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Connie Goes to College Ch. 01

By: cmorehead



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. 

*

Let me start by introducing myself. My name is Connie and I am a 40-something transgender woman. I live part of my life as a man, but I enjoy spending most of my free time practicing the art of female illusion. 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.

I have been a fan of erotic stories for many years, so I thought I would contribute a few myself. Let me start with an early adventure when I was much younger and very inexperienced.

I first discovered the joys of cross-dressing in my early teens, trying on my sister's clothes and pantyhose. It wasn't until I got to college that I was able to enjoy the freedom of getting dressed en femme. I kept a small stash of panties and nylons hidden away in my closet and would wear them to classes whenever I could. The feeling of nylon kept me in a constant state of arousal.

As it turns out, my freshmen year was going to be the beginning of many wonderful experiences for me. Halloween was fast approaching and I always wanted to take the opportunity to dress up in some feminine costume. My circle of friends that first year consisted mostly of guys and girls from my high school. So one night after classes I was hanging around a few of the girls and we started talking about the Halloween parties that were planned in the dorms. I started "hinting" that I had no idea what my costume would be, and we started tossing around different ideas. Everyone mentioned all the typical costumes like ghosts, ghouls, witches, cheerleaders, pimps and hookers, etc. 

During one point in the conversation, I mentioned how much I really liked Elvira and how sexy she was. I couldn't believe my ears, but my good friend Lynn suggested that I dress up as Elvira! Trying to hold back my excitement as best I could, I of course pretended that it would never work. She eventually convinced me that she had a few ideas on how to make me look like Elvira and how much fun we would all have. So we decided that we would go to the local Goodwill store that weekend and find the necessary items.

As you can imagine, it took forever for the weekend to come. I went over to Lynn's dorm room early on Saturday and we headed off to town. At the Goodwill store we had a lot of fun looking through all the clothes and shoes trying to find something to fit me. Lynn decided she was going as a "Flapper" girl and found a really great dress and some gaudy cheap jewelry. Finding things for me was a little more difficult, but we finally found a long black dress and some black high heels. It was a little embarrassing trying them on in front of her, but she really put me at ease with a few encouraging words.

After getting the bulk of our costumes at Goodwill, we were off to the drugstore. Here we found all the makeup she needed and the black pantyhose I would need. Yes, that was another embarrassing moment. To complete the costumes, we needed wigs, so we stopped at the mall on our way home. We were able to find a funky orange-red bob style for her and a long black one for me at one of those kiosks. They were a pretty decent quality and didn't cost too much either.

We finally got back to the dorms and Lynn offered to keep everything in her room. Halloween was still a couple weeks away and it couldn't come to soon. Finally, on the morning of Halloween, Lynn called and told me to meet at her room around 4:00 so we had plenty of time to get ready. She also told me to bring my shaving kit. When I arrived, her and her roommates were already getting dressed. She handed me a couple bottles of Nair and told me to go in their bathroom and cover my entire body from the neck down. I was to wait for 10 minutes and shower everything off. 

I got in the shower and proceeded to take a wash cloth and remove all the hair. When I was finished, I noticed she had laid out a bra, panties, and pantyhose. There was also a black robe hanging on the door. She peeked in the door and told me to shave very close and put everything on so she could start applying the makeup. I asked her if the bra and panties were necessary, and she said I needed a way to hold my breasts in place and a proper girl should wear panties. 

She had me sit down in front of the mirror and started to work on my makeup. She did an incredible job making me look very sexy with dark eye shadow, lots of mascara, blush, and bright red lipstick. After the makeup was finished, she placed the long black wig on my head. I still remember desperately trying to hide my "excitement" as her roommates teased me.

Then Lynn had me take off the robe and handed me a couple of water balloons for my bra. They felt so heavy and really jiggled when I moved. Next came the dress which I noticed Lynn had altered. She was very proud of the high slit she added to the dress which showed off my long legs. I put on my shoes and practiced walking in them awhile. Lynn added a necklace, clip-on earrings, and surprised me again with some sexy press on nails. Before we left, one of the girls loaned me a little purse to hold my lipstick, driver's license, and money. Lynn and her roommates were proud of their work and really wanted me to play the part. 

