A Little Help For A Friend Pt 02

If you read my story,

A Little Help for a Friend

, you realize my wife and I used a three way to help a friend get back to having sex again after a tragedy. That friend, Julie, wanted to take us to Key West on a wild sexual adventure. All I needed to do was two expensive bikes for her; one a very expensive carbon fiber triathlon bike and the other nice road bike. Well, I sold them for $5,650 and handed her the money one Saturday afternoon. She grabbed me and said, "Thanks so much for selling the bikes. Now get ready for some wild and crazy sex in Key West big boy. I plan to give that ass and cock of yours a workout."

I thought to myself, "Wow, this lady needs a regular cock in her life."

I went home and Julie had already called my wife Jessie. She said she had a friend with a small plane. She had made arrangements already for him to fly us to Key West. All he wanted was fuel costs. She said she would pay the fuel costs and give us the date as soon as she could make the hotel arrangements.

Jessie was all fired up. The agreement was I would dress as a woman in Key West and Julie would dress as a man. Jessie planned to dress in her normal sexy way. This was destined to be an epic sex weekend.

As the weekend approached my wife said, "I have a request for our Key West weekend."

I said, "Tell me. This has to be interesting. All of your suggestions are wildly sexual."

Jessie said, "I want you to get a Brazilian Dare to Bare All waxing."

I said, "I'm happy to do so. I will make my dressing as a woman on the trip much easier and make my nipples, balls and cock much more sensitive."

Jessie said, "Great. I'll make the reservation and go with you. I'm going to be all over you when you are hairless and Julie will love fucking your ass after a waxing."

I got waxed. It isn't pain free so Jessie had to give me a couple days to recover. Once I was recovered I got a real treat, an all-night fuck with pleasure. Every inch of my hairless body was licked, sucked and kissed.

We prepared for the trip to Key West with a unique passion. I had one set of women's clothes that Jessie bought me for our own Key West trip. I had plenty of panties already. Jessie took me shopping and we got a long, ankle length stretchy skirt that was real tight on my ass, a spaghetti strap top and ladies flats to wear one night. I now had two sets of ladies clothes, one for Friday and one for Saturday.

Julie called Jessie and told her she had shopped at several consignment shops and had two pairs of men's slacks two shirts and a sports coat. She was fired up and ready. She planned for all of us to wear matching panties both nights and told Jessie she would give us our panties in Key West. Finally, the day arrived and we drove to Julie's house to pick her up. Our plane and pilot was at a little airport. We could park and leave our car, no security, no long lines, no waiting.

We boarded the four seat plane for the short hour ride to Key West. We were staying on Duval in the heart of the action. We arrived, grabbed a cab and were in our room by 2PM. It was Thursday afternoon. We planned a relaxing evening to talk about the plans for Friday and Saturday followed by a fun three-way that evening.

We left our room around 5PM to go to Sloppy Joe's before dinner at sunset. Julie was really into the weekend. Her enthusiasm had Jessie and I fired up as well.

After we had a few drinks, we decided to eat light and watch the sunset around 8:35. After we ordered Julie wanted to get deeply into a discussion of the next two nights. She indicated she had done some research. She wanted to check out a couple places that cater to the cross dressing lifestyle. We agreed that was fine. Jessie and I thought it would be a lot of fun.

Julie said, "Great, you guys are so much fun. I hope we can have some relaxing three way fun tonight and get into the real reason for the trip on Friday and Saturday."

I said to Julie, "Jessie has fucked me every day for a week. When I get fucked that much I can go a very, very long time without the desire to cum. I have to actually work on cumming to blow my wad. That's a good thing for you and Jessie."

Our food was served. We ate and Julie put the address of the cross dressing bar into her iPhone. She said the bar was a few blocks off of Duval. It wasn't hard to find.

We walked into the bar. It was as normal as any bar in Key West. We sat at a table and the waitress came to serve us. We ordered drinks. When the waitress served our drinks Julie said, "I was wondering if you could tell me something about your bar. Some research I did said it was a cross dressing bar. Is that true?"

The waitress said, "You are right. I'll let you try to figure out who is cross dressing. Good luck and come back dressed as the opposite sex."

Julie said, "We'll be here tomorrow dressed very differently."

Julie was excited. She kept asking us what we thought about a certain person. One girl in a tight mini skirt had a slight bulge at the crotch. One guy seemed to have very smooth facial skin. Honestly, it was hard to determine anything.

