The Ride of a Lifetime

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Straight married man now questions everything about himself.
3.1k words
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Part 1 of the 2 part series

Updated 06/09/2023
Created 11/05/2018
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Hi everyone, this is my first attempt at writing. I hope you enjoy and I can't wait to get some feedback from everyone. Please be honest in what you think...I can take it.

This is a true fantasy of mine.

***

I'm a curious man that is married to a wonderful woman but as time has passed our sex life has diminished quite a bit. We still occasionally enjoy really great sex but the days are few and far between.

I do enjoy porn when I have to take care of my own needs in between those days. I like to set the mood when my wife is at work. I strip naked on the bed with my tablet. No lights on in the room just the soft glow of the tablet screen. I have my towel next to me and I let my imagination run wild. I'll slowly stroke myself to a few videos before I find the perfect video to cum to. I found a great clip that had a very sexy lady in lingerie and she was on her hands and knees with a muscular man behind her with an average size cock pounding away at her ass or so I thought. After a minute or two of watching this the man flipped her over and I was a little shocked to see that the woman had a pretty decent cock that was at full attention and she was jerking herself off. I'll admit that I was a little taken aback but not enough to turn it off. Actually the opposite happened and I noticed my own cock was incredibly hard and before I knew it I was jerking myself to a hard and intense orgasm. I laid there for a minute and thought to myself what just happened, what did I just see and why did I get so turned on by this. I cleaned myself up and put everything back in place so my wife wouldn't know what I did before she got home from work.

However that entire week I could not stop thinking about what I saw and everytime I would get so turned on and hard. Then one day while I was driving home all I could think about was what it was like to be that girl. I was so horny that when I walked in the door I didn't jerk off but I waited for my wife to get home. When she walked through the door I grabbed her and kissed her passionately. She did not expect this but she went with it. When we entered the bedroom I took her clothes off and left her standing in her bra and panties. I was so focused on her silk and lace bra and panties that I didn't even take them off of her. I bent her over the bed and pulled the back of her panties to the side and slipped deep into her. It didn't take either of us long to cum. I came as deep as I can in her and she came all over my hard cock. I kissed her on the lips and thanked her. We went on about our day. But for some reason I couldn't get the image of my wife's silk panties out of my head.

That night as I drifted off to sleep I had a dream where I was in my room but I was in a pair of panties, bra, garter belt, stockings and a nighty. I was in the same position that I had my wife in and there was someone behind me but I couldn't make out his face. That's when I was jolted out of a sound sleep, my heart was racing, I was out of breath like a just ran a mile and I had sweat on my brow. That's when I realized in my dream when I looked back I couldn't make out HIS face. I put my hands on my face trying to figure out what was happening to me.

The next day at work I had a hard time focusing on the task at hand. I was so flustered that I left work early. On the drive home something deep in me took over and I rushed home. I thought if I tried on some of my wife's underwear maybe it will satisfy whatever was in me and I could put this behind me once and for all. I was shaking as I open her dresser drawer and pulled out some of her lingerie. I slipped it on and had the sudden urge to watch some porn. I logged on to my favorite site. I brought up the first video that I found when I searched "Crossdresser" I noticed that there was a link in the corner that said "chat with likeminded people today". I figured what can it hurt to chat maybe someone out there has gone through what I'm experiencing now. I clicked on the site, made a username with a short bio and waited for someone to get back to me.

After a few messages from other guys one message caught my eye. His name was Jake and I introduced myself too, "Hi I'm Jack". He was a married man that was a few years older than me, I was 36 he was 40. We chatted for a little while before I confided in him my secret. He was understanding and seemed to know what I was going through. I told him that I'm straight or I think I was and he said he has never been with a man but he had a fetish for men in panties and lingerie. For the next month or so we chatted via email and text everyday. We chatted about everything from the weather, to what was going on with us in our life and how it was another day that we didn't have sex with the wives. It was just a matter of time before the talk turned to me dressing up in clothes. For some reason I connected with him on a different level. He was always nice and respectful. I think that's why I took a liking to him and he knew what to say to me. He really made me feel comfortable in my own skin. He assured me that I was not alone and there are so many other guys that feel the same way as I do. He also made it clear that there are some men out there that appreciate a sexy crossdresser like me.

We had a conversation one night about wearing panties under my work pants for a day to see how it feels. I agreed with him that it would be a turn on to know that only myself and Jake know my secret. One day at work I was pretending to look busy in front of my boss when my phone buzzed in my pocket. I looked and was surprised to see Jakes name on my screen. I read the message and it simply said "Your Fantasy?".

