Connie Goes to College Ch. 02

Disclaimer: The following story is not intended for minors. Any resemblance to actual persons is purely coincidental. 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 my stories that are a combination of true life encounters and fantasy.

Thanks for reading my story! My name is Connie and I am a 40-something transgender woman. To me there is nothing more exciting than taking a long bubble bath, shaving from head to toe, carefully applying makeup, selecting the right outfit for the day/evening, and going out to take on a new adventure. The following is a continuation of an adventure that really changed my life.

I had went out on Halloween dressed as Elvira with the help of Lynn, one of my best friends from high school. We ended up at a bar downtown and had a really good time drinking and dancing until closing time. I ended leaving the bar with one of the bartenders, named Jeff. It turns out he was bisexual and has a thing for cross dressers. When we got to his place we started making out on his couch and I ended up giving him a blowjob, my first of many in the months to come!

I fell asleep on the couch with my head on Jeff's chest. When I woke up a few hours later, my head was hurting like hell and I still had the taste of Jeff's cum in my mouth. Jeff started to wake up and said, "Hey sexy, let's head to the bedroom!" By this time the alcohol was wearing off and I was starting to feel guilty.

"Maybe I should be heading back to the dorm", I responded. "I don't feel so good and need to get out of these clothes." Jeff looked a little disappointed, but he didn't press the issue. He got dressed and we went outside to his car. Again he was the gentleman and opened my car door for me, but I behaved myself this time. Jeff dropped me off at my dorm and I was able to get back to my room without incident. It was around 6:00 AM and everyone was still sleeping. My roommate was in his bunk snoring away, so I quickly changed and ran down to the bathroom to remove the makeup. I slipped into bed and slept until early afternoon, dreaming about what had just happened and wondering if I could ever do it again.

The following week I had trouble concentrating. All I could think about was Jeff, but I also felt confused. A couple of nights I fell asleep jacking off while replaying that magical night in my head. I continued to wear my panties and pantyhose under my male clothes whenever I could, but I had to be careful my roommate didn't catch me. I started to notice that I only thought about Jeff when I was wearing something feminine. And the desire to get dressed from head to toe again was really starting to get strong.

I finally ran into my friend Lynn she asked me if I had a good time on Halloween? I told her it was fun, but I drank too much. Then she started asking me some weird questions about how I liked dressing up like a woman and if any guys hit on me. I was embarrassed and didn't know what to say, so I just kind of blew it off. Then she said something that really made my heart stop, "It looked like you and that bartender were having a pretty good time!"

"What do you mean?" I stuttered. She went on to explain that she was in the parking lot with the guy that picked her up at the bar and saw me and Jeff kissing next to his car. My face was totally red and I was speechless. For the next hour or so, Lynn and I had a heart to heart talk and I basically admitted my fetish for women's clothes and my confusion about my attraction to men. She was very understanding and really tried to help me understand my true feelings. Lynn also said she was willing to help me explore my feminine side.

The next day we headed off to Goodwill again to find me some more clothes. I found a decent blonde wig, a few more pairs of shoes, and some jewelry. Then we stopped at the drugstore again, but this time to get me all the makeup I needed, pantyhose in multiple shades and some more press-on nails. I spent a small fortune in there and wasn't sure how I was going to afford my meals the coming week.

We went back to her room and she informed me her roommates were gone for the weekend. This gave me a chance to try on my new purchases and she helped me practice putting on makeup. I found myself talking to Lynn about fashion, makeup, and men, just like two girlfriends. The day went so fast that I didn't want it to end.

Lynn and I started hanging around each other more often. She was like a big sister to me and a very dear friend. She also kept teasing me about Jeff and said I should call him. I explained to her I didn't think of guys that way unless I was dressed, but I didn't tell her how many times I fell asleep wearing pantyhose, masturbating and fantasizing about being with a man. Lynn finally convinced me that we should at least go say hi to him.

So the next Friday we made plans to go out and have a few drinks. We got to the bar where Jeff worked early, so it was still pretty quiet. He was behind the bar and asked, "What can I get for you?"

I remembered he had only seen me as "Elvira", so I explained, "Hey Jeff! Don't you remember the 'Mistress of the Dark'?"

