My Fantasy Weekend Ch 01

Writers Note: I want to thank everyone for the fantastic support and emails you sent me on my first story series, "Spanking Kenny's Wife". I encourage you to send me your thoughts and comments on this series, too.

After a huge fight with my wife 2 years ago, we spent a whole weekend making up. This turned out to be just about the best weekend of our marriage, so far. During that weekend, we spent the majority of our time having wild sex, talking about sex and exploring new dimensions in our sex life. One night, I asked Julie to tell me her deepest and most secret fantasies. While we lay together that night, I listened silently as she told me all about her secret sexual wishes. I was spellbound as she spoke, having no idea she had these kinds of thoughts. Thoughts about having multiple partners at the same time, being dominant over a submissive male or female, and other things that I had never head of from her. The descriptions were graphic, vivid and intensely sexual. I knew she wasn't making this stuff up because it was too well thought out - as if she had played it over and over in her mind a hundred times. Julie is not the kind of woman to use blatantly obvious sex words like 'cock' and 'fuck' very often. Just hearing her use those word so often, especially referring to her fantasy about sucking and fucking a 'monster size cock', quite honestly, turned me on immensely. Once she was done, we fucked like rabbits and settled into a nice cuddle with me spooning behind her. As we were resting, Julie asked me to share my deepest and darkest fantasies, too, which I did.

As a direct result of that weekend, I secretly arranged for her to live out two of her fantasies. I painstakingly facilitated every detail to ensure she would be safe in every way and everything would unfold for her exactly the way she described it to me. Over the course of the next six months, I gave her two fantastic weekends where she got the permission and opportunity to fully experience her dreams. I told her she was free to totally enjoy and live her fantasies out with no repercussions what so ever. Needless to say, her fantasy weekends were a complete success and I enjoyed watching her go through it. She was completely surprised, overwhelmed, gratified, overjoyed and very appreciative. She repeatedly thanked me over and over again. Our relationship became stronger, we became closer and the boundaries of our sex life widened considerably. I've never regretted it or second guessed my decisions to allow it. And, I've never been worried that I opened Pandora's Box for trouble down the road.

But, this is not the story of Julie's fantasies (I'll write about that in my next series of stories). Why then, you might ask, would I take the time to give you all that information? The answer is that this is a story of how she reciprocated and facilitated my fantasies into my own fantasy weekend.

I honestly can't put my finger on a point in time when Julie started to work on my fantasy weekend. She's a corporate project manager, and as such, she's a detailed planner and knows how to get things done. There were absolutely no outward signs of what she was up to. Sure, I can remember bits and pieces of conversations, fantasies and confessions we shared, such as my life long interest in panties, my interests in playing a submissive role and fantasies concerning exhibitionism and humiliation. I clearly remember how we told each other about our bi-curious interests. But at the time of these discussions, I never pieced anything together or thought much about it beyond our new sexual openness. Truthfully, Julie seemed to have nothing more than a sincere interest in exploring what turned me on. Or, so I thought.

Last year, she 'matter-of-factly' asked me if I would be willing to put myself completely in her hands so she could give me a fantasy weekend 'I would never forget'. Not wanting to let that question go without more details, I tried every thing I knew to get more information from her. However, Julie wasn't saying anything more than she already had. She simply wanted an answer to her question. She stood firm saying "You'll just have to trust me."

Unfortunately, I'm not the kind of person that can make a blind commitment without knowing what I'm getting myself into. She proudly reminded me how she was able to trust me without question when I set up her fantasies and asked "Why can't you trust me, too?" She had a point, so not wanting to hurt her feelings, I told her "Sure, Babe, if you asked me to do that, I would."

"I'm not kidding here," she said, "If I decide to do this, you'll have to promise me right now that when and if the time ever comes, you'll just go with the flow, do whatever I say and not ask any questions. Are you okay with that?"

"Well, yeah, maybe. It depends on what you have in mind. I'm not going to let you cut my nuts off, pierce my pecker or something like that. Jeez." I replied.