Soon we were all off to the party. I had a little trouble walking in the shoes at first, but quickly got used to them. The music was loud and the beer was flowing. I was very self-conscious about being dressed like this, so I stuck pretty close to Lynn. As the night wore on, more and more guys starting grabbing my butt and making lewd comments. I often wondered how many knew I was a guy and how many I fooled. I suppose more knew I was a guy than didn't, but I really started to loosen up and have fun.  I started dancing more, even though the heels started to bother me. The more I danced with Lynn and her friends, the more feminine I felt. Fortunately, I didn't run into many of my guy friends. The ones that I did see couldn't believe how good I looked, but I could tell they were a bit uncomfortable and didn't know what to say. I also ran into my roommate, but I realized I didn't tell him about my costume beforehand. He was really surprised it was me and couldn't stop staring, but I found it strangely arousing (more on him in later chapters). 

The party started to die out around midnight, so a group of us decided to head downtown to one of the bars. One of Lynn's roommates offered to drive even though it was just a few blocks away. Lynn and I sat in the back seat and she showed me how to apply my lipstick to keep it looking fresh. The bar was pretty crowded, but not as many people were wearing costumes. I felt a little out of place again, but Lynn quickly found us a table and I took a seat to rest my aching feet. Before I knew it, guys were buying us drinks and asking us to dance. Now instead of just dancing with Lynn and her friends, I found myself dancing with a few different guys, and I really started to enjoy myself. One guy who seemed like he had a few too many drinks even asked me to dance to a slow song. I could feel his hard on rub against my thigh and I had to do my best to hide mine. More than once I had to slip off to the bathroom and try tucking it away. I even practiced putting on my lipstick.

I glanced over at Lynn and noticed she was getting to know one of the guys better. I went up to her and whispered that she didn't have to worry about me and she should go for it. Before I knew it, most of the gang had either left the bar or were in the process of hooking up. Since it was almost closing time, the crowd was getting pretty thin, so I took a seat at the bar. The bartender came over and asked me what I was drinking. He was a little older, maybe 25 or so, tall and pretty good looking. I was feeling a little flirtatious, so I asked him what he recommended. He said, "a sexy girl like you should be drinking a mixed drink instead of beer from the bottle." He introduced himself as Jeff and said he had the perfect drink for me. He quickly mixed a few liquids into a shaker, poured it into a cocktail glass and said, "It's was on the house!" I don't know what was in the drink, but it was sort of sweet and made me warm all over. I had a few more and before long it was last call. By this time I had trouble sitting on the bar stool and still trying to play the part of Elvira. He noticed my predicament and offered to drive me home. Not wanting to walk all that way in heels, I quickly took him up on his offer.

I sat at the end of the bar while he closed up. I had trouble staying awake, but Jeff was done pretty quickly. Soon we were off to his car and he had his arm around me, helping me walk. When we got to his car, he offered to open the door for me, just as any gentleman would for a lady. As he reached for the door, Jeff got very close to me and I don't know why, but I put my arms around him and gave him a kiss on the cheek.

Jeff looked a little shocked and responded, "why you sexy little devil you!" He then proceeded to kiss me on the lips and I felt this surge of emotions running through my entire body. We began to make out right there next to his car. His hands were all over me and I could feel my pantyhose expanding. After about 10 minutes of heavy petting, he suggested we go back to his place. I was pretty drunk and horny, but up to this point, I had never been with a man. I told him I was embarrassed for kissing him, but I didn't think I was gay. He explained he was bisexual and had a thing for feminine guys and cross dressers. He put me totally at ease as he held my hand and explained what I was feeling was completely natural. Jeff promised we could just talk and he would take me home whenever I wanted.

