Wife shares Husband with BFF

Chapter 2: Strapon

The first night my wife's friend, Zoey, stayed with us was an adventure I had never experienced. Led by my wife Jessie we talked about my love of panties, showed her me wearing panties and finally had a gigantic cum all over my wife's panties as Zoey cheered me on. For a conservative couple with a great sex life this was definitely new and adventurous. (See Chapter 1)

I woke the next morning, rolled over and cuddled my wife. I had a hard on she could feel poking her ass cheeks. I simply said, "Jessie, I love you so much. Thanks for last night."

Jessie said, "I loved last night as much as you. We are very private about our sex life and I really prefer it that way, but last night was so much fun and no harm was done to anyone with Zoey there to see everything."

I went to do my normal morning routine. I put on gym shorts and a T-shirt and went to the kitchen for a Monster drink. Jessie joined me and made coffee for her and Zoey. Not more than ten minutes later Zoey walked out of the guest room and Jessie offered her coffee.

We sat and talked. No one mentioned the night before. It seemed as though the three older, conservative friends were a little embarrassed to have had an enjoyable evening of panties and orgasm. Eventually, Jessie said, "I'm going to wash our matching panties on delicate. Is everyone willing to wear them tonight again?""

Zoey and I answered exactly at the same time, "I'm ready." The three of us had a good laugh and the conversation was right back to sexual issues just like the night before.

I said, "I'm heading for the shower. Is it safe to leave the two of you alone?"

Zoey said, "Well, we may be planning some fun for tonight. I doubt you will mind that."

I finished my shower and was drying off. Jessie came in and said, "Zoey asked me if you will wear panties all day and if she can pick which ones. Is that OK?"

I said, "Sure, I wasn't planning on wearing panties until tonight, but that's fine with me."

Rather than bring my panty box out to the living room, I wrapped the towel around me and said, "Jessie, tell Zoey to come in here."

Zoey walked in and took extra time looking at each pair of panties. She was really into this. She said, "I know you like the stretchy silk the best so I want you to wear this leopard pair with aqua lace trim on the waist."

I said, "You get your wish." I dropped the towel right in front of her and slipped on the panties in front of Zoey. My cock got hard as I put the panties on just like every time I put on panties.

Zoey said, "This may be a very good sign. You look so hot in panties. I had no clue how sexy it can be for a man to wear panties."

I went to our walk in closet to finish getting dressed. Jessie walked in and said, "Last night was so innocent. It was so comfortable knowing Zoey wouldn't try to have an affair with you or compromise our marriage. I really enjoyed the three of us having orgasms."

I agreed and said, "Zoey is so much fun, but honestly I am not attracted to her sexually. You satisfy me so much I can appreciate her without caring much about her sexually."

Jessie said. "I'm glad you said that. I have an idea for tonight. I want to ask you before I say anything to Zoey. In fact, if you agree I want to talk to her with you there."

I said, "Now what has your devilish mind thought up."

Jessie said, "Have you ever fantasized about a three way?"

I said, "Actually, I'm sure every man thinks about it, but you are more than I can handle and I love what you do to me. That's enough for me."

Then Jessie added, "Well, I've fantasized about giving you a day with me and another girl. I would never just do it, but after last night I think we can ask Zoey and it will be all good with no negative side effects."

I said, "My cock is for you, no one else."

Jessie said, "What if we told Zoey her job was to pleasure you and I let her wear my strapon. You love getting your ass fucked and now you can fuck me while she fucks you."

I said, "Now that's an idea I can eagerly agree to, but how does Zoey get some satisfaction?"

Jessie suggested I could lick, suck and finger Zoey, but not fuck her. She felt that should be fun for Zoey and thought she might even orgasm fucking my ass. Jessie said, "Let's go talk to Zoey. Let's not bring this up right away. Maybe we can work together and make her think tonight is her idea."

We walked out into our living room together. Zoey was just walking out of the guest bedroom. We talked about normal everyday things, but after a few minutes Zoey said, "Something Jason said yesterday has my mind spinning. Do you mind if I ask a personal question?"

Jessie and I agreed no conversation was off limits and Jessie said, "After last night I think we can talk about anything. Our friendship is stronger than ever before."

