The Ride of a Lifetime Ch. 02

I want to thank everyone who rated and took the time to comment on my first story ever. I'm taking some advice from everyone and this is the follow-up. Please read "The Ride of a Lifetime" first. Enjoy

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After I texted Jake back, "I'll be waiting with my panties on".

I didn't know if I was excited or nervous. My head was swimming in a fog and I was shaking. After I collected myself for a minute or two, my mind started racing on things that I have to do to prepare. I wanted everything to be perfect for our first time together. It was still early enough in the day that I had 12 hours to prepare for my hopefully new secret boyfriend. I told my boss I had a family issue and had to take a personal day. He wished me well before turning me loose.

Now my wife was off for the entire day preparing to go to her sisters' house for the entire weekend. Her sisters' house is a four-hour ride west of us. So I couldn't go home just yet as I normally get off of work at 3.

When I left work I drove to this city park that was 2 minutes away. I had to go somewhere to collect my thoughts on what I needed to do to prepare for Jake. I started making a checklist. The first thing that I marked down was to shave my entire body, I'm not really hairy to start with so I figured nobody would really know anyway. The second thing was to find out how to prepare and clean my virgin ass to accept my first cock. A quick google search and I had a dozen ways to prepare. Lastly, I started to think about what I was going to wear.

I was going over what lingerie that my wife had in her dresser and I wanted it to be perfect. I wanted it to fit properly and most importantly I wanted it to be all mine. I wanted it to be new and sexy for Jake, I didn't want someone else's hands me downs that I wore for him.

I knew that I was way too nervous to actually walk into a clothing store and ask for help. Plus I lived in this area and I feared that someone I know would see me. In my head, there were about 100 irrational fears that were spinning out of control. I had a genius idea or at least I thought it was genius, I'm sure someone has thought of it before. After I did an extensive amount of googling men's to women's sizes I had a good idea of what sizes I am. I always have an emergency stash of cash with me just in case something happens I won't be broke. There is a secret pocket in my belt with a small zipper and I keep $300 cash inside for emergencies.

So here's my plan...I looked up clothing stores that had online orders but same day In-store pick up.

I know you're thinking "but you still have to pay with your card." However, you are right but I found a loophole.

The stores that I found had an option to pay with a gift card. So what I was thinking was if I found what I wanted online that I could pick up within the hour I would then go to that store and purchase a gift card for the amount. Then when I get a notification it's ready I'll go tell than that my wife ordered something and I was here to pick it up. So after about an hour of online shopping with some setbacks, I was able to find what I thought was the perfect outfit.

I picked out a black pair of silky and lace panties. The front was all shiny silk and the entire back was a lace pattern that was sheer see through. The garter belt I chose was also black with lace trimmed with a silk border. The stocking I chose went just above my knees. They were the matching pair that had a small red bow on the front. The nighty I chose was black with some red in it to accent the little bows on the stockings. It was almost transparent but it was silk and lace also.

Now on to some heels. I've never worn heels in my life so I know I'm going to struggle to walk in them. I figured I'd buy a pair of shoes that don't have a huge heel on them but looks equally sexy. I know Jake will understand why I did it. However, something in me told me to order a pair of fuck me heels too.

I went to the checkout and found out how much it was, It was $223.57. Perfect just under my budget! Now I know how much to get my gift card for. I pulled out of my parking spot at the city's park to make the 15-minute drive to the store at the mall. As I pulled up to the store I went to the men's section and pulled a gift card. I explained to the gentleman who helped me out that it was for my wife. We thanked each other as I walked away.

Once I was outside I had to contain myself from running to my vehicle. I was so excited I was shaking while taking deep breaths as I entered the gift card code. I looked it over twice to make sure it was correct and hit submit.

My phone gave me a notification tone as I received an email that said: "Thank you for your purchase we will notify you via text when it is ready for pickup in approximately 49 minutes."

I was so excited I could barely contain myself.