We had a drink and Jessie said, "This place is for tomorrow. I'm ready to eat some pussy, suck some cock and fuck. How about you two?"

Julie said, "Let's go relax and have some pleasure."

As we walked to our hotel room, Jessie told Julie I had a Brazilian wax. She wanted to see everything and said, "It will be fun to fuck your smooth ass, Jason."

I said, "You are welcome to fuck me anytime. That's the purpose of this weekend. We all get fucked and fucked a lot."

We arrived at the room. Julie passed out matching silk leopard panties with black lace trim. She said, "Jason, let me help you slip yours on. I want to get a good look at your smooth hairless cock, balls and ass."

I replied, "I'd love your help. I'm hard already. I took a Viagra back at the bar and am ready for a long night."

Julie played with me everywhere. She felts my balls, cock and paid special attention to my ass. She said she wanted to save my ass until tomorrow when I dressed as her girlfriend. After she played with my ass, I turned around and said, "I want your pussy juice in my mouth. Get on your back on the bed."

She laid on her back. I used my hand to massage her pussy mound. I then pulled on her pussy lips and rubbed both pussy lips between my thumb and forefinger. Her pussy was shaved and so soft. I put a finger in her and massaged her G spot. Finally, I licked, kissed and sucked on her pussy lips. I saved her clit for last sucking on it and moving it in and out between my lips. Jessie jumped in and played with Julie's tits while she kissed her. It wasn't long and Julie was moaning. The moans turned to screams and she had a very strong orgasm. She said, "I have more. Please don't stop. I want more."

I kept eating her pussy, but Jessie sat on her face to give her a pussy to lick. She had two more strong orgasms and the night was getting hot. I said, "Now it's your turn Jessie. I want your pussy nectar."

Jessie replaced Julie on the bed. I used the same techniques on Jessie. I know she loves my mouth and tongue. To my surprise Julie got one her back and positioned herself between my legs as I was kneeling to eat Jessie. Julie started sucking and licking my balls. Then she moved to my cock and deep throated me. It was very hard to concentrate, but I did get Jessie off twice. She was ready and had her orgasms quickly.

I got on my back on the bed and the girls went to work on me. Jessie worked my nipples. Julie kept sucking my cock. I enjoyed the pleasure, but didn't want to cum so I said, "Who wants my cock in their pussy?"

In unison, both Julie and Jessie said, "Me."

They laughed and Julie told Jessie to go first. I got Jessie on all fours and gave her a good pounding. While I did that, Julie kneeled in front of Jessie so her pussy was right in front of Jessie's face. Jessie said, "Lay down in front of me so I can get eat you better."

Julie did as asked. It seemed like a miracle, but both Jessie and Julie had an orgasm at the same time. Jessie fell to the floor and said, "Your turn Julie for Jason's cock."

Julie got up and the bed on her side and I got on my knees behind her straddling her bottom leg. I can get real deep this way and fuck real well for a long time. Julie said, "You cock is so deep in me. I love this. Give me that cock, big boy."

I kept fucking Julie. Jessie was still resting. Then I heard Jessie say, "Give her a big cum load, baby. Fuck Julie hard and explode a big wad of your beautiful cum in her."

After Jessie said that I picked up the speed. My thrusting got faster and faster. Julie screamed out, "Fuck me. Fuck me hard. I want you to pound my pussy. I want your cum. Give it all to me."

I had a big load and was done for the evening. We all agreed that the night was a lot of pleasure, but just the first of three. Julie said, "I can't wait until tomorrow when we all cross dress and fuck like animals."

We got a good night's rest. I woke up to Julie and Jessie playing with my cock. I said, "That feels great girls, but let's let my cock rest until tonight."

We went out to breakfast and headed to the beach. During the afternoon we visited the adult store and a leather store. We had plenty of toys with us, but the girls wanted to buy a dildo bigger than what each of them already own so they bought a new dildo and a video on strap-on sex.

As we prepared for the evening the girls wanted to dress me and work on my make-up. I agreed and they had a fun time doing a make-over on me. When it was time to get dressed they added to the perfect make-up with a blonde curly wig. They enjoyed slipping my silky white panties over my cock and adding a garter belt with white lace top stockings. The bra was new. Jessie had purchased a sheer bra and DD breast forms. I now had big titties and nipples that were very obvious in the sheer bra. The girls added the short skirt and see through white blouse. My nipples were visible through the blouse under the right conditions. I have to say I looked very sexy. The girls did and amazing job cross dressing me. I had massive DD tits and beautiful nipples.

