Rest Stop Romance Ch. 04

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After being ditched, Rose is picked up by her neighbor, Tom.
3.7k words
4.52
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Part 4 of the 4 part series

Updated 09/22/2022
Created 03/05/2013
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~The following is entirely fictional and just a fantasy of mine. Any likeness to actual persons or events is unintentional and coincidental. Since Ch. 02 is still my highest rated story and was my first to get that little red H, here's Ch. 04! The saga continues again!~

*****

-Rose's Perspective-

It had been almost an hour since I had called my next door neighbor, Tom, to come pick me up from this damn rest stop. It was almost funny, to think that just a few hours ago, it held so many fond memories. Memories of losing my virginity as I gave myself over to a man for the first time. A passing trucker had seduced me by whispering sweet nothings before I sucked his cock and let him fuck me in the ass on the picnic table I now sat on, waiting for my next door neighbor to come pick me up. That's when I finally realized something important. Tom didn't know my secret.

No one knew that Tommy, the shy, quiet college student in the neighborhood who lost his mother to cancer two years ago spent his free time dressed up as Rosalie, or Rose for short, a 20 year old girl who, as of six days ago, found out she really loves big, hard cock. A sense of panic began to sink in. I didn't bring any "boy" clothes. I was supposed to spend the whole week with the trucker I thought was my boyfriend, as Rose on a cross country trip. I had no way to explain to Tom, why I was here at this rest stop, wearing a button up dress, pumps, and a wig with my bag full of wigs, dresses, lingerie, and other female clothing. I was twisting my hair in my fingers, as I realized I tend to do when I'm nervous, when I realized Travis and Dave's cum had gotten on my black wig. I grabbed my bag and quickly ran to hide in the Ladies' room.

I rook the white bow out of my wig, took the wig off and threw it away. I reached into my bag and grabbed the first wig on top. It was, by chance, my favorite long, brunette one. I fixed it to my head and checked myself out in the mirror. I looked like a trainwreck. My make-up had smeared from crying while I was sitting on the picnic table, so I washed my face and re-applied my make-up. It was time to be strong. I had a lot of explaining to do when Tom got here. I might as well look my best. I looked in my bag, and grabbed what I was supposed to wear on my last day with Dave.

*****

-Tom's Perspective-

I pulled into the rest stop Tommy told me he was stranded at and looked around. He sounded hurt on the phone, and his voice almost sounded a few octaves higher than usual. I was almost certain he nearly called himself another name too. I shook it off, only worrying about finding him and getting him home safely. I circled around to the picnic area and parked. The picnic tables offered a full view of the main entrance where the restrooms were. Tommy was nowhere to be found. I picked up my phone and dialed his number.

"Tommy? It's Tom. I'm at the rest stop you said you were stuck at. I don't see you. Are you still here? Are you okay?"

"I'm... better now. I'm in the restroom. Wait over by the picnic tables and I'll be right out." His voice sounded higher again. "And, Tom?" He asked in an almost feminine tone, "pretty please don't freak out."

"Freak out? About -" was as far as I got before he cut off the conversation by hanging up the phone. I sat down on the picnic table closest to the rest stop and I was nearly breathless when I saw HER. The brunette I saw leaving Tommy's house six days ago walked out of the women's bathroom. She looked even more stunning than the first time I saw her. Her skin was glowing in the sun, her long brown hair fell gently on her shoulders. She was wearing a beautiful pink sleeveless dress. There was a black belt under her breasts pushing them up a little. The neckline wasn't low, but high enough to leave some things to the imagination. She also wore a pair of black, strappy pumps with a 2 inch heel and bows on the back the color of her dress. She was also carrying a large duffel bag. She walked past me and set her bag on the table, giving me a look at the heart-shaped open back of her dress. There were no visible bra lines. She was even more gorgeous up close than when I saw her leave Tommy's house with the trucker six days ago. With her 2 inch heels on, she was standing at about 5'8. 3 inches shorter than me at 5'11. She couldn't weigh anymore than 125-130 lbs soaking wet.

"I- I mean, I'm sorry ma'am but I'm looking for someone. Kind of small guy, about you're height. Have you seen him?" She let out a small, but clearly happy giggle. It was adorable.