Julie laughed. "I wouldn't cut your nuts off, Honey. I love them way too much for that. But, I mean what I'm saying. If you agree, there's not going to be any changing your mind or backing out. You would have to do exactly what I tell you to do without any argument and do so willingly and happily. If you do, I give you my word that you'll be safe and have just as good of a time as I had on my fantasy weekends. Plus, there will be a special reward waiting for you when it's all over."

"What kind of reward?" I asked.

"A special reward. Something you mentioned a long long time ago when we were dating," she continued, "and you've never brought it up since."

"Do you swear to me you won't make me do anything I don't want to do?" I asked.

"Yep, you have my word on it. So, are you in or out?" A smile formed at her lips as she waited for my answer. I told her I was 'in' and that I would agree to what ever she said. She kissed me and told me I wouldn't regret it.

I immediately started snooping around, looking for signs or preparation or evidence of any plan she was cooking up. Unfortunately, there was none to be found. Actually, I should re-phrase that – I should say 'I wasn't observant enough to see the signs'. In looking back, the signs were all around me.

For example, one of the signs of her preparations I missed were our visits to an adult novelty store every few weeks. She had never shown any interest in going there before, but, we were now going there about twice a month. While there, we would always buy some sex toys to spice things up a bit. While browsing during one of our early visits, she picked up a black leather strap-on dildo harness - the kind a Dominatrix would wear. I looked at her and raised my eyebrows sharply. "Come on," she said, "you know how much you like having something in your butt. This might be fun. Go ahead, just tell me you've never thought about it...." It was true, I do like it when she puts her fingers or a small toy in my ass. We both enjoy that kind of thing and routinely took pleasure in some kind of anal play. Seeing that she was excited about the possibilities, and being more than a little excited about it myself, I was all for it. She selected an average size dildo to use with the harness and we left the store with our new toys.

After returning home, we made dinner together and conversed about all the different toys at the store and the strap-on we purchased. I could tell that she was eager to get dinner out of the way so we could play. She even made some comments about trying out the strap-on tonight. Personally, I was starting to have second thoughts about the strap-on and was hoping she might just want to fuck normally and forget about the strap-on for now.

When dinner was over, we cleaned up and she took my hand and led me upstairs. We took a long hot shower where she washed my hair and my body, teased my cock by washing it until it was painfully hard and poked her soapy finger up my butt. She could tell I was preoccupied with something and asked what it was.

Holding her in the shower, with my erection held tightly between our bodies and with the hot water streaming down on top of us I got deadly serious. "Okay," I started, "Having your fingers in me, or the vibrator in my butt is a little different than having a dildo in there."

"You think so?" she asked.

"Well, sure." I answered.

"Honey, I don't think that's what's bothering you at all," she said, "You've never blinked an eye when we've played back there. What's really going on?" I just looked at her not knowing how to respond to that.

"How many times have I had my fingers or our vibrator in you, Sweetie? Do you have any idea?" she asked.

"A lot, more than I can count, I guess." I said.

"And did you enjoy it," she said, "I mean, did it turn you on and help you cum?"

"Julie, you know the answer to that." I said, "I love it when you do it to me."

"So, let me see if I have this right..... when you lay on your back and raise your knees up so I can play with your butt with my fingers or the vibrator... that's somehow different than doing the same thing with a dildo?"

I couldn't think of a good answer, but, it didn't matter because what she said next totally pinned it for me.

"Here's what I think," she said, "You're freaked out because the dildo looks like a real cock. It has a head like a cock and balls like a cock. It has those veins down the side. That harness thing holds the dildo at the same place where a man's cock would be. Not only that, but, to use it, I would have to fuck you just like a man would fuck. Is any of that close?"

You know, I really hate it when she does this. She's a master at using logic and reasoning and knows me all too well. "I just don't want you to get the wrong impression." I said.

She kissed me and cradled my head in her hands and said "Honey, I think you're afraid you might enjoy it this way and embarrassed that I might know you enjoyed it."

I was silent again as I searched my feelings.

"Am I wrong?" she asked.

I shook my head. No, she wasn't wrong. She hit the nail right on the head.

