Karlie's College Adventures

I was actually smiling at my phone as I read the last part. I quickly opened the folder I kept my Karlie photos in. I scanned through them repeatedly trying to pick just the right one. I felt giddy as I did.

I finally selected two photos. I was in full dress in both. In the first, I was a sexy little black dress I had liberated from my mom's donation pile. I had been wearing tan thigh highs and a sexy pair of ankle strap heels. The second photo I had temporarily died my hair a dark brunette. I was wearing a sun dress, also from mom, and some wedge sandals.

I attached them both and began a reply.

"Richard. That all sounds really great. I want to meet someone safe that I can learn from. I'm really shy about all of this. I love dressing, but I really feel like I want to go a little further. I've attached a couple pics of me. I hope you like. Karlie"

I was greeted with another quick reply.

"Karlie... Oh my god, you look amazing honey... I really mean that. You're really a sexy young lady. It sounds like we are a perfect match. I love you as a blonde. If you'd like, let's get to know one another and get comfortable with each other. There won't be any pressure from me."

When he said that, I felt better. We exchanged emails for a couple weeks. True to his word, there was never any pressure. He was always warm and sweet and he made me feel completely comfortable. We finally exchanged phone numbers and would talk at least once a day.

He was 53 and had been a widow for about 2 years when he lost his wife to breast cancer. He said he had been curious about cross-dressers for a long time, but had never acted on it. He said he had begun to think about it again recently. He had posted several ads but I was the first response he had thought about pursuing.

Finally, after about 4 weeks, I felt comfortable. I knew I was ready to do it. I told him on a Thursday night. He was really excited, but he did ask if I was really sure. I told him that I was. We made a date for 8 at his house on Friday night.

I was too excited to really sleep that night. I probably tried on everything in my closet 3 times. I finally selected a long sleeved black dress. It was very clingy and hugged my body all over. I would wear a sexy black bra and thong I had just recently purchased on-line. I paired them with a lacy, black garter belt and black Cuban heel stockings I had.

The alarm the next morning was a terrible shock but I quickly dragged myself from my warm bed and trudged off to class. After I was finished for the day, I rushed home and took a quick nap. When I woke, I ran a nice warm bath and soaked for a long time. I had shaved the day before, but I ran over everything one last time. I felt like I was super smooth. After I dried, I put on some moisturizer. I looked at the clock and it was already almost six.

I felt really nervous so I poured myself a little glass of wine. It helped me relax as I put my makeup on. I spent a long time making sure everything was perfect. I had selected a deep red for my lips.

I looked at the clock again and it was after seven! I knew I had to hurry. I quickly put my bra and panties on. I had some B cup breast forms that I used. I had wanted to get bigger ones but I didn't think they would fit my slender frame. Finally, I slipped the silky black stockings up my smooth legs and attached them to my garter belt. I had already straightened my blonde hair. I stood in front of the mirror.

"Tonight's the night," I said to myself.

I put my dress on and decided to have another small glass of wine. After I finished, I grabbed a bag I had packed with a change of clothes and snuck out of my apartment to the back stair case where my car was parked.

I quickly drove the 20 minutes to the upscale neighborhood Richard lived in. I found his address and pulled in the driveway. I saw that I was about 10 minutes late for our rendezvous. He had an impressive home. I couldn't wait to see the inside. After looking briefly around, I got out of my car and walked to the door. I felt like I was about to faint I was so excited. The click of my heels on the side walk seemed almost deafening.

I rang the doorbell. The wait for the door to open seemed so long. Finally I heard the lock being turned. Richard opened the door with a big smile.

"Wow! You look amazing, Karlie."

I blushed and simply said "Thanks."

"Please come in." Once I was inside the door, he gave me a quick kiss on the cheek. I was a little shocked at first, but it had been nice. It made me feel better. He was taller than I thought. He was easily 6'2". His photos hadn't really done him justice. He was in great shape, even for a guy 20 years younger.