"Tom, it's me. Tommy. But I go by Rosalie, or just Rose for short, when I'm dressed like this." Suddenly, everything clicked. The truck parked over on the other side of the rest stop was the one in front of his house last week. The brunette that left wasn't Tommy's friend... She was him. He was her... I was confused, but not angry. I was still so attracted to the girl in front of me, even though I just found out she was a boy. And my neighbor. I looked her over again, from head to toe. My eyes tracing every detail from her heels, up her glowing legs, to the skirt of her dress, up her smooth, flat waist to her C-Cup breasts (forms I was guessing now), to her perfect make-up, and of course, that flowing brown hair. I must've been taking too long to reply, because her eyes started to water as she looked away...

"I'm sorry, I've never told anyone this... I don't know how to, I -"

"You're beautiful." She stopped stammering and looked at me. She smiled a little but then looked away again.

"The last man who told me that, fucked me for six days in a row on a "cross-country" trip in his truck." She said, lowering her head, "I thought he liked me. He just brought me back here and left me like a used up toy."

I could tell that he, no, she, had been through a lot in the past six days.

"You don't have to, but you can tell me about it on the ride home if you want. Get your bag. Let's get you home, sweetie." I thought about calling Tiffany and telling her Tommy was safe, but I thought I'd rather let Rose tell me her story first.

-Rose's Perspective-

Tom grabbed my duffel bag for me and put it in the back of his car. He ran around the front of his car to the passenger side and opened the door for me. I didn't realize it at first, but he was treating me like a lady. He was a true gentleman. I got in the passenger seat and buckled up as we left the rest stop behind. I started from the beginning. I told him about how I started dressing in secret after Dad left, and how it became an every day thing after Mom died. I told him how I kept Mom's room locked. It was my inner sanctum. My refuge. I never even let Tiffany in there. No one until Dave. I told him how we met at the rest stop, I told him how he fucked me on the table we were sitting on. I told him about going home that night and how he fucked me for what seemed like hours on my Mom's old bed. He asked me about Tiffany, and how I planned to tell her all this. I said I didn't know. He then asked me another pertinent question I hadn't considered until he asked me.

"So, do you only like men? Sexually, I mean? Tiffany always says you never make a move, so..."

"I... I don't really know. I never thought about it until now. All I know, is I really liked him fucking me, and sucking his dick. It just felt like everything was right in the world while I was with him. He made me feel like a woman, and I think that's what has been missing from my life."

"So, do you want to be a girl all the time? Instead of just dressing up I mean."

"I think so. No. I know so. I want to be a girl. I feel like it was what was meant to be. I never fit in with other boys. I've always been so small... I never made a move with Tiffany because it didn't feel right. Now, I think I know why. I think to answer your first question, yeah I only like men. Or at least, I only like cock." I stopped for a second as he laughed a little. I blushed, "Sorry if that was a little unladylike of me."

"It's okay, Rose. Let's get you home and get you inside." He pulled into the driveway and again, he hopped out and ran around to open my door for me. He insisted on carrying my bag inside. I let him. I took a look around and breathed in. It felt good not only to be home, but to be out in the open. In the daylight outside of my house. I walked up the walkway to my front door, listening to my heels clack against the cement. Tom was standing outside the door, waiting for me. He had already set my duffel bag inside the landing. I looked up at him and smiled.

"Thank you, Tom. For not only picking me up, but I feel so much better now. After talking to you." It was the truth. I don't think I've ever been calmer than I was in this moment.

"You're welcome." He said with a warm smile. "I guess this is your stop, young lady?" I giggled. He wasn't but 4 or 5 years older than me. He turned and headed towards his car, but I didn't want to be alone right now.

"Tom?" I called after him, "Would you like to come in for coffee?"

"I'd love that." He answered with a smile. Something about Tom gave me a different feeling than with Dave. My stomach was fluttery. I was almost nervous, but happy. He followed me inside and I motioned for him to sit on the couch. I went in the kitchen and made us both a cup of coffee. I brought them over to the coffee table, my heels clacking on the floor as Tom seemed to be watching my every move. I realized he was looking at my legs. I sat down on the couch next to him, and crossed them as femininely as I could.

