Helping My Wife Pt. 02

In part 1, my wife and coworker were going on a weekend getaway to try and convince two potential wealthy clients to sign on with their law firm. If successful, my wife and co worker, Jessica, would each receive a $20,000 bonus. My wife was incredibly excited. She had been a bit down lately, and had really been looking forward to this trip. Her boss had even given her spending money to shop for some sexy outfits, and every night she would put on a fashion show for me and our 18 year old daughter, Brianna. A couple of weeks before the trip Jessica had to cancel. My wife was devastated knowing her boss would not let her go alone. Fortunately Jessica came up with a plan. It was a long shot, but it just might work. She said that since me and her were the same size, and I had some feminine features, and she also had gone shopping for new outfits, maybe with a little (or a lot) of help I could pass as a woman and be Jessica for the weekend.

Somehow my wife convinced me of this plan, and with the help of her, Brianna, and Jessica they managed to transform me into a sexy woman. I loved the way dressing as a woman made me feel, and it seemed to bring our family closer together. Besides learning to dress I also learned how to flirt with men. I guess the transformation brought out the sissy side in me. While I became closer to my wife, she no longer would have sex with me, wanting a real man to satisfy her sexual needs. So Brianna and Jessica thought my wife should have sex with a couple of young studs and teach me how to suck cock.

I even developed a crush on one of Brianna's friends, Jim, and they had me invite him over to our home. We made out for a while and then I gave him a juicy lipstick blowjob and tasted me first load of cum.

The night before our trip my wife thanked me for going along with this plan. She thought it brought the family together and thought I should dress up permanantly.

"We could go shopping together and pick up guys together, it will be wonderful."

Then she started talking about our business trip, giving me details of what I needed to know and say. "Basically, follow my lead, I'll give you a few legal phrases to know, but as long as you are wearing that hot lipstick I think we could seal the deal."

I said, "I will do my best, but I am worried about a few things, and I don't want to hurt your chances of getting that bonus."

"What is it that bothers you?"

"Well, it's one thing having an 19 year old boy here for an hour who thinks I'm cute and wants his cock sucked, but it's another thing spending a weekend with some men, making real conversation, and not slipping up."

"You'll do fine. We are sharing a room and I will be with you the whole time."

"What if these men want to have sex." I asked.

"I hope they want to have sex, I'm getting horny thinking about it."

"But what if they want to have sex with me?"

"Is that what you are worried about? I saw the way you sucked Jim's cock. You are a natural."

"Thanks for the compliment, but what if they want to fuck me? I've never been fucked and I'm scared that a big cock could hurt me."

My wife starts laughing. "Go in the bathroom and put on a fresh coat of lipstick. Meet me in the bedroom in 5 minutes."

I put on red lipstick and walk in the bedroom. My wife is standing there with an 8 inch strap on. "Beg for it Jessica, beg to suck this cock."

"Please let me suck that cock"

"You can do better than that!!"

"PLEASE, I want to suck your cock!"

"Crawl over here and start sucking."

I get on my knees and crawl over to my wife's cock. I am so excited I am ready to explode. I start licking, and sucking, making slurping noises. Everything my wife has taught me.

Then she says. "Get up and bend over the bed." I do as I am told. My wife pulls up my nightgown, pulls down my panties, and puts that strap on slowly up my ass. It hurts a bit at first, but as she starts fucking my ass faster and faster I get more and more turned on. As my wife keeps fucking me and screaming in my ear. "Take it slut, tell me how much you love getting fucked by a big cock."

"I love it." I screamed. Seconds later I came like I've never cum before and I collapse on the bed.

The next thing I remember is my wife waking me up in the morning telling me. " You need to get ready, the limo will be here in a couple of hours."

Then I ask her. "Did you fuck me in the ass last night, or was it a dream?"

"Yes I did, and you took it like a real slut."

"I guess that explains why I am a little sore. But what happens if one of the potential clients wants to fuck me and realizes I am not a real woman?"

"Believe me, you are a real woman. You worry too much, just like a little girl. Remember, I will be there the whole time, and my guess is if it goes that far any male is going to love your sissy ass."

While I was asleep my wife packed a suitcase and laid out my clothes for the day. We both wore conservative outfits, but I was told we had some sexy outfits for the evenings. I was still happy to be wearing matching panties and bra and stockings. As I applied my pink lipstick our daughter came into to check on us.