He took my hand and led me into his spacious great room. There was a large overstuffed couch with a low table sitting in front of it. There were two glasses of wine and some chocolate on the table. I glanced at him and he winked at me.

"I'm trying to be a good host," he said.

"Yes. I see that," I smiled.

He led me to the couch and we sat down. All of a sudden, I felt very nervous again. He offered me a glass of wine and I quickly took a sip to try and calm myself down. We sipped our wine and talked about how our days had been. He was a senior manager for an engineering firm. He knew I was a student and he asked how my classes had been.

I looked around the room and saw pictures of his late wife. I also saw a picture of a girl about my age. I assumed it was his daughter. From a distance, she looked a bit like me!

We chatted a bit more and sipped our way through a second glass of wine. It was definitely having an effect on me. I finally felt like I was relaxed. He leaned over to me and whispered in my ear.

"Karlie. I want you to be comfortable sweetie. I don't want you to feel any pressure."

"I don't. You've been perfect with me," I replied.

"I'm glad to hear that." He began lightly stroking my nylon clad knee. "May I kiss you?"

"Yes," I said, almost breathlessly.

I had only kissed a girl a few times so I was a little unprepared when our lips met. However, I followed his lead and was quickly into the flow of things. Our tongues met and danced. I love the feeling of having this big strong man kissing me. While we continued to kiss, his hand was caressing my arm. He slowly moved it back down until it was on my thigh. He lightly stroked the silky nylon of my stocking.

I found myself quickly becoming aroused. It was making me a bit uncomfortable since my little clitty was so tightly confined in my little thong. I felt Richard's hand slowly begin to make its way up my thigh. It reached the hem of my skirt and continued onwards. His fingers found the welt of my stocking and quickly traced out the clasp of one of the garter straps.

He stopped kissing me momentarily. "I love that you're wearing stockings, Karlie. You don't how sexy I think that is." I managed to smile briefly before his lips once again met mine.

His fingertips continued to move higher along my thigh. I felt an almost electric feeling as his fingers traced along the smooth bare skin above the stockings. They made momentary contact with my swollen little clitty through my panties. I actually shuddered when he touched me. Sensing my enjoyment, he teased me a little more before moving his hand away. I was a little disappointed, but I reminded myself, I was here to make him feel good.

I moved one of my hands to his lap. I found that he was very hard as well. I lightly rubbed him through his slacks. This brought out a deep moan from him as we continued to kiss. I was getting even more excited now that I was touching him and hearing him respond. I continued to rub him for a little while longer. Finally, I couldn't wait any more. I had to see it and have it in my hands.

My hand reached for his zipper and I swiftly pulled it down. My other hand began un-fastening his belt and pants. I reached a hand inside and soon found his rock hard cock. I pulled it through the fly of his boxers and began stroking it. He moaned again.

I looked down at it. He was probably close to 7", but thankfully he wasn't overly thick. I looked back at him and he nodded. I smiled at him briefly before I slid off the couch and knelt on the carpet on my stocking covered knees.

I lowered my face into his lap and examined his cock closely. It looked so good. I stuck my tongue out and licked a drop of pre-cum that I had squeezed out with my stroking. I enjoyed the taste and started licking all around the head. My head spun as I savored the feeling of finally having my mouth on a real, hard cock.

Richard moaned and began to gently rub my back with one of his strong hands. I opened my mouth and slowly took the head in. God, he felt so big. I was thankful I had spent so much time with that dildo in my mouth the last few months. This was so much better though. It was finally a flesh and blood cock in my little mouth. The handsome man continued to gently stroke my back and neck as I sucked on him. He was moaning my name and telling me I was making him feel so good. He even called me baby.

I sucked and slurped on that hard cock. I would take my mouth off it occasionally and just run my tongue around the head, as if it was the last ice cream cone I would ever eat. I could tell he really enjoyed that. I would take him back in my mouth and slowly work my lips back down as far as I could. I wasn't able to get more than about 5" down my throat, but he never complained. I played with his big heavy balls as I sucked him. I imagined they were full of cum for me.