"Oh my god!" Jeff exclaimed. Then he got a big smile on his face and said, "I am so sorry I didn't recognize you without your makeup!" I was so embarrassed and looked around to see if anyone had heard him. "Who's your friend?" asked Jeff.

"This is my good friend, Lynn." I replied.

Jeff shook her hand and politely smiled. "It's nice to meet you," Jeff said.

"It's nice to meet you too! I have heard all about you," Lynn replied. I tried to kick her but she moved out of the way. I wanted to get up and leave at that point.

There was an uncomfortable moment of silence until Jeff looked at me and remarked, "I just realized that I don't even know your name. I know it's not Elvira!"

We all chuckled and Lynn offered, "You can call him Connie!" I was so embarrassed, but thought it was a cute name. Plus I wasn't sure if I wanted Jeff to know my real name. Looking back, I guess I thought he was going to blackmail me or something.

Jeff got us a couple of drinks and we made small talk in between him serving drinks to other customers. I excused myself to go to the bathroom and when I got back I could tell Lynn was up to something. She asked me, "What are you doing Sunday night, Connie? Jeff has the night off and was wondering if you wanted to watch some TV at his place?"

I couldn't believe she just set me up like that, but I was very intrigued. She had the whole thing figured out and was going to help me transform into "Connie". Her roommates would be out of town until Sunday night, so I could get ready at her place.

Sunday finally arrived and we spent nearly two hours getting me ready for my big date. I removed all the hair from my body again and Lynn had me put lotion all over myself. My makeup was a little more subtle than Halloween and I wore my new blonde wig. Lynn chose a simple black skirt with a floral blouse for me. Off-black pantyhose, bra, panties, jewelry, fake nails, and black pumps completed my outfit. Lynn finished by spraying some perfume on me.

I looked in the mirror and was very pleased with the transformation and maybe a little excited too. Lynn also noticed and teased my about the "tent" in my skirt, "A girl can't go out in public like that!" I excused myself to the bathroom and tried to hide it the best I could. Lynn let me borrow one of her purses, filled it with my 'supplies' for the evening including lipstick, powder, blush, driver's license, mirror and tissue. She even snuck a few condoms in there.

We had to sneak outside where Jeff would be picking me up. I was just praying that nobody would see me. I spotted Jeff's car and made a dash for the passenger door, turning to thank Lynn on the way. Lynn shouted, "Don't do anything I wouldn't do!"

I didn't wait for Jeff to open my door this time and jumped right in. He looked me up and down and commented, "Wow Connie, you look great!" I proceeded to get goose bumps all over and attempted to smooth out my skirt. He placed his hand on my knee as we drove off.

The drive to his house seemed to take forever. I couldn't wait to get inside so I could relax. "Do you want anything to drink?" Jeff offered.

"Something strong and keep them coming!" I replied. He laughed and suggested a Gin and Tonic. It was just what I needed and it started to calm my nerves. Jeff invited me into the dining room and I noticed the table was set for two. There were also candles and some simple flowers in a vase. I could also smell something Italian cooking in the kitchen. I was really surprised and didn't realize he planned on making dinner for us. Jeff was such a romantic!

We sat down and had a wonderful meal of Lasagna, bread sticks, a salad and a nice bottle of red wine. We talked about all sorts of things and I really started to feel at ease with Jeff. He was a perfect gentlemen and made me feel very pretty and feminine.

After dinner we went to the living room and he made us some more drinks. "Are you trying to get me drunk and take advantage of me?" I asked.

Jeff laughed and said, "Only if you want me to!" He rented a movie so we sat on the couch together to watch it. I could barely focus on the screen as we sat there with his arm around me. I wanted so bad to kiss him but didn't want to make the first move. After about a half hour I 'accidentally' let my hand slip to his crotch and felt a raging hard on. I giggled like a school girl and Jeff asked, "Do you like what you have found?"

He then leaned over and started kissing me very gently. Our tongues found each other and soon we were rolling all over the couch. I wanted so bad to give him a blow job again! Jeff suggested we go to his bedroom where we would be more comfortable. He took my hand and we walked down the hall. When we got to the bedroom, I told him, "Jeff honey, let me undress you!" I slowly took off his shirt and kissed his hairy chest. Then I unbuckled his belt and unzipped his pants. Jeff kicked off his shoes and got on the bed wearing nothing but his underwear.