Well that made me think about the fantasy that I always wanted to do with my wife but she didn't feel comfortable with it so I never pressed the issue and just left it as a fantasy.

However, more and more that I thought of it and imagined it in my head I didn't see my wife in it anymore. I was playing the role that she was in and Jake was in my position. I was so turned on that I took an early break and rushed to the bathroom. I took the corner stall and pulled my pants down and rubbed my cock over my panties until I couldn't take it anymore and jerked myself off. I've never came so fast in my life. I cleaned myself up and slowly slid my panties back up around my waist. Feeling that silky fabric slide over my cock I was hard again. I texted Jake back and told him that I was thinking about his question and had to rush to the bathroom and stroke my cock thinking about it. I explained to him that my original fantasy involved me and my wife but now I see myself playing her roll. He texted me back and said he was more than excited for me to tell him...So here we go.

"After dark when my wife leaves for the night to go to her sisters house you show up in my drive way. You knock on my door and I open it wearing panties, bra, garter belt, stockings, lipstick, heels and a lacy nighty. You tell me how good your girl looks then you pull me tight to you then kiss me passionately. You take my hand and lead me to your truck and open the door and help me in the passenger seat. You climb in the cab and we start to drive. I slide closer to you and run my fingers through your hair. I kiss, lick and suck on your neck and ear lobe. We finally get to the secluded back roads that I told you about when you slide your hand under my nighty and rub my cock over my panties. The feeling of your hand rubbing my cock over my silk panties gets me so hard and turned on. You put your arm around my neck and pull me close to you as you kiss my lips and whisper in my ear "take out your mans cock, I want to see your lipstick on it". I look you in the eyes and give you a big smile as I lean over and undue your pants. I pull your boxers down and free your big hard perfect cock. It's 7" shaved and looks delicious, almost like it was made just for me.

I lean over and give the tip a kiss good enough for my lipstick to leave lip prints on it. I lick your cock up and down like it's a tootsie pop. I hear you moan and feel you put your hand on the back of my head. I pucker my lips and run them up and down the side of your cock. I wrap my lips around the tip of your cock and drool all over you before taking my first every cock down my throat as far as I can. I give you a long slow wet blowjob. I can tell you are enjoying it as I notice that you are having trouble driving in a straight line. My lips going up and down your hard shaft over and over again. Every once in a while I can feel your hand on my head push me all the way down on your cock and hold me there for a few seconds before letting me up so I can catch my breath. I can't help but think how easy and natural it feels to have a hard cock in my mouth and deep throat. Never in a million years would I have ever though this would be happening. I want so much more of you. I can tell by your moaning and breathing that I am satisfying my man. I pick up the pace and hold my lips tighter as I give you long strokes with my lips.

You pull my mouth off of you and give me a deep kiss. I lean back down and rub your pre cum all over my lips giving it a shiny look you can see in the head lights. You tell me that you want more and I tell you that I have a spot about 5 minutes away. You joke that you might not be able to wait that long. I have you pull off to this unused service road that I know of and park in the back where nobody will see us or think to look for anybody back there. When we reach our destination you pull me tight to you and kiss me like you would kiss your lover. You make me feel so sexy, so feminine and so desired and I love that. You open your door then slide out and walk to the passenger side of your truck and open my door.

You take my hand and help me out of the cab where you walk me to the hood of your truck. You proceed to bend me over the hood while you tug my panties down around my knees. You grab both of my wrists and pull them toward you. I hear your pants hit the ground and feel your hard cock run up and down my virgin ass. I bite my lip and moan your name. I want you so bad right now. You let my wrists go and I feel you lube up my tight ass. I feel your strong hands grip my hips while you pull me on to your hard cock with firm steady pressure. I feel slight pain as the tip slips past and enters me. My head is spinning with lust. I can help but think what has happened to me, what have I become, deep down inside did I always want this, do I want more of this and the big question is why do I love this? Your hands firmly hold my hips steady as you slowly slide all 7 hard inches into me.

When your balls come to rest on me you hold your cock still deep in me so I can get used to the feeling. While I adjust to you in my body the burning and pressure has subsided and know all I feel is a sense of fulfillment, a sense of fullness and sheer pleasure that I have never in my life experienced before. It's something that I want to experience often. I'm begging you to fuck me. I want you to treat me like a real woman. I feel you pull almost all the way out of me and slowly thrust all the way back into me. The feeling is amazing as you do it again and again. I'm moaning your name "Oh Jake, Oh Jake mmmmmmm...faster, harder, give it to me." I reach down to jerk my own cock but you stop me. You tell me that I'm not allowed to cum yet, you will make me cum when you are ready. I'm in no position to argue with you so I do as I'm told. The tip of your cock is rubbing something deep in my former virgin ass and I feel as though I'm going to cum from that but I resist the urge. I want you to fuck me good and proper. I'm begging you to cum deep in me, I feel you pick up the pace and tell me that I'm the best piece of ass you ever had.