"Listen," she said, "Our sex life is great. The reason it's great is because we're truthful with one another and have confidence that neither one of us would ever say or do anything to hurt the other one. I know you really like having something in your butt. Guess what – so do I. I also know that you really get off on it when I fuck your butt with our vibrator. I see the way you react every time I do it to you. You love it - I know you do. So what's the big deal using the dildo instead of my fingers or our vibrator? You already told me you had some bi-curious fantasies. Wouldn't you rather try this with me, in the safety of our own bedroom, to see if it's what you think it is? If you don't like it, we can put it away and no harm done – we can say we tried it and we didn't like it. I actually thought you would be thrilled about trying this."

"I am, I mean I was, but...." She put her fingers up against my mouth to stop me from talking.

"Honey," she said, "Let me tell you something. When you fuck me back there I get the most incredible feeling of submission and love for you. I'm offering you the most private part of my body, and letting you fuck me there. When you're in me back there, the feeling I get is more than sexual – it's cerebral. I'm submitting to one of the biggest social taboos there is, all for the man I love."

She looked into my eyes and then kissed me. "For you, though," she continued, "it could be even better. The pressure of the dildo on your prostate might give you the most intense feeling you've ever had. And I know you crave that feeling, so don't deny it. Whenever I touch you there, I can feel that little gland get hard just before you cum. I want you to experience the way I feel when you fuck me like that and I want you to have the chance to see if you like this. If you don't like it, we'll never do it again. You know as well as I do that you're always going to wonder about it."

All I could do at that point was kiss her. So, with the water running down us, we kissed passionately until she broke the kiss and looked at me.

"Okay," I said, "You're right, I do want to try it." And I was being truthful with her, too. In just a few moments of time, she had completely verbalized and resolved my hesitation. Damn her.

We finished our shower and she dried me off. I didn't say much, embarrassed by the fact that we both knew she was going to fuck me in my ass just the way a man would fuck a woman, or, more exactly to the point, the way a man would fuck another man. Embarrassed or not, my cock betrayed my embarrassment and became longer and harder than it was in the shower when she was playing with me.

When we were done in the bathroom, she took me by the hand and led me to the bed. She grabbed both bed pillows and laid them on top of one another and guided me into a position on my hands and knees with the pillows under my stomach. This was a familiar position, but it wasn't usually me like this – it was usually her! As I settled down onto the bed and adjusted the pillows under me, I realized that it was going to happen, I was in the position and I made my mind up to go through with it.

She found our bottle of lube and sat down on the bed behind me. "Let me put some of this on you and then I'll get ready," she said, "just relax and don't cinch up". I remained motionless and let the weight of my upper body rest against the bed and relaxed the muscles in my butt. It actually felt good in that position – I felt brave and wanton. But, I was startled when she started to apply the lube. First, just a little on the outside of my anus, then little by little, pushing her finger in me – a little more each time, spreading the lube inside as her finger moved in and out. I was able to relax a little more as I enjoyed the feeling of her slippery finger moving effortlessly inside me.

"That's it," she said, "Just relax. I can feel you letting go."

She continued to lube me up, now using two fingers as she slowly prepared my bottom for something we both knew would be wonderful. More and more lube was applied and it wasn't long before my butt relaxed enough to accept her fingers without any resistance at all. Hell, it already felt good, too – I mean really good. I could easily be satisfied with just this.

She climbed off the bed and stood to the side where I could watch her put the black leather harness on and insert the dildo into the holder in front of her pussy. She looked majestic standing there naked with a cock pointing out from her crotch. Her small breasts jiggled as she adjusted the harness and the dildo to where she thought it should be. I looked at the dildo, trying to decide how long it was and how many inches around it was, doing the mental arithmetic to decide if it was going to split me open, or if I could accommodate it in my ass easily. She saw me staring at it and crawled up on the bed just a foot from my face. Sitting back, she began to lube up the dildo, coating it by using the same motions a man would use to masturbate his own cock. I was mesmerized watching her stroke it, knowing it would be inside me soon.