I got on the bed next to Jeff and started kissing his chest again. I ran my red nails through his chest hair and looked up at him, trying my best to be sexy. I kissed and licked his nipples, slowly working my way down to his crotch. I kissed his cock, leaving a lipstick print on his underwear as Jeff starting to moan. "Oh Connie, you are such a sexy girl!"

"Jeff, I love being a sexy girl for you!" I replied as I looked up at him and smiled.

I slowly removed his underwear and starting sucking his dick like there was no tomorrow. "Slow down, baby!" Jeff whispered. "We have all night." I continued to suck him, trying to pace myself. I ran my tongue all over the head and shaft, getting to know every inch of his cock. He was circumcised and about 7 inches long. I found myself really enjoying the feel of a hard warm cock in my mouth and could taste his sweet precum.

I kept bobbing up and down on his hard member as my hair and earrings rubbed against my cheek. Before long, Jeff started to tense up a little and announced, "Oh Connie baby, I am going to cum!" Just as I did the first time, I closed my eyes and waited for my reward. Jeff started to cum pretty heavily, but this time I seemed to enjoy the taste more. I swallowed all I could and continued to suck on his cock. When he was finally done, he gently pulled out of my mouth.

"Baby, you are becoming one great cocksucker!" said Jeff. "You can do that anytime you want. I might have to turn you into my personal cum whore!"

I didn't know what to make of his dirty talk, but I kind of liked it. All I know is that I really enjoyed pleasing him. I laid on the bed next to Jeff who was completely naked, while I still had on all my clothes except for my shoes. I wanted to stay dressed so I could continue feeling like a woman. We rested awhile and then Jeff got up to use the bathroom. When he came back I noticed he was hard again. I grabbed his dick and we started kissing again. "I want to suck you again, Jeff" I pleaded. I just wanted to get that cock in my mouth again and started feeling kind of naughty.

Then Jeff whispered in my ear, "How would you like me to make you a complete woman tonight, Connie?"

I didn't know what to think and was a little bit scared. I had played my anus in the shower, but never really had anything inserted inside. "Don't worry baby. I will take it nice and slow and I promise not to hurt you," Jeff assured me. "Besides, I bet you will come to love it and need it all the time! Now be a good girl on get on all fours."

Jeff leaned over to his night stand and removed a condom and a tube of KY. I had previously explained to Jeff over dinner that I felt uncomfortable getting undressed. He said he understood how the clothes helped make me feel feminine. So he pulled my skirt over my back and pulled down my pantyhose and panties.

"Very sexy panties!" he remarked. "I bet you would look great in some sexy lingerie." Jeff proceeded to squirt some KY around my hole and I jumped from the feeling of the cold gel. He then massaged it all around my anus and slowly stuck a finger inside. He added more KY and continued loosening me up and eventually got two fingers inside. I started to feel more comfortable as I squirmed around the bed.

Then I heard Jeff open the condom wrapper and I knew what was next. I put my head down and buried my face in his pillow. I felt the head of his dick start to enter my hole and I screamed out in pain. It is a good thing the pillow muffled the sound. "Are you alright, Connie?" asked Jeff.

I just mumbled something and tried to stable myself on my knees. He backed off a little and tried again. This time he made it further, but it felt like my ass was on fire! I heard him squirt some more KY back there as he continued to work his cock inside me.

"Damn baby, you are so tight!" Jeff exclaimed. After what seemed like an eternity, I felt Jeff's thighs resting against my cheeks. I tried to relax as he started to thrust his cock in and out of my ass. Jeff started to pick up the pace and I started to enjoy the feeling of having his dick fill my ass. But that feeling didn't last long as the pain returned and I just wanted him to stop. Just when I didn't think I could take anymore, Jeff drove his cock deep inside me and I could tell he was having a wonderful orgasm. He was sweating and breathing hard and finally pulled out of me. I collapsed on the bed and turned to see him holding the condom full of his cum. "Well Connie, I guess you are a woman now!"

He went off to the bathroom to clean up and just laid there thinking how glad I was that I satisfied Jeff, but I wasn't sure if I was going to enjoy anal sex. While it felt good at times, I didn't know if I was going to get used to the pain. Before Jeff returned, I drifted off to sleep.

I awoke a few hours later to find Jeff and I in the 'spooning' position. As I repositioned myself, Jeff began to stir. He started to move closer to me and I could feel his dick began to get hard as he rubbed against my butt. "Good morning sexy!" said Jeff.