I feel so vulnerable right now in the woods, dressed up in women's lingerie, bent over the hood of your truck in front of your headlights with a real mans cock buried deep in me pounding away. I can still feel your hands gripping my hips tight slamming your cock into me. I lurch forward with every thrust moaning and breathing hard concentrating on every thrust. I hear you start to moan louder and faster and I'm hoping that I'm going to get my reward soon. I beg you to give me your warm thick cum. I want you to coat my insides. "Cum in me in, I want your cum in me, I want you to own me. As soon as you cum in me I will be all yours and only yours, you will own me" I want to keep your first of many cream pies in me for as long as possible. You dig your fingers into my hips and pull me as tight to you as possible and you grunt "I'm cumming baby...I'm cumming!" I close my eyes and concentrate on your cock that has swelled up and is twitching in me. I can feel a warm sensation in me. I've never wanted this more in my life. Your cock slowly slides out of me and I can feel your cum slowly leaking out of me. I stand up and turn around to face you that's when you kiss me and bend down and pull my panties back up to my waist.

I see your cock covered in cum so I get on my knees and take you into my mouth to clean you off. I wouldn't want to waste one drop of your precious cum. Once you are all cleaned up you help me to my feet. You have me bend over so you can see your cum leaking out of me and making a mess of my panties. You help me back into your truck and that's when you tell me it's my turn to cum for you. You slip your hand into my panties and grab my hard cock and slowly stroke me. You look me in my eyes before telling me I have your permission to cum. It doesn't take long to jerk me off after what I've been through. I explode in your hand. I have never cum this hard with anyone before. You hold your fingers to my lips and have me lick my own cum off of them. When they are clean you pull me close to you while you have your arm around me stroking my shoulders."

I'm shaking and incredibly horny at the same time as I read over the entire text to make sure that I didn't leave something out. I'm pretty satisfied with what I see. I stare at the "Send" button for what feels like an eternity but was actually just a minute or so. Well I think to myself it's now or never I guess as I send it. My heart pounds and I'm physically dizzy as I stare at my messages waiting for a reply. My phone vibrates and I'm trying to open it as fast as I can but I keep putting in the wrong pass word. I collect myself for a second before slowly typing in my passcode.

It simply says "When does your wife leave?"

I reply "5pm this afternoon and won't be back until Sunday night" pressing the send button again. Just as fast as it send Jake replies "Be dressed and ready tonight 10pm sharp I'm picking up my girl"

I'm so excited that I reply back "I'll be waiting with my panties on"...

***

I hope you enjoyed this as much as I enjoying telling everyone about my fantasy.

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AnonymousAnonymous7 months ago

So hot to be anally penetrated while wearing a tight pretty bra…

cdCindy1cdCindy1over 5 years ago
loved this story

I too am a married sissy CD sub who loves sucking cock and getting fucked. I haven't done it in public like in your story but I would love to -- this really turned me on reading about being fucked in public. I can't wait to read the next chapters. thanks for this story.

MarieJoanneMarieJoanneover 5 years ago
Beautiful

Well done and I relate totally. I am also in a sexless marriage and over the last year or two my fantasies all now turn to me being crossdressed and being taken by a man. I now regularly dress up when home alone and usually manage an evening or two a week as Marie. Your fantasy is much like (one of) my own. Well done. I feel excited t be part of such a sisterhood.

missyoujaynemissyoujayneover 5 years ago
I enjoyed your story, and I've written something similar.

I've written a story, but not submitted it yet... A guy keeps his cross-dressing a secret from his wife. He has fantasies about what would happen if he went out dressed as a slut, which get sicker and more outrageous, yet more intoxication and alluring, as time goes by. He fears that if he had the chance, he may not be able to control himself, and really would go out dressed as a slutty hooker.. So he swears to himself he must never, ever go out of the house dressed like that.. But because he knows he'll never get the chance anyway, he lets his fantasies get more and more debauched and self-destructive, to the point where he only gets aroused when he is day-dreaming of being captured when he is dressed like a sissified slut and unstoppably forced to submit to all kinds of disturbing humiliations..... the more degrading and disgusting, the better...... Then.... the day comes when his wife does have to go away for a couple of weeks..... Oh, dear...

Danielle_CD58Danielle_CD58over 5 years ago
Good story

I liked it and I think you should continue. I want to know what happens <wink>.

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