"You both look great, I have two such pretty mothers. Have a great weekend."

Almost at the same time my wife and I say. "No wild parties young lady." Brianna just smiled.

The limo pulled up at exactly 9 am for the four hour drive to our resort getaway. One thing about my wife's law firm, they spared no expense. The limo had a full bar and lots of snacks for the ride. As we relaxed in total comfort my wife showed me some papers and gave me a little heads up on the business aspect of the weekend.

Shortly before 1 we check into the resort. Our room is amazing, a luxury suite. It even has a little jacuzzi. A note on the bed said. "Don't forget your complimentary massage at 2 pm."

My wife and I can't stop smiling on how amazing the room is. Clearly we could never afford to stay in something this fancy. We take the elevator to the lobby and then walk to the spa. We are greeted by a very pretty receptionist Erica. She tells us that that our masseuses are Erin and and Alexis, the two best that we have. I must admit I am a bit nervous, but my wife calms me down and we strip to our panties and bra and we lie face down on the massage tables. Erin is working on me, and Alexis is massaging my wife. The women are making small talk. Alexis asks. "Have you women ever had massages before?" I say no, but my wife says,"I've had a few, I really love them."

Alexis asks. "What do you love about them?"

"They help me completely relax, and to be honest sometimes they make me horny."

"Wow that's interesting. Have you had male or femalle masseuses?"

"I've had both"

"Which did you like better?"

"Loved them both, sometimes you just need hands touching you in the right places."

"I will do my best." Alexis says. "So will I." adds Erin.

I immediately relax as Erin starts working on my shoulders. I turn my head to look at my wife. She smiles and blows me a kiss. Moments later Alexis's hands move from my wife's shoulders to her panties and I hear a little moan. Erin hands move to my ass. She compliments my panties and starts rubbing my butt. Then she says. "Ok girls time to turn over."

My wife turns over and takes off her bra. She sees a little panic in my face.

Alexis says. Come on Jessica turn over, we are all women here, we all have seen breasts."

I roll over and Alexis says. "I stand corrected, we are not all women. Jessica you sure fooled me. Unfortunately we have a policy at the resort and Erin will not allowed to massage you. We have another room where you need to go and have a male masseuse."

My wife speaks up. "He/She is my husband. It's a long story. Can she please stay in the room with me."

Erin says. "Ok, but we will have to bring John in to continue the massage."

While I wait for John, Alexis continues massaging by wife. She is feeling her breasts and I can tell from her moaning that my wife is loving it. Then Alexis says to me. "Jessica, is that an erection in your panties. Do you like watching me rub your wife's tits? Would you like to see me suck on them?"

Before I could answer John walks in. "What have we here?"

Alexis answers."This is Jessica."

"Hi Jessica, is that a gun in your panties or are you happy to see me?"

John is about 6 ft 2 inches in excellant shape. He has incredibly strong hands as he starts feeling me up over my bra. Meanwhile my wife and Alexis are making out and fingering each others pussies. My wife looks over at John and says. "I want some of that"

Alexis says. "Well, your firm did pay for the upgraded massage. Do want him to fuck you while you lick my pussy, or do want me to lick your pussy while you suck his cock?"

My wife says. "I can't decide, let my husband choose."

Next thing you know John is fucking my wife while she is licking Alexis's pussy, and my panties are soaked. Within minutes my wife and Alexis cum and shortly after that John cums in my wife's pussy.

An anouncement comes over the loud speaker that our massage session ends in 10 minutes. Alexis tells us to get dressed. John says. "Be a good sissy Jessica, lick my big load from your wife's pussy."

I do as I am told then my wife and I get dressed and go back to our room. My wife looks at me and says, "Why do you look so said dear."

"That massage experience was amazing, but I'm the only one who didn't cum."

"Don't worry honey, while we were getting dressed I got John and Alexis's phone number in case things don't work out with our dates tonight.. Speaking of tonight I think we should begin to get ready. I will pick out a nice sexy outfit. Let me know if you need help."

My wife picks out a short sexy dress for me to wear. This time it's a matching black bra and panties. A pair of sheer black stockings. My wife puts some soft plastic things in my bra to make it look like I have breasts. "They will feel like real tits if someone feels you up outside the bra." She suggests that we both wear red lipstick.

