Connie Goes to College Ch. 04

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures.

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My freshman year was really turning out to be a pivotal time in my life. All of my suppressed feelings over cross-dressing and whether or not I was gay came to the surface with a little help from my best friend Lynn and my new boyfriend Jeff. Yes, I truly had a boyfriend in Jeff. He was kind, romantic, good looking, understanding and a true friend also.

I admit, there were plenty of times when I still felt confused, ashamed, guilty, and dirty, but those feelings seemed to go away when I put on my makeup, panties, bra, pantyhose and sexy shoes. I just wish I the internet was more mature in those days. I know it would have been extremely helpful for me to know there were others out there like me. Not to mention access to the wonderful world of online shopping and dating!

That first year in college went by so fast. I worked hard to get decent grades and really stayed on top of my school work during the week. On the weekends all I looked forward to was seeing Jeff, so I rarely went home either, except for holidays. He had given me a key to his place so I could get there Saturday evening and transform into 'Connie' before he got home.

With a lot of help from my dear friend Lynn, I had built a pretty decent wardrobe that I kept in Jeff's spare room. When I had some extra money we would find some things on sale at the mall. Occasionally Jeff would surprise me with some panties or lingerie. I also had fun experimenting with makeup and became fairly good at achieving a feminine look.

Most weekends followed the same routine. I would get to Jeff's place early Saturday evening, get all dolled up, have a few drinks, and wait for my 'man' to come home. Since it was already fairly late and we hadn't seen each other all week, we were either rolling around on the couch or on the bed within a few minutes. All it would take is a few tender kisses from Jeff and I would be ready to tear his clothes off!

Our Sundays were spent taking it easy around Jeff's place. We would start with a nice breakfast, maybe read the paper, watch some TV, etc. I would even help him clean, doing some vacuuming and dusting, washing dishes, cleaning bathrooms, and other little things around the house. Sometimes Jeff would leave for a bit to run some errands and I would stay behind, trying on clothes or playing with my makeup. We would usually have sex two or three times on Sunday before I had to change back to boy mode and get back to the dorm. Sometimes I would go back late Sunday, but many times I found myself leaving early Monday morning.

At this point in my cross-dressing days I still didn't have the courage to venture outside (other than Halloween). Jeff and I talked about it a few times, but we both agreed that it just wasn't a good idea in a small college town. Then one Saturday night, Jeff surprised me with an idea that would help take me to that next phase in my cross-dressing life - 'dressing in public'.

It was a typical Saturday night one weekend in January. I was all dressed up and waiting for Jeff to come home from work. I looked in the mirror one last time and was feeling very horny when I heard the back door open.

"Hi honey, I'm home!" shouted Jeff. I was our silly little joke, but I never got tired of it. I had a cold beer waiting for him as he came into the kitchen. I greeted him with a big kiss and in return he hugged me and squeezed my butt.

"Hey baby! I missed you so bad," I purred into his ear.

"I missed you too! I have a big surprise for you this weekend. Stay right there, I'll be right back."

"I can hardly wait!" I replied.

Jeff went back to the bedroom for a few minutes, and then returned with a big smile on his face. He took hold of my hand and said, "Come here. I have something I want to show you."

Jeff pulled me back to the bedroom and lying on the bed was a black sweater dress and a pair of sexy knee high black boots. I was so happy that I had tears in my eyes. "I love it! I have wanted an outfit like this for awhile!"

"I know. Your friend Lynn told me." Jeff went on to explain he had got in touch with Lynn and asked for her help in finding me a special outfit. I know he must have had a hard time finding the boots, because my feet aren't exactly small. I had seen the dress when Lynn and I were shopping and I remember confiding in her how I love the look of a sweater dress and nice boots. There was also a small bag that contained all the jewelry I needed to match the outfit, including big silver clip on earrings, a silver necklace, a couple silver rings, a silver watch, and silver bangle bracelets. Some of the items were brand new, but I recognized a few pieces that belonged to Lynn.

"Jeff, you really out did yourself. This is so beautiful and I can't wait to wear it!"

"This is only part of the surprise. Tomorrow we are going out to dinner and a movie," Jeff explained.

"But I thought we both agreed that it wasn't a good idea?" I asked nervously.

"I have it all worked out. We'll get up early and take a little road trip to the city. I have a hotel room booked for us and dinner reservations at this really nice restaurant."

"Wow, I can see you really have put a lot of thought into it." I was still nervous, but excited too. "We better get to bed if we have to be on the road early."

I quickly changed into my nightgown as Jeff finished his beer. It didn't take long before we were under the covers with my head between his legs sucking on his cock. Jeff came pretty quickly and we both agreed to try to get some rest in preparation for our little getaway.

Morning came pretty quickly and I awoke to the smell of coffee. Jeff was already awake reading the paper. I was a little surprised he didn't wake me up, but he said I needed my rest, so I headed for the bathroom. I first shaved my face real close and then got my enema bag out from under the sink. This was something Jeff taught me to do so I would be nice and clean for him. After rinsing a few times, I got in the shower and shaved the rest of my body. When I got out of the shower I dried off and put some nice smelling powder all over myself before starting with the makeup. I had experimented with a simple look several times during my Sunday afternoons with Jeff. I called it my 'housewife' look and decided it would be appropriate for the three hour ride to our hotel. It took me about an hour to finish my makeup, finishing off with a subtle shade of pink lipstick.