"Thank you again, for today, Tom. I don't know if I can ever repay you. I know I said I think I only like men, but I might have to swear off of them for a while after dealing with that pig." He smiled softly.

"You don't have to repay me. Well, maybe there is one thing you can do for me?"

"What's that?" I said coyly, but I could already feel where this was going. And I was all fluttery again. I knew what he was going to say next and I wanted it. Badly.

"Let me show you, that we're not all like that shithead trucker?"

"If you say so." I said as I looked up into his eyes. He leaned towards me, and I brought my lips up to meet his. Before long, we were locked in a passionate embrace. I had my arms up around his neck, and he had his hands on my waist. He leaned farther forward until I was laying on the couch on my back while he was on top of me. His tongue began exploring my waiting mouth as mine went to meet his. We made out on the couch for what felt like 30 minutes before I couldn't take it anymore. I was way hornier than I had ever been. I need him. Now. I broke off the kiss, and whispered in his ear.

"Let's go upstairs." He needed no further encouragement. He lifted me up, I wrapped myself around him as he carried me up to my mom's old room.

-Tiffany's Perspective-

I spent the last two hours trying to call Tom's phone. I hadn't heard anything from him since we talked when I was getting ready to get on the plane 5-ish hours ago. My boyfriend has been missing for almost six days with no word from anyone and this guy can't even answer my call? It didn't matter anymore any way. I was pulling into his driveway. His car's here. So is Tom's. I felt so relieved as I turned my car off and headed to the door. Tom probably found him and they were inside doing whatever it is guys do when they're all alone. That's probably why Tom never answered. I walked up and unlocked the door with the spare key Tommy gave me when we started getting serious. I walked inside and noticed a strange duffel bag on the floor. I didn't let my curiosity get the better of me and left it alone. I walked over to the living room and saw two full coffee cups sitting on the coffee table. They must've left them there. I was about to turn around and call Tommy's name, but I heard a strange sound. I heard what sounded like a woman moaning.

At first, I thought maybe they're watching porn. But then I remembered, I've NEVER heard or seen Tommy watching anything like that before. Besides, these moans were too loud to be on a TV or computer. They sounded too real. That bastard. I go on a trip with my parents, and he brings some bimbo over for a threesome with his neighbor that he "never talks to"? I decided to walk upstairs and get a better look so I could catch him in the act. But, his bedroom door was wide open. I looked inside and there was no one there. I heard the little slut giggle and then moan again before the moan was muffled. Either by a cock or a kiss, one of the two. I knew the sound. I spun around and looked down the hallway when I realized where it was coming from. His mom's room? He never goes in there. He never lets anyone in there. What the hell was going on, today? The door was cracked slightly, like someone tried to close it in a hurry, or while embracing some whore who was probably in there with my boyfriend. I walked up and pushed the door open slightly.

What I saw was so confusing. I clothes strewn all over the floor. A mix of a man's and a pink dress, face down showing a heart-shaped open back. Boxers, a pair of pink lacy panties, men's sneakers, and a pair of black pumps with pink bow on them were all in random spots on the floor. I followed the trail of discarded clothes to the bed. There were only two people in the bed. I saw Tom immediately. He was grunting and thrusting in an out of what I assumed was the woman I heard moaning from downstairs. He was kissing her as he pumped his cock in and out of her. If I didn't think that whore he was plowing into was taking my boyfriend from me, I'd actually think it was kinda hot. He kept plowing in and out of her until I saw her legs wrap around him. He stopped and I heard her feminine little voice ask to ride on top now. They rolled and I finally got a look at the man-stealer.

She was actually really pretty, and not in a slutty way. She looked cute and innocent. Her brown hair splayed over her shoulders. She was wearing a slip with a low back and a strapless bra. She must've had it on under that open back dress tossed listlessly on the floor. Her small fingers and toenails were covered in purple polish. Her face wasn't too heavily made up. She had a natural look to her make-up. Her face actually seemed kind of familiar. It was getting harder to hate this girl because she didn't look like a whore, and Tommy was still nowhere to be seen. I watched for a few minutes as Tom grabbed her by the hips and began bouncing her up and down on his cock. Her slip bunched up and things became a whole lot clearer.