"Oh, Karlie. That feels so good sweetie. This is the best, baby doll."

I moaned around his hard cock when he called me that. He placed his hands on the back of my head and helped guide my lips up and down his cock. When I reached bottom he gave me a little nudge trying to get me to go further. I was afraid of gagging, but I didn't want to disappoint him. I tried to get a little bit more but he was just too thick. I felt myself gagging and my eyes were watering. I quickly backed off.

"I'm sorry. It's just too thick!" I sputtered.

"Mmm, don't worry baby. I'm sorry to push you. You were doing just fine." He reached under my chin and pulled me up a bit before he kissed me again. I loved that. When we broke our kiss, I resumed sucking that hard cock.

I sucked for another couple minutes when I felt him begin to tense up. I was so happy. I knew I was going to make him cum! He put his hands on the back of my head again.

"Ah, baby. That's so good. Here it comes," he moaned. He tensed up even more and I felt the head of his cock begin to throb on my tongue. All of a sudden he erupted in my mouth. I kept sucking just the head as jet after jet entered my mouth. I was trying to swallow some, as it just kept coming. Finally, he stopped. I pulled my mouth off the head and realized I still had about a tablespoon in my mouth. I swirled it around on my tongue, savoring the taste of it before swallowing it down. It definitely tasted different than my own.

I looked up to see him looking at me with a smile on his face. I smiled back at him.

"Was I good," I sheepishly asked.

"Good? You were great baby. Did you enjoy it?"

"Yes. I did. I loved it. It was even better than I thought it would be."

"Come back up here." He reached down and pulled me back up on the couch with him. He quickly kissed me. His hand was stroking my leg again as we kissed.

"My, you're excited." He laughed. I looked down to see that my clitty was making a very prominent bump in my tight black dress.

"Yes. I am," I blushed.

He reached for the wine bottle and poured us another glass. We sipped and talked about what we had done. He asked me if was comfortable with it. I told him I had been afraid that I would feel weird afterwards, but I actually felt really happy. I had made him feel great. He smiled.

"Would you be comfortable going further tonight?"

"Yes. I would." I wanted that more than anything and I told him so.

"Okay, good." We finished our wine and he stood up and took my hand. He led me upstairs to his bedroom. When we got there he took me in his arms and gave me another kiss. He turned me around and had me kneel on the bed. I felt him pull my tight dress up and I felt the cool air on my little ass. I looked back to see him kneel behind me. He placed his hands on my smooth ass and began to kiss my cheeks. I felt him pull my thong to the side. My little clitty finally found a bit of relief as he did.

I felt his hand wrap around it as he simultaneously ran his tongue across my tight little hole. I groaned and arched my back.

"Richard, that feels so good."

"I'm glad baby. I want you to feel good too." His tongue dove back in and began to probe my hole. I felt like I was in heaven. I laid my chest on the bed and crossed my arms in front of me as I laid my head down. I relaxed and enjoyed what he was doing to me. I couldn't believe how good it felt. He kept telling me how sexy I was and how much he wanted me.

I felt a cool liquid being dripped down my smooth crack. The fingers spread and then began to massage the liquid around my hole. One finger began to slowly enter me. I had penetrated myself too many times to remember, but having someone else do it was a new experience entirely. Soon I could feel the knuckles of his hand as he had buried his entire finger in me and worked it around inside. He continued to treat me with the sweetest comments.

I felt myself began to relax from his efforts. He began to work a second finger in me. His fingers were much thicker than mine and I felt myself stretching. I was still laying on the bed as he finger fucked me.

"I'm going to use a toy on you. Is that ok?"

"Mmmhmm." I replied.

I felt the hard tip of a dildo be inserted in my tight little hole. I arched my back as it entered me. He began to stroke it in and out. Damn it felt good. I felt like I was relaxed. I looked back over my shoulder at him.

"Baby, are you ready for me?"

"Yes, Richard." I nodded.

He stood up and finished undressing. I watched as he unwrapped a condom and put it on. He quickly lubed his big cock up.