I had time to waste so I thought I would head to the convenient store to pick up some things I'm going to need later. I walked in and picked up a ladies razor, a stick of women's deodorant, a disposable enema, some lube with some shaving cream along with a box of condoms. When I walked to the checkout line I checked my phone to make sure I had everything. I used the remaining emergency cash I had to pay. I thanked the young lady as I walked out.

As I got into my car my phone went off, it was a text message. I couldn't get to my phone fast enough hoping my order was ready. I looked at the message, it was from Jake and it was just an emoji of a kiss. I sent him back a blushing and kiss emoji.

My reply was "Can't wait for you to see me later."

My phone went off again so I looked thinking it was Jake again however it was a text from the clothing store notifying me that my order was ready for pick up.

I calmed myself as I headed for the store. I really didn't want to explain to my wife why I received a speeding ticket from the other side of town while I was supposed to be at work. I pulled into the first spot I saw in the mall parking lot, I'm not going to lie I was nervous as hell. What if someone sees me, what if the girl behind the counter knows it's for me, what if I look suspicious... I tucked those fears away and walked in. A nice older lady greeted me and I told her that my wife ordered something online and she sent me to pick it up. I don't know if she believed me or not but she didn't say anything. She went through it with me to make sure it was all here. I said my wife sent me a list of what it was and it appears to be all here. I thanked her and I took the bag from her with a trembling hand.

I still had some time to waste before I could head home to greet my wife and send her off for the weekend. I went around the mall to a less crowded part of the lot and parked. I was so hard and excited as I went through everything. The feel of the material was so smooth and silky I could only imagine what this was going to feel like on my bare skin. I kicked off my work shoes in the car and tried on the heels. I was worried that they would not fit because I kind of guessed on my size. They fit perfect, they fit as if they were made just for me. I remember thinking that they fit better than my men's shoes. I took them off and put all of my purchases away nicely and hid them in the back seat so nobody would suspect anything.

I looked at the clock on my dashboard when I realized that I had not eaten anything today. Knowing that I had to keep my strength up because I have a huge night ahead of me so I pulled into a local fast food joint. I'm sure it's not a good idea to eat a bunch of greasy food so I settled for a salad. I ate inside and took my time. I let my imagination run wild. When I was finished it was time to head home so I took my time as to not get there too early.

When I walked in the door my wife greeted me and asked how work was. We made small talk while I loaded her bags into the trunk of her car. We chatted about what she was going to do this weekend and what I had planned. I told her that I was just gonna do some things around here and relax for the weekend. When it was time to for her to depart I walked her to her car and kissed her,

"Be safe on your drive. If you need something call me. Tell everyone I said Hi. Call me when you leave Sunday, I'll have dinner waiting for you. Love you, honey."

I watched as she drove down the block until the car was out of sight.

I practically sprinted to my car and retrieved my purchases. I walked inside and closed all the blinds in my house and locked all the doors. I set out to get myself prepared for a night I will never forget. I drew myself a bath and settled in with bath bombs that my wife uses. I want to feel and smell as much as a woman I can for Jake. I sat there and enjoyed the smell and feel of the bath bomb. After soaking for a while I decided it was time to shave as much as possible. It didn't take long for me to be smooth. I got myself out of the tub and dried off.

I walked into the bedroom to admire myself in the full-length mirror my wife uses every day. I took out the bag and laid everything out neatly. I put on the high heels to give it my best shot at walking in them. After a few attempts, it was not a pretty sight so I stuck with the lower heels. It was an adjustment but I got the hang of it. Something in me told me to bring them with anyways. I laid on my bed in the nude imagining what tonight will bring.

I was trying to figure out when I should get dressed. Should I do it now or wait. Just then my phone went off.

I looked at it and it was Jake, "I'm leaving my house now, I'll be there for you in 30 minutes. I can't wait to see my girl."

I texted back "I'm waiting for you." with a kiss and smile emoji.