She leaned her head down to kiss me and as I reached my head up for her kiss, I felt one of her fingers touch my well prepared hole. As we kissed, she fingered me and I made an intentional effort to relax my ass as much as I could. When the kiss ended, she asked me if I was ready. I nodded my head to tell her that I was. She reached down to kiss me again, then moved behind me to a spot where she was between my legs and moving closer and closer to my ass.

"I'm going to put a little more lube on you so just be still," she said, "you're doing just fine, relax and enjoy this."

I felt her finger return to it's pattern of applying lube and then sinking into me and withdrawing. She repeated this several more times until she said "Just relax now, you're going to love this."

I felt her place the tip of the dildo against my opening. I started to flinch, but she put one of her hands on my butt cheeks and started to caress me there. "Honey," she said, "Just push back on me a little bit and relax your muscles."

I shifted my weight backwards and felt the tip of the dildo start to press into me. I pressed backwards into her and was surprised how effortlessly the head of the dildo slipped into me and past the ring of muscles. Fuck, it was in me. I felt her start to push very gently and it didn't hurt at all. In fact, the more I pushed back into her, the more it went in and the better it felt. I closed my eyes and began to enjoy the exact feelings she described to me while we were in the shower.

The level of care she showed made me feel loved and special. I felt so vulnerable and helpless, yet proud of myself knowing what was happening. It's hard to admit it, but, the feeling of giving up my ass was genuinely fulfilling. I felt embarrassed and helpless, but, at the same time, I felt good and ready for more. I was a sight, I'm sure, on my hands and knees on our bed with my ass offered up to her, knowing full well that this was a role reversal I wanted so much.

My cock was rock hard as she started to pull out and then slowly move back in. I waited for her to impale me, but it never happened. She worked up to a very slow rhythm with the dildo – the cock – gliding in and out of me. My ass completely gave way now and she started to speed up and push deeper into me. I developed an intense warm and relaxed feeling – the feeling of submission and contentment. As she finally began to fuck me, I relinquished all control to her cock and let myself be completely taken by it.

I reached for my cock, thinking I might as well play with myself while she fucked me, only to find it was leaking copious amounts of pre-cum. I was starting to pant and push back into her wanting to feel the cock deeper in my ass. I started to moan and finally told her "Oh, fuck me now baby, fuck me."

And she did. She began to move with more dedication in and out of my ass and her speed picked up. Judging from the rate of thrusts, I was being fucked at about the same rate as I had always fucked her ass.

"How does that feel?" she asked, "Am I hurting you?"

"No, it's not hurting at all," I replied. "It feels good, it's just like you said it would be. Oh shit, it feels like I'm..... oh, man, I think I'm going to cum......"

I felt the pressure build up in my balls, and it was like a slow motion movie as the sensation grew bigger an bigger until I knew an eruption was imminent. After a few seconds, though, my cock was spewing globs of cum – I could literally feel my sperm escaping my cock in repetitive strong squirts. My body tensed as the orgasm warped through me. Julie told me later that my legs were wailing and my ass was bucking as if to fuck the thing myself.

Finally, I fell exhausted and limp against the pillows and the bed. I remember trying to catch my breath and push the dildo out of my ass so I could stretch my body out. When Julie pulled out of me, there was no resistance and the cock slithered out. When it was out, I felt Julie get up off the bed and go into the bathroom. She returned shortly with a warm washcloth and softly cleaned me up saying, "It's just a tiny bit messy back here, just stay like that and I'll have you cleaned up in just a sec."

I couldn't move. I didn't want to move. I was completely exhausted and spent. Quite possibly, this was the strongest cum I ever had.

As I rested, I felt the warmth of the washcloth gently wipe me down. She didn't say a word as she cleaned me off. I felt her pull my cheeks apart and wipe me down. "Well," she said, "I think we used enough lube, that's for sure. Maybe a little less next time."

Hmm, next time? Yes, for sure. There would be a next time.

End of Chapter 1. Watch for another chapter soon and find out more about Julie's preparations for my fantasy weekend.