I don't know why, but I felt very comfortable with Jeff. It was almost like he was an older brother, but I was attracted to him on some level. We drove to his house and I made myself comfortable on the couch. Jeff offered me a drink, but I thought I had too much already and asked for some water instead. He sat next to me on the couch and casually placed his hand on my thigh. Before I knew it, I was looking into his eyes and we started to kiss again. I did my best to kiss like a lady and I could tell he was enjoying it. 

I was getting very horny again and I just couldn't help myself. I started rubbing his crotch through his jeans. It felt so good to feel his hard on and I think I actually started to drool with lust. Jeff asked me if I wanted to give him a blow job and I think I barely said "yes" because I was so nervous. He told me not to worry and he would guide me. He stood up and took off his jeans. I got on my knees on the floor and stared at his white briefs with this raging hard on trying to get out. I kissed his cock through his underwear and then pulled them down to his knees as his cock sprang to attention. Jeff had an average size cock, but I was fascinated by how another guy's dick looked up close and slowly massaged it with my hand. 

Jeff rubbed my cheek and said, "go on baby, suck it like a lollipop"! That was all the encouragement I needed as I started suck the head and lick the entire shaft starting at his balls. For a beginner I thought I was doing pretty good and I felt my panties getting wet as I continued to suck Jeff's cock. Before long he starting moaning and I knew what was coming next. I was afraid to have him come in my mouth, but for some reason I just kept sucking. Then Jeff said, "Oh baby, I'm coming!" and I just closed my eyes and hoped for the best. I felt his cock explode as his balls tightened and the cum shot hit the roof of my mouth. I remember it tasted salty, and had a thick consistency. I almost gagged, but for some reason I just started swallowing it. He shot a few more squirts then pulled out of my mouth and sat down on the couch. 

As I sat there on the floor with the taste of Jeff's cum in my mouth, I felt ashamed, excited, sexy and somewhat confused. I also noticed my panties were completely wet as I must have cum quite a lot myself. I got off my knees and joined Jeff on the couch. He put his arm around me and we actually cuddled for awhile. Jeff assured me that I did a good job pleasing him and hearing that made me feel good. We ended up falling asleep right there on the couch, with my head on his chest and my hand on his crotch. 

(To be continued)

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.




Connie Goes to College Ch. 02



"I would love to do it again sometime!" said, Jeff. "How about if I call you and maybe we can do something next weekend?" 

" That would be great! I am sure Connie is free." I said, giving him a wink. I gave him my phone number and then headed for my room. When I got there my roommate was already gone. So I stashed my gym bag with "Connie's" clothes in my closet. I was glad I was alone because I needed to relieve some stress and take a nap.

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.



Connie Goes to College Ch. 03



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. 



In my last chapter, Jeff and I had just made love for the very first time and I was back in my dorm room all alone. I was still pretty horny from the previous evening, so I jumped in bed and started to play back the events in my mind. I reached into my panties and started to play with my little dick and it didn't take long before I came all over my belly. As I lie there catching my breath, I scooped up some of my cum so I could taste it. I had never really done this before, but after Jeff came in my mouth a couple of times, I was really curious. It seemed to taste ok and I remember it made me feel even more girly and naughty.

I was pretty tired after my date, so I decided to take a nap before my afternoon classes. I was rudely awakened around lunch time by my roommate, Andy. He and I got along ok, having not known each other prior to our freshman year. Andy was a jock and played on the Lacrosse club team. I on the other hand, was not very athletic and tended to keep to myself when I wasn't hanging out with my friend Lynn.

"I see you finally made it home!" said Andy as he dropped his books on his desk. "Did you have a hot date last night?"

"I guess you could say that," I replied. I could hardly tell him the truth and I was just hoping that I did a good job of removing all my makeup.

"Me and some of the guys are heading to the cafeteria for lunch. Do you want to join us?" asked Andy.

I remembered I was still wearing panties. "No, that's ok. I need to hit the showers and get ready for my classes. But thanks for asking."

Andy finally left for lunch and I quickly removed my panties and put on some shorts and headed down to the shower. I couldn't wait for my classes to end that evening so I could meet up with Lynn and tell her all about my night with Jeff. We ended up meeting for dinner in her cafeteria dorm and we got a table out of the way. She asked me all sorts of questions and insisted on getting all the details.

