked to do my skills in the Dungeon this afternoon. You have never asked many questions about it. Maybe what you saw was the extent of your curiosity. If you'd like you may sit in the theater and watch the show. It will be somewhat a deeper side of sex than what you have seen or done, I think. Why don't you bring your friends so they do not miss out on it?"

For some unknown reason, I look at Ann for some sort of signal and she nods her head yes.

"Come around 3 PM with your three friends or fewer if some are busy. The show may be in progress; well I need to prepare so see you later."

We give each other hugs and walk back to the bungalows.

I mention the three o'clock performance to my friends and they all agree to go.

I look at the clock and it 2:15 PM so I have some time.

Above entered: February 20, 2006 After lunch at our bungalow

We go to the Dungeon and make ourselves comfortable.

We see a black girl and a white girl kissing. Many candles burning light up the room. The only furnishing in the room is a large sofa. The girls are getting more and more into it and begin peeling their clothes off; they then get into some heavy petting and tonguing.

They move to the sofa and are now 69ing. As they are coming down from their cum, the door to the room opens and there stands Mistress Trudy in a red leather outfit. She is all covered in skintight leather except for her boobs, pussy, and butt cheeks.

She looks at the scene and says, "Well, well, well. I see you two could not wait for my arrival."

"Sorry, Mistress Trudy," came from their mouths as they drop to their knees.

"I see you slaves have learned some things but I see that you are truly in need of additional training."

"You know this conduct has consequences, don't you?"

"Yes Mistress Trudy," they respond.

"And what are those consequences?"

The black girl mumbles, "To be punished for bad behavior."

"Well at least you know that much. We might just as well get on with the punishment, don't you agree slaves?"

"Yes Mistress Trudy."

She then goes to a cabinet and takes out two dog collars and leashes.

She attaches the collars to the girl's necks and hooks the leashes to the collars. She then orders them to get on all fours like a dog. She goes behind each one and runs her finger up and down each girl's slit and then licks her fingers.

"You slaves have really been naughty; you are all wet."

At hearing, that I notice my shorts are very wet which makes me leak more.

"Well my slaves, let's go for a walk." She takes the leashes and leads them in a few circles around the room.

"It's time I think to begin your punishment and then some more training together."

We watch as some curtains open. We gasp. There is a black guy and a white guy in cages next to each other. The room is full of ropes, pulleys, tables, and crosses.

Mistress Trudy leads her two slaves over to the cages. As the slaves are approaching the cages, the guys start to get erections. She glares at them and says; "Did I tell you it was ok to get hard?"

"No Mistress Trudy," they say in unison.

"Well when I am finished punishing these slaves it will be your turn to be punished for having those nasty things up."

"Yes Mistress Trudy," they say again in unison.

"Get your asses back next to those cages and let them nasty dogs get a whiff of your heat, you bitches."

The black girl takes a position in front of the cage where the white guy is caged and the white girl goes to where the black guy is caged.

"You dogs sniff around and lick them bitches real good but do not get them to cum. If you do, your punishment will be doubly severe. Do you understand?"

She did not even wait for an answer.

As the males are doing their thing, the girls are pushing their pussies back further to get more tonguing.

I slip my hands into my panties and massage my clit seeing this.

I look around at my friends and they are already fingering their clits. Mistress Trudy is messing with things and then we hear,

"Imm...ccccuuuuuuummmmmmm...ooooooohhhhhhh!"

This is from the white slave as she collapses on the floor and shakes with her finger to her clit.

Mistress Trudy walks over to the black guy's cage and says, "Well, well, well."

Then we hear the same from the other slave girl.

"My-oh-my. I have four bad slaves that need punishment. I am going to be busy I see."

She takes the white girl and leads her to a wooden frame in the shape of a large X. Ok Jenny you-may stand. She takes off the leash and pushes her back to the X, raising one wrist up high and securing it with cuffs, then doing the same with the other wrist.

Then she spreads Jenny's legs and secures them to the X. The girl looks like an X and her pussy is so vulnerable. Jeez those breasts are so vulnerable too. I am getting more turned on.

"Ok, Kate, you slut and bitch, come!"

Mistress Trudy does the same with Kate, fastening her into an X form.

She walks back to Jenny, massages her breasts, and plays with the nipples until they appear to be rock hard. "You like that don't you Jenny?"

"No, Mistress I do not" is her reply.

"Good answer but your body deceives you," we hear.

Then Jenny lets out a scream. Trudy has placed a clamp on her right nip with a chain and weight. It is pulling her nip and tears are rolling down her cheeks.

As Trudy approaches Kate, we hear, "Please, Mistress Trudy, not me, please."

She screams as the same treatment is being applied to her. Her nips are already hard from seeing Jenny getting worked up.

Mistress Trudy then takes a riding crop and runs it up and down Jenny's slit. It has to be gliding over her clit because Jenny is trying to fuck it.

"Did I tell you to enjoy that Jenny?"

"No, Mistress Trudy."

Then another scream as the other nip is treated to the same treatment. Her nips are now both clamped with the chain and weight hanging down in front of her.

She walks over to Kate. Kate screams but this time it is a scream of pleasure.

When Trudy steps to the side, we see that Mistress Trudy is fucking Kate in the pussy with the crop handle.

She withdraws the crop, walks over to Jenny and asks her to clean it good as she inserts it into Jenny's mouth.

We hear the scream of pain as Kate's other nip is weighted up by Mistress Trudy after Jenny cleans the crop.

Trudy looks over at the guys and they are rock hard. She just smiles.

Trudy goes back to Kate and begins deep throating her and working a finger on her clit. When Kate is about ready to cum, Trudy breaks the contact.