"Hey baby," I replied. "I am sorry I passed out on you. All the wine and liquor really made me tired."

"No problem. I was watching you sleep for awhile and you looked so darn cute laying in my bed!"

I was so embarrassed and I wondered what I looked like now. I was certain my makeup was a mess and my clothes were all wrinkled. "I need to use the bathroom and then I should probably be getting back to the dorm soon."

"Why don't you stay for breakfast and then I will give you a ride home?" asked Jeff.

"That's sounds like a great idea! I need to change out of these clothes before we go though," I explained. I had brought a change of boy clothes so that I could get back to my dorm room.

"Sure, no problem. But why don't you freshen up a bit and stay dressed for breakfast?"

I guess Jeff wasn't crazy about seeing me in male drab, but I didn't mind. The more I could stay dressed the better as far as I was concerned. I felt sexy and very relaxed when I was dressed. I excused myself to the bathroom and proceeded to touch up my makeup the best I could. I straightened my hose and tucked in my blouse. I found my pumps and put them on as I sat on the edge of the bed. I caught a glimpse of myself in the mirror and saw a sexy young woman. I needed a little work, but "not too bad" I thought.

I walked into the kitchen and Jeff was standing there in a tee shirt and a pair of loose fitting shorts. When he heard the sound of my heels clicking on the floor, he turned and smiled. "Wow, that was quick. You look great!"

"Thanks! You don't look so bad yourself." I looked down and noticed Jeff was getting excited again. "Is that my breakfast you have down there?"

"I was going to make us some eggs and toast, but you can have some of this if you want," replied Jeff as he grabbed his crotch.

"Yummy!" I said as I licked my lipstick covered lips. I don't know what was happening to me, but all I could think about was cock. I rubbed Jeff's throbbing member through his shorts and I could tell he didn't have on any underwear. I sank to my knees on the kitchen floor and pulled his shorts down to his ankles. His cock sprang free and almost hit me in the chin.

I leaned forward and wrapped my lips around the head and began licking the tip. I inhaled deeply and I could smell his musky manly scent. Jeff braced himself against the sink as I continued to devour his cock. Then I tilted my head and did the best I could to lick and suck his hairy balls.

"Oh my God, Connie! That feels so good. Suck those balls, baby!" cried Jeff.

I continued to suck his balls and lick his sack, covering them with lipstick and saliva. After a few minutes I went back to sucking his cock. It felt so warm in my mouth and I wanted him to cum so bad. A couple of times I tried to take too much in my mouth and started to choke. By now my eyes were watering and my mascara was running down my cheeks. The desire to please Jeff was very strong as I continued to give him the best head I could.

Jeff began to encourage me by shouting, "I am getting close, baby! That's it, keep sucking! I love that sexy mouth of yours, you little cocksucker!" Then Jeff's whole body began to shake and he started to cum in my mouth. I felt the salty liquid hit my tonsils as I tried to swallow as fast as I could. Some of his cum leaked out the corner of my mouth onto my thigh.

Looking back on this day, I think this is when I really started to enjoy the taste of a man's cum. I had no idea it would turn into such a fetish later on. I also surprised myself that I had such a desire to suck a cock without being drunk. Maybe there was alcohol still in my system, or maybe I was finally doing something that felt natural to me.

After Jeff regained his composure, he pulled up his shorts and pulled me tight and kissed my cheek. "Maybe I can return the favor?"

As horny as I was, I really didn't want Jeff to blow me. It is hard to explain, but to this day I really don't like for guys to suck me. I guess it's because I try desperately to be as feminine as possible. I explained this to Jeff and he seemed to understand.

Jeff proceeded to make us some breakfast. We sat down at the kitchen table and Jeff told me a few funny stories about things that happened at work. A couple of times he had me laughing so hard my stomach hurt. I was thinking how lucky I was to be spending time with someone so kind, good looking, and funny.

After breakfast I excused myself to the bathroom where I changed clothes and washed off my makeup. I had trouble getting all the mascara off, but I didn't want my roommate to suspect anything. It was nearly 10:00 AM and Jeff dropped me off at my dorm. "Thanks for a wonderful evening!" I said as I got out of his car. I felt a little awkward, but I didn't think a goodbye kiss was appropriate.