I told her that I really liked oral sex, but I wasn't sure about anal. I was still a little sore down there and worried I might be walking funny. Lynn comforted me by explaining that the first time she made love wasn't all that great either. We continued to talk about all sorts of things until the cafeteria was ready to close. She promised we would go shopping again very soon, but I would have to save some money first. I didn't realize how expensive it was trying to be pretty!

Over the next several weeks, Lynn and I continued to bond like two girlfriends. She really was my best friend in the whole world, and the only one besides Jeff that knew about Connie. I also continued to see Jeff on the weekends and was starting to build up quite a wardrobe that I kept in his spare room. In a later chapter I will convey some more adventures with Jeff, but first I want to take a detour to write about my roommate, Andy.

About halfway through the semester, I was in my room alone on a Friday night trying to catch up on some studying. My roommate Andy stumbled in around 3:00 AM after a night of drinking and trying to pick up chicks. He didn't have a steady girlfriend, but he managed to do ok. There were many times I would get kicked out the room for a few hours while Andy 'entertained' the ladies.

"Hey Andy! How's it going? Did you have a good time tonight?" I asked.

"Yeah, it was ok," replied Andy. "Me and some of my teammates went to a wild frat party. You should have seen all the chicks there, man!" 

"I have heard about some of those frat parties. I bet it was fun. Did you get lucky?" I asked.

"No. I thought I was doing real well with this one chick. We were kissing and I was feeling her tits," explained Andy.

"Well, what happened then?" I asked, getting a little curious. 

"Her friends wanted to go home and she just blew me off. Dang, I really thought I would at least get a blowjob!" said Andy as he rubbed his crotch.

I tried to look away but I could tell he was getting very hard as his dick strained against his jeans. "That sucks!" I said as I tried to empathize with him.

"No doubt, dude. I am so freakin' horny right now! I just really need to bust a nut" said Andy as he continued to look at me.

I was starting to get a little uncomfortable by his tone and pretended to start studying again. Andy sat on the edge of his bed and started to take off his shoes. "I have to run to the bathroom, Andy. My stomach doesn't feel so good" I offered. I just wanted to leave for a few minutes hoping he would take care of business and go to sleep.

"Maybe you could do me a favor?" whispered Andy. "Why don't you come over here and suck me off?"

"You have got to be kidding me? Why would I do that? I'm not gay!" I exclaimed.

"Oh really?" replied Andy. "Then why do you have girls' underwear and pantyhose hidden in your closet? If I remember correctly, you looked pretty convincing as Elvira on Halloween too. I bet you are one of those sissy boys!"

I stood there in shock. I couldn't believe my roommate was saying those things. I also felt betrayed that he would go through my belongings. "What the heck were you doing in my closet?" I shot back.

"It doesn't really matter. The fact is I bet I am right! So why don't you get your pansy ass over here and suck my dick, faggot!" demanded Andy. "If not, then maybe I will tell everyone on this floor that you are a little sissy that likes to wear girls' clothes." 

My mind was racing a mile a minute and my stomach really did start to hurt now. As much as I enjoyed being with Jeff, this was much different. I had never seen Andy like this and I was a little scared. I didn't want everyone knowing about my little secret and thankfully Andy had no idea how much more there was to my dressing up.

Andy pulled down his pants and underwear and sat down on his bed. He started to stroke his cock and I could see his precum starting to leak out. His dick looked slightly larger than Jeff's, about 8 inches long and fairly thick. He had a thick blonde bush and big hairy balls. 

"What are you waiting for you sissy? Start sucking this big cock!" said Andy.

I got on my knees between his legs and lowered my head towards Andy's cock. I could smell his musky scent from his crotch and the beer on breath as he layed back on the bed. Andy grabbed my head and thrust it on his dick. I gagged and tried to pull away, but he held my head firmly. My eyes started to water from the force of his cock in my throat and I think I was actually crying a little too. This wasn't something I was really enjoying, partly because I wasn't dressed up and partly because I was used to Jeff's tenderness.