She had a cock too. It popped out from under the bunched up slip. It took mere moments before I began piecing things together. Tommy wasn't in this room. Just Tom, and this girl. On a closer look, her perky C-Cups were breast forms. She had a cock. She was a boy. Her face looked familiar. This girl wasn't stealing my boyfriend. She is my boyfriend.

I looked over at the open closet door and found more evidence. There was no dust or anything on the clothes in the closet, or in the dresser. There were nightgowns and other lingerie handing from the door, that looked recently worn. All of the clothes looked recently worn, like a girl was still living in this room. Apparently, there was. My boyfriend wants to be a girl. Or at least, he's dressed like one in a wig, and full make-up while bouncing on the neighbor's cock.

I didn't know what else to do, so I closed the door softly, and walked back downstairs. I saw the duffel bag again and this time, I opened it. I saw lingerie, dresses, make-up, and wigs. I pulled out a black wig that looked similar to my own hairstyle and noticed there was something sticky on it. Out of morbid curiosity finally getting the better of me, I smelled it. Cum. There was about six days worth of women's clothes in that bag. I know where he went now. I just didn't know why he was back and getting fucked by the guy supposed to be looking for him... Or her. Or whatever. I went out to my car, got in and just drove off.

-Rose's Perspective-

I thought I heard what sounded like the door to my mom's room shut, but I didn't care. Tom and I were in the middle of the most intense and passionate love-making of my life. He spent what felt like two hours fucking me on my back. I would match his rhythm which each moan and giggle as he kept going in and out of me. His cock felt so much better than Dave's. It wasn't as thick, but it had to be an inch or so longer. His cock touched places inside me with each stroke in that I didn't even know could be touched. He went for a condom but I said no. I didn't want anything between me and him. I wanted to feel him inside me and only him.

"Mmm. Let me ride your cock, baby." It didn't take much convincing. I locked my legs around him and we rolled over. I sat up and then plopped back down on his groin. Now straddling him, with his cock still firmly in my ass, I felt him grab my hips and lift me up almost all the way off. I didn't want to come off yet, and he knew. He slammed me back down, shooting pure pleasure up my body as I went down and his cock went further up into me. He began taking control and I let him. The slip I had been wearing under my dress, and still had on, bunched up and exposed my little she-cock but I didn't care. Tom had me by the hips and kept bouncing me up and down on his cock. I giggled and moaned with each jolt of his cock pushing into me. That's when I heard what sounded like the door close.

I sat myself all the way down on his cock, and planted myself on his groin.

"Mmm. Rose, I'm about to cum." I began grinding on his groin, his cock all the way inside me now. I clenched around it and I started grinding in a circle. I leaned down and kissed him as he rolled us over again. He pulled his cock almost all the way out and then with gusto, slammed it all the way back in. I screamed in pleasure as he bucked into me with my legs in the air. He pushed his groin fully against me and I heard him grunt as his cock began to spasm. I then felt jet after jet of warm, sticky liquid began shooting into my ass. He must've hit something with one of the jets because my body began to tremble all over as I felt my own cum shoot out onto my stomach with such force I had never felt before. There was so much cum on my stomach and I could fill so much filling my ass. I felt his cock begin to soften inside me as we separated from each other. Neither of us said a word. We didn't need to. It was the most amazing sex either of us had ever had.

Tom fell next to me on the bed, still panting and sweaty. I snuggled up next to him. I wrapped my legs around his leg and but my head on his chest. He wrapped his arm around me tightly, and we both drifted off to sleep.

*To be Continued*

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AnonymousAnonymous12 months ago

Why was the story stopped, try to continue this story line, this is my fantasy

Getting fucked by next door friend, be his sissy girl friend and be a submissive slut to him, getting my ass pounded by him, deepthroating his cock, giving him sloppy blowjobs, getting my face covered with him cum, bent over and getting fucked on all four with his cum covered and dripping from my face,

jillgurl69jillgurl69over 6 years ago
Very HOT !!

I can relate to how Rose must feel, please continue this wonderful story, I'm so wet right now, I may have to find a trucker or neighbor myself.....

LunaTardLunaTardalmost 7 years ago
Awesome!

I just happened upon this story and really got into it. I really do hope you continue writing it because it's a fun read =D

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