She wears a short cocktail dress and looks incredibly hot.

The restaurant at the resort is incredibly fancy. Two men sitting at the bar walk up to us and ask if we are Jessica and Amanda. They introduce themselves as Michael and Daniel.

Michael asks if we are sisters then says. "If every woman in your law firm looks like the two of you I think we can sign the papers right now."

My wife answers. "They are better looking than us, but we are more fun."

The maitre d shows us to our table and we order drinks and appetizers. While waiting for the drinks my wife starts talking business, explaining all the positive features of her law firm. "We have some of the brightest lawyers in the country. 80% graduated from ivy league law schools, and all the partners have been with the firm for over 10 years. I think we would be a perfect fit for the two of you. The food and drinks are coming, so I will stop talking business now."

"That's ok."Said Michael. "We did our homework and have heard great things. And I'm not only talking about the hot women. We will be signing the papers later, but in the meantime let's have a toast.

We lift our glasses and Daniel says. "Here's to a profitable partnership and to fun weekend at a magnificent resort with two beautiful women. We touch glasses and take a drink. We enjoy our appetizers and order more drinks. Michael says,"Jessica you are kind of quiet." I answer. "I'm kind of shy, plus I am enjoying listening to you and Daniel."

My wife chimes in. "Careful what you wish for, one more drink and Jessica won't shut up." We all share a laugh.

Michael asks if we were ever married and my wife answers. "I was married for 20 years then discovered my husband was gay."

Daniel says. "I can't believe you were married for 20 years, you look so young.

"Flattery will get you everywhere.'

"Do you have any children?"

"Yes, a have an 18 year old daughter."

"How did you find out your husband was gay?"

"Funny story, I was away for the weekend visiting family and my daughter was staying with friends. Well my daughter came home early and saw my husband dressed in woman's clothes and sucking the cock of one of her classmates."

"That's pretty hot, did you have a clue?"

"Some of my clothes were missing, but I just assumed it was my daughter wearing my clothes.. After confronting him I found a secret stash of panties and lipsticks."

Michael asks. "How about you Jessica. Have you ever been married."

"Sorry." I say, "I don't have a story that good. I've been dating Jim for a couple of years. He is really nice, a little on the boring side. I think it would be hot if he would wear panties once in awhile. How about you guys are you married?"

Michael say, "I've been married for 12 years, and we have an 8 year old son, but we have an open marriage and she's ok with me seeing other women."

"How about you Daniel."

"I was married for about 10 years, but I caught my wife cheating with my best friend."

By the 3rd drink I am pretty buzzed and I say. "Who wants to dance?". My wife agrees, but suggests we go to the ladies room. Kind of strange, I've never been in a ladies room. I say to my wife. "Nice story about how you found out I was gay."

"Yes, and nice story about wishing your boyfriend Jim would wear panties. Now let's freshen our lipstick, we have two hot guys waiting to dance with us."

We fix our lipstick and go back to the table. There's a band playing some slow music and the men walk us to the dance floor when my wife suggests. "Let's dance another time, why don't we take this party to our room."

In the elevator Michael starts kissing me while Daniel is kissing my wife and feeling her up. We get to the room and I ask my wife to go to the bathroom and help me fix my lipstick. I tell her my cock is about to explode. She has an idea. "Why don't you cum into this glass. You dick will calm down. Now hurry, we have cocks to suck."

I cum in the glass, fix my lipstick, and go greet Daniel and Michael. "Now where were we." I ask.

"We were making out." Said Michael, and he starts kissing me again. As our tongue met and he starts feeling me up I could hear my wife saying. "Wow, I've never seen a cock so big." I look over and my wife is licking up and down Daniel's cock.

Daniel says. "I am guessing you need a big cock after all those tears with a sissy husband."

"Yes I do, I need your big cock in my pussy."

"Beg for it slut"

"Yes, I am a slut for your cock. Please fuck me."

All this time Michael and I are enjoying the show. I am sitting in my bra and panties stroking his cock. A few minutes later my wife screams that she is cumming. Daniel pulls his cock out and cums on her chest. My wife struggles to sit up. She is trying to catch her breath when she says,"Now it's time for Michael and Jessica to entertain us. Michael, Jessica loves to get spanked before taking a cock in her ass. Leave her panties on and start smacking her ass."