Andy basically continued to assault my mouth and throat for the next ten minutes or so. I just wanted it to end as soon as possible, so I did my best to suck him and work my tongue over his cock.

"Oh my god! You are a great little cocksucker!" grunted Andy. "You suck cock better than most girls I know." 

Andy let loose of my head a little so that I could control the pace. I noticed his breathing was getting heavier as he called me all sorts of names.

"That's it you little sissy. Suck my cock you faggot cum whore! I can tell you are loving it."

I wasn't used to all the name calling and dirty talk, but I did start to relax and enjoy it. I guess part of was the fact that Andy really did have a nice dick, although I never really noticed before. And maybe a part of me liked the name calling in some twisted perverted way.

"I'm getting close, bitch. Keep working that tongue and you'll have your reward soon sissy!" panted Andy. 

I could tell he was getting close as I tried to get as much of his dick in my mouth as possible. Occasionally I would lick his balls and Andy would practically come off the mattress. As I put my mouth over the head of his dick and grab the shaft, I could feel Andy tense up and his balls retract. What happened next really surprised me and I swear is true. Andy cried out loud that he was cumming and I felt several violent eruptions in my mouth. I closed my mouth tightly around his cock and tried to swallow as fast as I could, but some of it actually came out my nose. I was literally chocking on his cum and came up for air. Another squirt hit me in the eye as I pumped Andy's cock to completion. A few more dribbles of cum landed on my hand as Andy collapsed on the bed. I didn't realize someone could cum so much and I don't think I have ever seen that much cum since.

I got up quickly and went to my closet looking for a towel or something to clean up with. Andy noticed the cum and my face and started laughing. "Look at the sissy with cum all over her face!"

I felt humiliated and proud at the same time. The cum in my eye was burning and my nose felt like it was full of snot. I got myself cleaned up as quickly as I could, but then I panicked because I was afraid half the dorm heard the whole thing. Andy mumbled a few more things and called me a few names before he went to sleep. I guess the alcohol finally caught up with him.

The next morning was a little awkward, but Andy didn't say anything. He just gave me a cocky smile, so I didn't know what to think. Since it was Saturday, I was more excited because I was going to meet Jeff tonight. I had other things to worry about like what I was going to wear and how I was going to do my makeup.

Over the next few weeks things were pretty normal between Andy and myself, until another Friday night when he came stumbling home drunk. We basically had a repeat performance of the first time, except he didn't force my head down as much. He still called me all sorts of names, but I must admit he certainly seemed to enjoy it. I guess the name calling was his way of feeling macho. He also came in buckets like the first time and I still wasn't prepared for it. I am not sure if you really can prepare for something like that!

For the remainder of my freshman year, I was probably "forced" to blow Andy maybe six more times. I guess Andy turned to his trusted roommate when he was drunk enough and just had to bust a nut. A couple of times he asked me to put on some of my girly clothes. I really did come to enjoy servicing that large cock and all that cum. Looking back, I realize those early experiences really play a large part in my sexual likes and dislikes today.







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.



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. 

*

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.

*

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.



Connie Goes to College Ch. 05



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. 





We had just arrived at the motel in preparation for our big date that evening. We barely got in the door when Jeff made mad passionate love to me, but for the first time did not use a condom. This took me by complete surprise and angered me at first, but I eventually calmed down and forgave him. Jeff went out to get us some beer, so I started getting ready for my first time 'out' in public. I had plenty of time before dinner, but I wanted to take my time and get everything right.  

I got out of my clothes and removed my makeup and I started feeling nervous about the big night. A warm bubble bath always relaxed me and made me feel sexy, so I filled the tub with warm water and stretched out under the bubbles. I almost drifted off to sleep when Jeff returned to the room with the beer. He handed me a nice cold one and excused himself to watch a little television so I could finish getting ready.