Zoey said, "Do you mind telling me every little detail about the day Jessie dressed Jason as a woman in Key West. The idea interests me so much. I'm getting wet just asking the question."

I started the conversation by saying, "Well that was an amazing day that I will never forget. When Jessie fulfills a fantasy not much is left to chance and the sex is over the top. What interests you the most?"

Zoey said, "Tell me about dressing as a woman and why you enjoyed it so much."

I replied, "I never thought about dressing as a woman. My fantasy was Jessie wearing a strapon and getting my ass fucked. It just so happens that Jessie never just does something. She is so dedicated to my sexual satisfaction that she took the idea and made it into a day rather than a sex act. Her planning and creativity made the sex better than anything I could have hoped for so when she had the plans so well organized and detailed I eagerly did my part."

Zoey was squirming in her seat. She was so fired up and wanted to know everything and all at the same time. I said, "Let's just relax at the pool and we can take the time to go over everything. Do you want to know about dressing up first or the strapon idea first?"

She wanted to know everything so we agreed to start at the beginning and save the sex for last just like that day.

I realized Zoey knew my wife and I well. She was in our wedding almost 30 years ago. In spite of that I told Zoey that the most important element of amazing sex in a marriage is communication.

About ten years ago I was in Asia away from Jessie for a month. We communicated by email and phone. Those conversations ended up being very sexual. I asked so many questions about what Jessie wanted when I got home. We talked constantly about what satisfied us the most. We came to the conclusion that if I focused on her sexual satisfaction before mine and she focused on my satisfaction before hers we would have a magical connection. We were right. Those thirty days of phone calls turned into regular texts, emails and conversations about sex. It never ends. The communication takes both of our sex lives to new peaks, but also improves every other aspect of life as well. We communicate so well nothing is out of our reach sexually.

On the other hand, without communication your sex life is limited to whatever happens when you are lucky to try to fuck your wife when she is interested. So the first way to get to wild and crazy sex is to ask your spouse what they like sexually. Understand their desires completely. Then ask about fantasies and talk about making them come true. Keep talking and learn everything you can. Things get so hot sex gets beyond anything you can dream about enjoying.

Zoey said, "Sounds good. Sometime this afternoon I'm going to call my husband and ask him what he wants the most sexually when I get home. After he answers I'm going to ask him if he has any sexual fantasies I can fulfill for him."

Zoey was learning and ready to take the first steps to unlimited pleasure.

The Zoey said, "OK, how did this dressing as a woman happen?"

I said, "Well Jessie introduced me to prostate massage on our first trip to Key West. We went to the adult store in Key West and bought a butt plug. I was so very nervous, but Jessie was very understanding and went very slow. I had more sexual pleasure getting my ass filled up than anyone can imagine."

Jessie was on the edge of her seat. She was getting into the story. Then she said, "I'm so fucking wet. Do you mind if I undress down to my panties and rub my clit once in a while."

Jessie said, "Enjoy yourself. After last night we are all very understanding of each other's pleasure."

I continued, "We got home and used the butt plug. It wasn't a regular thing. About once a month or so I asked Jessie to use it on me and it was amazing. It's a change of pace for me. I love getting on all fours and having Jessie use the butt plug to do my ass. It really feels good. Sometimes I leave it in and have her ride my cock cowgirl style. Whenever we use the butt plug the prostate massage produces massive cum loads."

Then I went on to add that one day I Googled Wife uses Strapon on Husband. I was watching this guy get fucked by his wife. It looked interesting. Jessie walked in and said, "What are you watching, porn?"

I said, "Yea, watch this. This wife is using a strapon on her husband"

Her reply was, "You want me to do that to you don't you?"

I said, "Well, I'm intrigued. It looks interesting, but the strapon is much bigger than our butt plug."

Jessie simply said, "Take me to Key West on vacation and I'll do it to you. Other than that, not until I get my trip to Key West."

We saved and planned. I had no idea what Jessie was planning. We talked about going on a three day trip and saving the strapon until the last day. We went and bought an eight inch black cock with balls and a harness that fit Jessie well. The cock seemed so big. She would not let me see, but in anticipation of the trip actually told me she was practicing her strokes and I was going to be very happy with her performance in the Keys. Again, I had no idea what plans she was making.