I looked at the time when I realized it was 9:30 pm. I panicked for a minute, telling myself that I won't be ready in time. I calmed myself and slowly slipped my panties up to my waist. The feeling was incredible. I'm trying to control myself while keeping my small hard cock tucked away. I look at the bed and decide to slip into the garter belt with stockings. One leg then the other before trying to fasten the garter belt securely. I feel so sexy and feminine,

I can't wait to complete my outfit. I look down at the bed just to admire my nighty for a minute before slipping it over my shoulders. It feels so natural on me, it's almost like I was tailor-made for my body.

I rushed over to the mirror just to get a glimpse of myself for the first time. I live it, I absolutely love it! I can't contain myself as I feel so giddy. I walk over to my wife's makeup and apply the shade of lipstick she wears all the time. I rush out of the room and back to the living room. I sit on the edge of the couch where I admire my shoes. I sip them on and practice walking in them before my man arrives.

I lose track of the time and then that's when I hear the knock at the door. I run to the door but I hesitate opening it. I know Jake can see me but I start to think.

"What if I'm not what he expected or what if he doesn't like what he sees."

I slowly open the door to see his smiling face as he looks me up and down. He tries to say something to me but he can't get a word out. He takes my hand and gives me a whirl looking me up and down.

He finally speaks "You look absolutely stunning Jackie."

He called me Jackie! I didn't even think about a name but he gave me one that I ABSOLUTELY LOVE!

I invite him inside for a drink before we take our ride. I ask "Do you like what you see?"

He replied, "I've never seen a more beautiful woman In my life."

He pats his lap for me to sit. Before I know what is going on he has his lips on mine holding me closely. My first kiss as a woman. He runs his hands over my entire body while we make small talk. Mostly just flirting and teasing.

He gets a serious look on his face before asking me a question.

He asks, "Why do you want to do this with me?"

I look him deep in the eyes while I lean in for a kiss.

I think for a minute and reply "In my household, I am the breadwinner, I make most of the decisions with input from my wife but I usually make the final decisions. When I'm at work I am a supervisor for my department. Sometimes I feel as though I need to let it all go. I need someone who is dominant and willing to make decisions for us. I just want to sit back and let everything go even if it's only for an hour or two. I want to have a strong man to take charge of me. I'm willing to do as I'm asked if it pleases him."

I'm not really sure why I opened up to him like that but it feels so good to tell someone. He kisses me passionately with the reply "I completely understand and I am going to be that man."

He starts rubbing my inner thighs and my hard cock springs free from being tucked away.

He looks down with a smile "Oh my, someone is happy just look at the wet spot in your panties."

He helps me up while holding my hand as he leads me to the door.

"I believe it's time to go for a ride," he says.

I smile while closing the door behind us.

He opens my door and helps me step into his truck. He even gives my ass a pat before closing the door. I can't believe this is about to happen. I'm sure he has read my fantasy text numerous times because when we pull out of my driveway he asked me directions on where to go.

As we drive through my neighborhood a car passes us and I duck down so nobody will see me.

Jake laughed and said, "First, nobody can see you because my windows are tinted."

"Second nobody is going to recognize you dressed as Jackie."

He made an excellent point and that was enough to ease my mind. He put his arm around my shoulder while pulling me closer to him. He made me feel safe, relaxed, sexy and desired. We teased each other as we drove to our spot with some touching and naughty chat.

As soon as we pulled off of the main streets his tires rolled on to the gravel roads I lean in and start to kiss and suck on his neck.

He said, "I guess we're here?"

I put my hand on his cheek and turn his head while kissing his lips. I break our kiss while going back to sucking his and earlobe.

"I'll take that as a yes?" he replied.

He slipped his hand under my nighty until he found what he was looking for. His hand worked my hard cock over my panties for a few minutes. I had to fight the urge to cum about a dozen times.

When he pulled his hand from under my nighty he pulled me close to him and started to whisper in my ear "Hey sexy would you mind pull..."

He remembered, but I didn't let him finish speaking. My hands went right for his pants and undid his belt and unfastened the button. He lifted his hips enough for me to reach in and find the cock that was meant for me.