After I finished the beer, I shaved my legs again. I wanted them to be extra smooth for that evening. Then I filled my enema bag and cleaned myself real well again. After shaving my face and putting a light coat of bath oil all over my body, it was time to put on my makeup. I put on my silky robe and went into the bedroom area to get my makeup bag. Jeff was lying on the bed enjoying his beer and watching some sports program, so I leaned over and gave him a little kiss. I laid my dress over the chair and went back to the bathroom.

I started with a little concealer under my eyes and on the beard area. Then I applied a nice creamy foundation and finished off with some loose powder. To this day, my foundation routine remains pretty much the same. Then I applied some light gray shadow all over my eye area and some white shadow under my brow. I finished it off with some dark gray shadow in the crease, giving my eyes a smoky, sexy look. This was a technique Lynn taught me that I thought worked very well. I then lined each eye with a dark black liner. A couple coats of black mascara were next, giving my eyes a dark sultry look. It took me a long time to get used to applying mascara without poking myself in the eye, but lots a practice was the key. Having finished my eyes, I applied some blush to my cheeks in a dark pink shade, but not too heavy. I then lined my lips and finished them with a deep red lipstick.

When I compare my makeup choices between then and now, I realize not too much has changed. I still use many of the brands you get at a drug store, but I definitely supplement my collection with the more expensive designer brands. I know I have improved my techniques quite a bit too, but it is part of the ritual I truly enjoy. It is fun to start with a blank canvas, if you will, and paint on a feminine face. On the other hand, the part I hate most is removing my makeup.  

Next I sprayed my Oscar de la Renta perfume in all the key places. I know it might not be popular today, but back then I loved this scent because one of the prettiest girls in my high school wore it. Wearing it made me feel pretty and sexy!

I put on my black bra and matching thong panties, tucking my little penis as best I could. I took my brand new pair of off-black pantyhose out of the package and rolled them up my freshly shaven legs. This is another one of those things that feels so sexy and excites me every time. I absolutely love the feeling of nylons on my legs and wear pantyhose or stockings all the time. I carefully filled up my water balloon breasts in the sink, making them a little larger than usual, possibly closer to a C or D cup. I did take a precaution of double 'ballooning' just to be safe. I was fortunate not to have any of them bust (no pun intended) in the years I used them. Today I lean more towards the silicone falsies and hopefully soon I will have my very own, but I digress. I stuffed the water balloons in my bra and put on my black slip. 

I went back out into the bedroom area and put on my new black sweater dress. Jeff helped me zip it up and gave me a playful spank on the butt. I put on all my jewelry and went back to the bathroom to put on my wig. I chose a brunette shade in a shoulder length style for the evening. I carefully combed it out and placed it on my head. I styled it a little with my fingers to achieve the look I was after. I was pretty happy with how everything was coming together and was starting to think I just might be able to pull it off. I loved the way the dress fit and showed off my curves.

The last thing I had to do was put on my false nails. I had used the 'press on' nails quite a few times, but tonight I decided to attach them using nail glue. I tried this in the past, so I knew they would stay on better, but they would be much harder to remove. After I had attached the nails and filed them to get the correct shape, I coated them with a sexy shade of red.

As I waited for my nails to dry, I downed a couple more beers to calm my nerves. Jeff was about ready, so I put everything I needed in my purse and slipped on my new boots. I paraded in front of the mirror and loved the way they looked. They were actually fairly comfortable too.

Soon we were out the door and off to dinner. When we got to the car, Jeff opened my door and I slid into the passenger seat as my dress rode up my thigh. As we drove to the restaurant, I put my hand on Jeff's thigh, playfully rubbing and squeezing him. After a few minutes I 'accidentally' brushed up against his crotch and felt his hard-on trying to escape. I loved to tease him like this and the feel of his hard-on always made me feel sexy and wanted.

We arrived at the restaurant after a short drive and stopped in front of the valet stand. I was not very sophisticated back then (not that I am now) and had never used valet parking. So I had a slight panic attack when the valet opened my door and said, "Good evening ma'am!" Well, at least he called me ma'am. I did my best to get out of the car gracefully. Jeff came around to my side and I quickly grabbed his arm. It was now or never, so we proceeded inside of the restaurant. 