We arrived in the Keys and did our normal thing. We enjoyed Duval street. We went to sex shops. We bought clothes and got a henna tattoo each. Mine was the loyalty sign in Chinese above my cock. I shaved the area clean. Jessie's was a dolphin near her partially shaved pussy. She had her pussy hair in a Mohawk.

Finally the day came and Jessie asked if we could get back to the room extra early, right after lunch. I agreed and had no idea what was coming. Jessie always brings new panties and bras on trips. When we returned to the room I took a shower and walked out into the room. The bed had brand new sexy panties, bra, skirt and blouse displayed on the bed. I said, "Wow you have sexy things to wear tonight."

Her reply was, "These are not my things. They are all yours."

She explained that she had planned an evening with her as a man and me as a woman. This is not that big a deal in Key West. No one we knew would see us anyway so she suggested we role play. I wasn't sure at all. I'm not a cross dresser. I really wasn't comfortable. I said, "Are you sure? This seems a little weird."

She said, "Trust me. This is the place to play around with this kind of fantasy. I promise you will enjoy it and for sure not regret it."

I simply replied, "OK, I'm all in."

She told me to go shave my legs and clean up my nipples, balls and cock. After I did she followed me back to the shower and cleaned up my butt cheeks with an electric razor. My lower body and my nipples were baby soft and feeling very different. When I put on the panties, lace top stockings, pretty lace bra and then the skirt, blouse and wig I felt so good with no hair and my body covered in silk. I was quickly getting the idea that Jessie knew what she was doing.

Jessie sells Mary Kay so she did a beautiful make-up job on me. I do have to say my lips were very beautiful in a whorish red. Jessie was so into the fantasy that it turned me on a lot. The simple idea was Jessie was going to use a big black strapon cock on me, but she turned the entire day into a sexual adventure. I can say with all honesty that it is unlikely I will ever cross dress again, but if Jessie has another fantasy to fulfill I will be dressed like a woman any day anytime.

Jessie opened doors for me, pulled my chair out at dinner and basically every courtesy a man gives a woman. She even ordered my meal for me. She constantly whispered into my ear what she was going to do that night. Finally we walked home holding hands. When we arrived at the hotel she asked me to wait outside for a minute. I did as asked and my cock was rock hard with anticipation.

Jessie opened the door and had the strapon over her panties. That was it, just panties and strapon. She pulled me into the room and said, "Baby, I need to fuck you so bad. I have waited so long for this night. I'm going to treat you really good. I need my cock in you."

I dropped to my knees and licked and sucked her big black cock. She held the back of my head and thrusted her cock into my mouth. I held and stroked her panty covered ass as I sucked her cock. She said, "Oh baby, you suck cock so well."

Jessie pulled me up kissed me and said, "I have to have your nipples in my mouth, baby." She ripped my blouse off and then my pretty lace bra came off. She ravaged my nipples. At first she licked. Then she sucked. I was moaning and then she started biting my nipples. My moans became screams of pleasure. Jessie had her hand under my skirt on my cock in panties. I never felt so sexually excited. She took off the skirt. All I had left on was the lace top stockings and the panties Jessie gave me.

She said, "I know you want this cock as much as I want to fuck you, but I'm going to go slow and prime your ass. My cock is real thick and extra hard tonight for you. I plan to leave your panties on all night and your stockings too. I want to feel your stocking covered legs around my head as I fuck you."

I got on my back on the bed. Jessie pulled my panties to the side and teased my ass hole. I was going crazy. It felt so good. She lubed my ass hole. She put one finger in me, then two and then three. I could feel my ass relax. Jessie said, "I think you are ready baby. I'll go slow so you can enjoy every second."

She put my legs over her shoulders. She placed the big black cock at the opening of my ass. She moved it up and down to tease me. I said, "I want cock baby. Give it to me. Give it all to me. I want to feel your balls against my ass cheeks.

She put in the head and it went in easily. She asked if I was OK. All I said was, "I love you baby, fuck me. Fuck me please."

She slowly buried her cock into me. I moaned with pleasure. She stroked my ass in rhythm. First she used two or three real slow strokes followed by two real fast strokes. I screamed, "Give it to me baby. Fuck me hard."

She pounded me real hard for a lot of strokes. I was gasping for air. I said, "More baby, more."