I lowered my lips down to his hard cock while he put his hand on the back of my head. I gave the tip of his cock a good firm kiss, I wanted to see my lipstick on him. He moaned as I covered his cock in kisses. I puckered my lips and ran them up and down the sides and top of him. He let out a moan that drives me crazy. I parted my lips and sucked him in my wet, warm, wanting an empty mouth. I could feel him run his fingers through my hair as I slowly bobbed up and down his solid cock. I could tell he was really enjoying the pleasure he was receiving because he was having a hard time keeping his truck in a straight line.

My head was spinning while this was going on. There was no other thought on my kind except pleasing my man to the best of my ability. I figured it's now or never and tried my hand at deep throating. I normally have a bad gag reflex when I'm at the dentist but when I went down it was gone! There was nothing just my empty throat being filled. Now I know I was really made this way. My place in this world was to please this man.

I felt him grab a hand full of my hair and slowly push my head all the way down his cock. It was an incredible feeling when his balls were touching my face. He held me down there for a few seconds before pulling me back up to catch my breath. After each time I would suck him long and hard until he pushed me back down again.

After the 9th or 10th time he did this he pulled me off of his cock and said to me "I don't want to cum yet. There is so much of you I want to explore."

I was a mess, I had drool all over my face and chin, my lipstick was just a little smudged.

He looked at me and smiled while handing me a towel. I dried off my face and saw he had some precum leaking out so I leaned in, puckered my lips and applied it like lipstick.

He told me that he can't take this anymore and we needed to park this truck soon. I told him how to get to this unused service road. I assured him that it was a safe place for both of us. What should normally take about 5 minutes actually took like 2 minutes. I guess he was in a rush. By the way, things were going he must have memorized my fantasy text.

When I told him we have reached our destination he leaned over and held me close to him while we kissed for what seemed like half the night. But In reality, it was about 5 minutes. But it was a really great five minutes. When he stepped out of the car and was making his way to my door I remembered that I had condoms in my high heels shoe box. The way he has treated me and made me feel, I decided that the condoms were not even an option. I want him, I want everything he brings with him as well. While opening my door he put his hand out and I offered him mine as well.

He looked at and said, "You are a very special woman, you deserve to treated as one."

I smiled back and replied, "You are the gentlemen of my dreams and I'm going to care for all your needs."

He accompanied me to the hood of his truck where he bends me over face down. Jake takes both of my wrists in his left hand behind my back while bending over me running his right hand all over my tight ass.

"I've been waiting for a long time to be here with you," he spoke.

I just looked at him over my shoulder while I bit my lip with a sly grin. That's the moment I hear his pants hit the ground. He lifts up my nighty while he rubs his hard cock up and down my virgin ass over my panties. I love that he has taken control of me and the situation.

He released my wrists so he can grab my hips. He slowly slides the tip of his cock in me. I feel a wave of pain wash over me. My body tenses up and he realized it. Jake stops for a minute to let me get used to his manhood in me. After a minute or so I push back into him. He takes my hint and slowly pushes in another inch and stops. He did this for the entire seven inches of him. When I feel his balls on my body I feel light headed.

All the pain has exited my body and was replaced by sheer pleasure. I can't help but think of all the circumstances that have brought us both to this place in time. His hand starts to rub my back while it makes its way to my tight former virgin ass.

He leans in and whispers "Are you ready for me sweetie?"

I look over my shoulder at him while I bit my bottom lip with a sly grin. He slowly withdraws his entire cock from me as he stops before the tip exits. He slowly pushes his cock balls deep in me again. I gasp while I moan again and again. He does this to be about a dozen times.

The last time he does this he stays in me while asking "Are you ready for me Jackie?"

I push back into him "I want you so bad, this girl is going to do whatever it takes to please her man. I want you to take control of me."

He gives my ass a slap before he puts his hands back on my hips.

He takes my words to heart as he takes control of me, my body and the situation. I love him for that. He is controlling the pace and depth of his thrusts. The feeling of my body lurching forward with every thrust has my cock leaking profusely.

I moan his name... "Oh Jake, fuck me, sweetie, use this woman for your pleasure. Your cock was made for me."