Michael takes directions well. He puts me over his knee and lightly spanks my ass.

"You can smack her harder than that. C'mom she loves it, don't you Jessica."

"Yes I do, spank me harder."

Michael starts smacking my ass harder and faster. It hurts and feels good as the same time. Then he bends me over my bed, pulls down my panties and starts fucking my ass. Then, for the first time I feel a huge load of cum shooting up my ass.

My wife and Daniel applaud. Finally my wife, seeing that I am struggling to get to my feet, comes over, pulls up my panties and says. "We need to get to the ladies room and clean ourselves up."

We get to the bathroom clean the cum from each other and quickly fix our lipstick. My wife looks at me and says, "What a night, you were truly amazing. I don't know about you, but I have never been fucked so well. I am going to sleep like a baby."

Back in the room the men are getting dressed. They kiss us and say goodnight.

"We have an early morning tee time. We'll meet you for lunch. Bring the papers for us to sign. You women are amazing!"

Alone with my wife she hugs me and thanks me again.

i say,"No, I should be thanking you. By the way, why did you ask Michael to spank my ass."

"I thought it would be hot. A slut like you needs to be spanked once in awhile. I don't know about you, but Daniel and me loved watching it."

"My head is still spinning from feeling cum up my ass. Not sure how I feel about a spanking, but I don't think I will be able to sit for a week."

"i'm a little sore myself from Daniel's big cock, maybe the men will settle for blow jobs tomorrow. Let's get some sleep, it's been a busy day."

We both sleep late in the morning. Instead of going downstairs for breakfast. My wife asks me how I am feeling.

"To be honest my ass still hurts, and I have a tremendous headache."

"You were never a good drinker, but fortunately I have a cure for a hangover."

"Good, I'll try anything."

My wife walks over to the refrigerator. She opens it up and takes out a glass. "Nothing cures a hangover more than a cold glass of cum. Remember last night when we were in the bathroom and you jerked off? Drink up."

She hands me the glass and I drink it. "I hope this works."

"I have no idea if it works, I just wanted to see my sissy husband drink his own cum. I wish I took a picture."

After breakfast we just sit around the room relaxing and talking. Getting laid has definitely improved my wife's mood and kinkiness. She is constantly talking about cocks, or things to do with her new sissy slave husband as she now likes to call me.

An hour later Michael and Daniel call. They are coming back from golf and want to meet us for lunch in a couple of hours.

My wife smiles and picks out some outfits for lunch and we get dressed. We meet the men downstairs and walk to the restaurant. Michael holds my hand, and being a gentleman pulls out the chair for me to sit.

My wife laughs and says. "Not sure if Jessica can sit after the spanking you gave her." The men laugh, Daniel says," You girls tired us out so much that our golf game sucked."

My ass is still sore, but I am able to sit down. Michael says,"Before we order food, let's take care of business. Amanda, did you bring the papers to sign?"

My wife takes out the contract and the men sign.

"This calls for a toast." Michael says. We raise our glasses and my wife says. "To a contract almost as big as your cocks, here's to the beginning of a great partnership. What should we do tonight to celebrate?"

I say, "I don't know how we can top last night."

Daniel says. "I am sorry, but we have to get back home to take care of an emergency so we won't be able to party tonight. But how about you two hot women freshening your lipstick and giving us a blowjob for the road."

"We would love to", says my wife. "Hurry Jessica, let's fix our lipstick and take care of our new clients."

We go to the ladies room, fix our lipstick, and walk back to our table.

"Shall we go back to our room or yours?" I ask.

'Neither." Say Michael. "Get under the table."

So there we are under the table with two cocks staring at us. My wife whispers in my ear. "How about we have a contest. Whoever makes a cock come first wins, and the loser has to do whatever the winner says for the next 24 hours." Like an idiot I agree, after all,my wife has been sucking cocks for over 20 years, I've been doing it for less than a week."

"On your mark, get set, blow." The two of us start giving Daniel and Michael blowjobs. My wife is moving up and down Daniel's cock a mile a minute. Moments later she swallows a load of his cum. I am sucking on Michael's cock when he puts his hand under the table and forces his cock down my throat. As he cums I begin to gag and half the cum goes down my throat, the rest on my face.