She pulled out of me and said, "Stand up so I can give your ass a good work out." I stood up and bent over the bed. Jessie pulled my panties aside and put her cock in me again. This time she held my hips and pulled my ass to her as she pushed forward. I could hear and feel her skin slapping my panty covered ass. She slowed down and spanked my ass, one side then the other. At first the spanks were light and then hard. I loved it.

Finally Jessie said, "How do you want to cum baby?"

I said, "Put me on my back and tease my pleasure spot until I cum." Many female pleasure experts call the man's frenulum the male version of a clitoris. Jessie was using my version of the clit to give me an orgasm while she fucked me

I had one of the largest cum loads of my life. It shot all over my chest and stomach. Jessie licked some of it off and kissed me so I could taste my cum. I said, "Feed me more love juice."

She used her fingers to scrape up the cum and put it in my mouth.

That was a wild and very, very enjoyable day.

By now Zoey was on fire rubbing her own clit. She said, "What a story! I am so jealous."

Jessie signaled to me to leave for a second without Zoey seeing her do it. While I pretend to be in the bathroom Jessie said to Zoey, "I have another fantasy and I think you are the perfect person to help me bring it to life."

Zoey said, "I'm all ears with a really wet pussy."

Jessie whispered, "I've always wanted to give Jason a night with two ladies working him into sexual ecstasy. After last night I know Jason trusts you. How about you and me double team Jason tonight? You wear my strapon and I'll do everything I can to compliment that. For sure, I want Jason to fuck me from behind standing up while you fuck him from behind at the same time."

Zoey said, "Oh my gosh, I just died and went to heaven. Can ask one question?"

I said, "Sure, what is it?

She eagerly said, "Is there any way Jason could dress as a woman for a while. Could we make this night, maybe just for a portion of the time, three woman all over each other?"

Jessie thought it sounded like a good idea, but told Zoey to stay quiet for a while so we can work our way into the conversation.

Jason returned and Zoey said, "Jason, that is one of the most erotic stories I have ever heard. I might not believe it if it wasn't about you and Jessie."

Jason said, "Anything is possible if you love each other enough to communicate what you want."

Zoey blurted out, "Well how is this for communication. I want to fuck you tonight."

Jason looked at Jessie and said, "Honey, I want what you want. If this is the best way for the three of us to end a very special weekend then you set the ground rules and I'll do my part."

Jessie said, "Well I never expected this, but I do have another fantasy I'd love to fulfill. How about if you dress up in lingerie, your wig and make-up for Zoey tonight and the two of us try to give you more pleasure than you can handle?"

The Jessie added the ground rules that Jason only fucks her. Zoey can have a dildo, tongue or fingers, but not Jason's cock. Other than that anything goes.

Zoey jumped up and said, "My panties have been soaked since Jason started his story. Can I pick out Jason's lingerie for tonight?"

Jessie and I walked to the kitchen while Zoey played with herself to the last orgasm until later that evening. Jessie said, "I told you she would think it was her idea. Good job. Now let's make this a night to remember just like Key West."

A few minutes later Zoey walked into the kitchen looking relaxed and satisfied, if only temporarily. She said, "Jason and Jessie, I realize I'm just the guest in this house where fantasies come true, but I have a couple of suggest as the new lady in the group."

Jessie said, "I knew you would get into this in a big way, really fast. Just remember this all starts with communication with your husband and asking what sexual things he enjoys and wants. You need to call him in a few minutes. Before you call your husband go ahead and make your suggestion."

Zoey said, "You are right. I am excited to make a sexual phone call to my hubby. My suggestion is that we have a group shave before the activities start. I'd also like to paint Jason's fingernails. What do you think?"

Jason replied, "I love the idea. I want my entire body shaved below the waist to enjoy the feeling in lace stop stockings and panties. Anything else you want me to wear just give it to me. I'm happy to make everyone else happy, but for sure a smooth ass will make both Zoey and me happy."

Jessie added, "Zoey you shave Jason's nipples and ass. I'll shave his cock and balls. He can do his own legs. Do a good job on his ass because you will be fucking it. Just a suggestion, be gentle getting started, but feel free to wear his ass out once he is comfortable. He loves a good hard ass fucking."