We went to dinner at an outdoor café. Julie asked what we wanted and also asked if she could order for us. We agreed. The waitress arrived and Julie said, "My two ladies will have a Napa Valley salad with the dressing on the side and I'll have a Caesar salad. The waitress said, "Thank you. You are lucky to have two such beautiful ladies."

The waitress put her hand on my shoulder and said, "Your blouse is very, very impressive."

I was getting into this for sure.

We ate our meal and headed to the cross dressing bar. We fit in perfectly. It was hard to tell what gender anyone was given the fact the ladies could be men cross dressing. Julie went to the restroom. She came back with a gigantic smile on her face.

She said, "The restrooms are unisex. That's a good thing. I opened the door to the restroom and some cross dressing guy had his skirt up getting his massive cock sucked by someone dressed as a man or maybe it was a man. I can't be sure which, but that guy's cock was bigger than any I've ever seen in person. He looked like a porn star."

Then the waitress came over. She said, "I over-heard your conversation. We also have a private part to our bar. There is a cover charge and you have to sign a disclaimer that any and all sex is consensual and not purchased."

Julie said, "Take us there."

I immediately commented, "Girls, HIV/AIDS is a real thing. Let's look, but not touch. We have each other. Let's not take any risks."

We all agreed.

As we walked into the room, all three of us saw the guy dressed as a woman with a big cock. He had the guy who was giving him a blow job bent over a table and was fucking his ass.

I said, "This is interesting."

Then I said, "I think I'm going to take my blouse off. You two can enjoy the view and do anything you want."

There I was cross dressed as a woman with DD tits showing for the world to see. I was getting lots of looks. One lady or person dressed as a lady came over and said, "Can I play with your big titties."

I said, "Sorry, I belong to this couple. I'm their sex slave."

I looked at Julie and Jessie and they were kissing and rubbing each other's crotches. I said, "Hey you two. Don't you want some of these big tits?"

They each took a tit and started playing. I felt like a real woman and liked it, but I was still a man with a hard cock and wanted pussy. Then I said to the girls, "I'm going to take my skirt off. One of you suck my cock."

Julie said, "I want to suck you off. I need a cock in my mouth."

How crazy was this. I was dressed as a woman with real looking DD tits, no blouse and no skirt, only panties and a bra getting a blow job in a private bar. Honestly, it was very, very exciting. I was fired up to get back to the room and go wild.

A man dressed as a woman approached the three of us. He pulled his skirt up and got his cock out of his panties. He said, "Would one of you three enjoy sucking this?"

I looked over and saw the longest, thickest cock I had ever seen. I said, "Sorry, but we are not going outside our threesome tonight."

I pulled Julie up to me off her knees and said to her and Julie, "Let's get back to the room. I am so ready to fuck the two of you. Can you believe the size of that cock?"

Julie said, "We can't get to the room fast enough. That cock makes me want to fuck right now."

Julie helped put my wet cock back in my panties and put my skirt back on while Jessie helped with my blouse as she kissed me.

As we walked to the room the three of us walked holding hands. I was in the middle. Several times Julie and Jessie dropped my hand and rubbed my ass. It felt really good. My response as they rubbed my ass was, "I need a cock in me so bad. I hope the two of you don't mind putting on the strap-on and giving me some good cock."

Julie said, "Slow down baby. You'll get plenty of cock tonight. Let's make this night last until sun rise. That's lots of fucking for all of us."

I said, "Please don't make me wait, baby. I need cock now."

When we arrived at our room both girls started kissing me and undressing me. Jessie got her strap-on on first and laid down on the bed. She said, "Ride this cock until Julie is ready."

I lubed Jessie's cock real well and straddled her. I reached behind myself and placed the cock at my ass hole. It was tight, but I was able to relax and take it all. I was bouncing on the cock and writhing back and forth. It felt so good. I had my hands on Jessie's big tits and she had her hands on my DD tits. Jessie said, "You seem to be having a very enjoyable time riding me. You are wild."

I replied, "I am so eager to get my ass fucked, more than ever before. I love this night."