He placed his hands on my slender hips and pulled me to him slightly. I felt his cock slide gently along my smooth ass crack. It was well lubed, and moved with very little friction. The soft spongy head was circling my little gurl hole. He moved into the center and it felt him slowly begin to apply pressure. I had felt like I was pretty loose, but the head of his cock was slightly larger than the dildo he had been using. In fact it was larger than any toy I have ever got inside me.

The pressure continued to build.

"Just relax baby. It'll be fine."

I nodded my head in response. I closed my eyes and concentrated on relaxing. Without warning, the head suddenly popped past my tight little ring, and he was inside me. I moaned softly.

"Ah." I groaned.

"Yeah. Me too." He agreed.

He continued to push softly into me. He paused occasionally to allow me to adjust to the sensation. I felt fuller than I had ever felt. Just when I felt I couldn't take any more, I felt his hips against my ass. He was all the way in me.

We stayed like that for a minute or two before he slowly began to pull back out. He began to slowly fuck me. I had experienced toys many times, but this was the best feeling I ever had. I loved having his strong hands hold my hips as he pumped inside me. I had finally found what I had been wanting.

I realized my clitty was painfully hard. Everything that had happened tonight added to his big hard dick inside me had me so turned on. I reached my hand back to touch myself. He noticed what I was doing and he reached down to push my hand away.

"Let me do it baby." I moaned and nodded my head and in agreement

I felt his large hand wrap around my hard clitty.

"Oh, Richard, it feels so good." I felt myself tense up. My clitty jerked in his hand and I shot my gurl cream. He pulled his hand back out and brought it to my face. It was covered in my cum. I began to lick his hand clean. It was interesting comparing my own cum to the generous load he had fed me earlier.

I was relaxed even further by the orgasm. He used this to his advantage as his paced quickened. I loved the sensation and the sound of his hips meeting my ass as he fucked me.

"Oh, baby. Your tight little hole feels so good. I'm going to cum."

"Please, can I taste it again?"

"Sure." He pulled out of me. I felt so empty, but my desire for another taste of his hot cum was all I could think of. I slid off the bed like a little porn slut and knelt in front of him. I watched as he yanked the condom off. I quickly took him in my mouth. His cock was covered with a wonderful, slimy layer of pre-cum. I took his smooth balls in my hand as my mouth worked up and down his hard shaft.

I looked up at him as I sucked. Being able to see him as I sucked really drove me wild. I moaned as I throated him.

"Karlie, baby. I'm going to cum."

"Mmm," I moaned.

I felt his cock begin to throb. I felt a little blast hit my tongue. It wasn't as big as the first load but I quickly gulped it down like a good gurl. I licked and sucked him until he went limp. He reached down to pick me up. He gave me a long, lingering kiss.

"Would you like to stay here tonight my dear?"

"No, I better go home. I have some things I need to take care of in the morning. I'll take a rain check though."

"Most certainly. I hope this will be the first of many meetings we share." He smiled sweetly.

"Yes me too." I had adjusted my clothes and we walked back to the entry.

He told me good night and gave me another long tender kiss. I walked out of his big house and quickly to my car. On the drive home, I replayed the evening's events in my head. It had been so good.

When, I made it home, I poured another glass of wine and drew myself a warm bath. I realized my little pussy was sore when I sat down. I guess I would get used to that. I had gotten my first taste, and I had loved it. I couldn't wait to do it again.

I was laying there with my eyes closed when my phone beeped. I picked it up and saw it was a text from Roxanne.

"How was it?" She asked.

I quickly filled her in on the details.

"Good for you gurl. That sounds wonderful. I won't keep you, I just wanted to make sure you had a good time and made it home safe!!"

I texted her back thanking her for all her help and support. "Don't mention it!" She replied.

After my bath, I put my usual pajamas consisting of a silk slip I had gotten from mom and a pair of suntan sheer to waist pantyhose. I was still thinking of being on my hands and knees getting fucked when I fell asleep.