Next I had to decide on my outfit for the day. I started with my panties, bra, tan colored pantyhose and a full length slip. To give my bra that natural look, I had experimented with water balloons and really liked the way they felt, adding weight to my chest and providing some movement as well. I loved to parade around like this while deciding what to wear as my 'boobs' jiggled around. Back then I would have never considered something like jeans or Capri pants, it had to be a dress or a skirt. I wanted to dress casual, so I chose a long skirt and a frilly white blouse. Simple black pumps with a moderate heel completed the outfit. The only thing left was the wig. I only had a few to choose from, so I decided to wear the short blonde bob style on the trip and pack the longer blonde frosted one for dinner and the movie.

I continued to pack my suitcase with my new outfit, makeup, and everything else I would need for the trip. It looked like I was packing for a week's vacation. Jeff came into the bedroom and saw I was almost ready and decided he better jump in the shower. Soon we were all packed and ready to get on the road. Jeff put our bags in the trunk and opened the passenger side door. There is something about sliding into a car seat while wearing a dress or skirt that is a real turn on for me.

As we drove, I playfully flirted with Jeff, pulling my skirt up over my knee and crossing my legs. Occasionally he would rest his hand on my leg or rub my knee. It turns out that was another big turn on for me and I get goose bumps just thinking about it. I think I was hard during the whole ride there. Another thing I enjoyed was using the fold down mirror to apply lipstick and powder my face. I am sure that was driving Jeff crazy, but if it was he was too polite to say anything.

We arrived at our motel early that afternoon. It wasn't anything fancy, but it was one of the nicer chain motels, if I remember correctly. Jeff went inside to register and returned with the key. We pulled around the side, got our luggage and went up the stairs. Jeff took my big heavy bag of course, being the gentleman he was. I felt like we were just your everyday couple going on vacation together. The nice thing was I didn't have to worry about running into someone I knew, but was still a little nervous when I came in contact with anyone. I would just avoid eye contact and keep walking. Maybe not the best way to act in public, but I think I have come a long way since then.

We got to our room and quickly went inside. As soon as I set my things down, Jeff tackled me onto the bed. We rolled around, kissed and tickled each other for several minutes. Jeff had his hands all over me and soon my skirt was pushed above my waist. He continued to rub my legs and squeeze my little clitty through my pantyhose. Then he flipped my over on my stomach and pulled down my pantyhose and panties.

"You little tease! I am going to fuck your little brains out," moaned Jeff.

"Oh yes! Please screw me, baby," I replied. I was really turned on by Jeff's aggressive moves and dirty talk.

Jeff removed his pants and underwear as I got into the traditional doggy position. I wiggled my ass in the air, trying to make him want it even more. He found the KY jelly in my purse and jumped back on the bed. I turned away as he applied the cold substance to my behind, causing me to jump a little. Jeff laughed and proceeded to line his cock up with my hole. He entered me a little quicker than normal and started pounding away. I could feel his balls slapping against me as his pace continued to quicken. With one hand he reached around and massaged my aching dick bringing me close to orgasm.

I pushed back to meet his thrusts as he slowed down and tried to push in as deep as he could go. Then Jeff shouted, "Oh my god! I am cumming. Oh shit, that feels so good!"

It was at this point I felt something odd inside of me, something I never felt before. It was a warm feeling deep inside my gut. As Jeff pulled out and rolled over, I too collapsed on the bed. I quickly finished myself off and sprayed all over my thighs and skirt. I looked over at Jeff and that is when I realized he didn't use a condom. We always used a condom and never really talked about going bareback. I didn't think I had anything to worry about with Jeff, but I still wanted to be careful.

"Jeff, why didn't you use a condom? I can't believe you did that!" I exclaimed.

"Sorry Connie. I guess I got carried away. But don't worry, I have never done that with anyone else and I had a blood test a few months ago."

"I know I can trust you Jeff, but it still scares me. I hear too many stories of people catching diseases from sex." We talked about it for awhile and I calmed down after the initial shock. I really did trust Jeff. He was a little older than me and had really showed me a lot about sex and pleasing each other. I guess I did enjoy it too and it felt pretty sexy.

As I lay on the bed resting, I could feel Jeff's seed leaking out of me. At that point I was glad I cleaned myself real well before we left. But one ritual I had come to enjoy was removing my lover's condom and cleaning his cock with my tongue, occasionally enjoying some of the cum in the condom. Pretty often Jeff would get hard again and before you know it I was giving him a blowjob to completion. I was such a good little girlfriend! I excused myself to the bathroom so I could clean up. I had my own come all over me and Jeff's starting to leak down my leg.

I got out of my clothes and started cleaning up for the evening. Jeff went out to get us some beer before going out. I knew I was going to need something to calm me down. I was excited, but still pretty nervous.

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To be continued...

I hope you have enjoyed my early attempts to share some of my memories. Feel free to leave a comment or send me an email.