Finally, Julie said to me. "Do you want some of this new bigger cock? Are you ready for some of this?"

I said, "Give it to me baby."

I rolled off of Jessie and stuck my ass in the air. As I did Julie was stroking the new bigger cock with plenty of lube. She mounted me on all fours and the bigger cock slid into me. It felt good. I said, "Give me your cock baby. Pound me. Pound me hard."

Julie was careful, but was thrusting aggressively. Finally, my ass had enough. I wanted to start fucking. At the same time, Jessie said, "I really need Jason's cock in me."

Julie said, "It's all yours baby. Roll over onto your back Jason. Jessie you ride him while I fuck him."

This was a first for me. I had never had Jessie ride me while another girl fucked me. I was great.

The next thing I heard was Julie saying, "I need my pussy and ass fucked together. I am so ready to get pounded. I need cock so bad."

I got on the edge of the bed and Julie mounted my cock. She was crazy wild. Jessie approached her from behind and asked her to calm down so she could get the new bigger cock in her ass. She got it in and Julie was screaming and thrusting her ass back towards Jessie. She slowed down a bit and started rubbing her clit and had multiple orgasms.

Jessie said, "Let's relax and have a glass of wine. Can you handle a slight break Jason?"

I'd love to cum, but I can stay hard until you ladies are ready."

We had a glass of Chardonnay. The girls discussed what other sex they wanted. I simply said they could use me all they wanted, but in the end I wanted to doggie fuck Jessie until I had a big cum.

While we were still having the wine Jessie started licking Julie all over. Julie returned the favor. Within seconds they were on the bed going after each other with screaming orgasm after screaming orgasm. I sat in a chair enjoying the show and slowly stroking my cock. The girls finally looked up. Julie said, "Time for you big boy. I love that thick cock of yours so much."

Jessie said, "We are going to ravish your body licking your nipples, balls, cock and ass. Sit back and enjoy the double team."

I was in heaven with pleasure. Finally, Jessie got on her hands and knees and tapped her ass. She said, "This is all yours Jason. Please fuck me hard and give me your cum. I need your cum. I want your cum."

I mounted Jessie and started slow, but it wasn't long and I was thrusting hard. I usually can control my cum, but it had been a long night with a stiff dick and I really wanted to cum. I could feel the cum building. I said, "I'm going to cum Jessie. I love you. I want to fill your pussy with my cum."

She said, "Give it to me baby. Fuck me and cum in me."

My reply was, "Jessie, Jessie, Jessie - I love fucking you. Oh fuck. Oh Jessie. I'm cumming. I'm cumming."

Julie said, "It's about tem minutes to sunrise. Want to go watch the sun come up before we go to sleep?"

We quickly dressed and walked to the beach. The sun was rising on a new day. What a night of adventure and sex! I needed sleep for the next and last night. What an experience!

We slept until after 12 noon. We showered and went to lunch. The conversation was about the cross dressing bar. I said how exciting and energizing it was to have my blouse off, even though I am a man and how great it was to get a blow job in public with everyone seeing my panties. It was crazy, but exciting. I had never let anyone see me in panties except the rare three ways Jessie organized.

Julie said she knows we are conservative at home and our three ways are designed to spice up our marital sex. She said she could feel the loyalty between us. She also said that she wanted to jump right into some wild sex at the cross dresser bar.

Jessie added that we've had very few three ways and only once had a three way with someone from our local community. We have no idea where that girl is now. We are very loyal to each other and want our marriage to be the best ever. Anything we do is for each other.

I expressed my concern that sexually transmitted diseases were real. I emphasized that I used to tell my high school students that went you have sex with someone you also are having sex with everyone they've ever had sex with so it can be very dangerous and unhealthy.

Julie said she understood, but the raw sexual energy was so exciting.

As the evening approached Julie had an idea. She wanted to wear her strap-on under her skirt and for Jessie to do the same. She wanted the three of us to flash the crowd in the cross dresser private bar. We agreed. The girls wore panties, then the strap on and then another pair of panties to attempt to hold the strap on cock down.

Julie asked me to carry a purse with me like any woman would. I didn't see any reason not to carry a purse.

We went to dinner and then the bar. We had a drink in the public area and then approached the private area. We walked in and moved to the couches and cocktail tables. The bar was a little more crowded and it had a lot of sexy looking men and woman. I had no idea which gender anybody was.