Jeff promised a romantic Italian dinner at a nice restaurant and so far I was really impressed. It looked absolutely beautiful as we went inside, but most of all it was dimly lit. We were seated at a nice quiet, candle lit table off to the side. Since it was fairly early in the evening it was not very crowded. I think Jeff had planned it this way.

Jeff ordered some wine and our waiter left us with the menus. I quietly told Jeff what I wanted so that he could order it for me. As I sat there my nerves started to get the best of me. It felt like everyone in the restaurant was staring at me. When the wine finally arrived I downed my first glass pretty quickly. The effects of the beer were wearing off, so I needed some more alcohol to calm me down.

Jeff ordered a veal dish for me and some pasta for himself. I didn't eat very much because I was so excited, but I remember the food tasted absolutely delicious. I tried to eat slowly, which wasn't too hard because I was still getting used to my long nails. We drank the bottle of wine fairly quickly and the waiter offered to bring another bottle. I indicated to Jeff that I had enough, so the waiter excused himself as we finished our meal.

Jeff looked so handsome in the candle light and he told me how beautiful I looked several times. He occasionally reached out and held my hand looking deep into my eyes. I would flirt back with him by rubbing my boot against the inside of his calf. The whole experience was very surreal to me and making me very horny. 

At one point during dinner, I felt the call of nature and excused myself to use the ladies room. I walked to the back of the restaurant, hoping there wouldn't be many women in the restroom. One of the two stalls was taken, so I quickly slipped inside the open one. I raised my dress slightly so I could pull down my pantyhose. I was tempted to pee standing up, but decided to act like a proper lady, so I sat down and went about my business. As I sat there I was hoping the woman next to me would soon leave. It seemed like forever, but eventually she left her stall, washed her hands and left. 

Now it was time for me to make my getaway. I quickly pulled up my thong and hose and straightened my dress. I opened the stall door and caught a glimpse of myself in the mirror. "Not too bad looking," I thought, but decided my makeup needed a little touchup. I dabbed a little powder on my face and as I was putting the final touches on my lipstick, the door opened and an older woman walked in. She greeted me with a quick hello and stepped into a stall. I don't know if she 'read' me, so I fixed my hair a little, put everything back in my purse and quickly got back to the table. I told Jeff about my bathroom experience, and he assured me that I looked great and that the woman probably didn't notice anything out of the ordinary. 

We finished our dinner and decided to pass on dessert. Jeff paid the waiter and we went outside to get the car. As we were waiting for the valet to bring the car around, Jeff put his arm around me. I responded by turning to him and giving him a big kiss.

"Thanks for dinner! It was wonderful," I said as I hugged him.

"You're quite welcome. I am glad you enjoyed it. Are you ready for the movie?"

"I can't wait!" I replied as the valet got out of the car and opened my door.

We drove to the movie complex and bought our tickets. Jeff and I held hands as we walked towards our movie. We entered the dark theater and let our eyes adjust as we looked for a place to sit. We decided to sit near the rear of the theater and settled into our seats. I enjoyed sitting there in my new dress and boots as Jeff placed his hand on my knee and rubbed my nylon covered thighs. To this day, I still melt when my date caresses my leg in public.

My nerves had really calmed down at this point. Between the dark theater and Jeff making me really horny, I was really enjoying my time dressed in public. As the movie ended, we sat there waiting for most of the crowd to leave. Jeff leaned over and we kissed for a few minutes before heading to the car. On the ride back to the motel, I rubbed Jeff's thigh and nibbled on his ear as he tried to concentrate on driving. Arriving at the motel, we practically ran to our room.

As we entered the room, Jeff tackled me onto the bed and we began kissing very passionately. Our tongues explored the inside of each other's mouth and I began moaning like a school girl. Jeff was on top of me and I could feel his hard cock against my thigh as he slowly started humping me. My own cock was straining to get out of my panties and I could feel myself getting wet. Then I remembered that I brought some lingerie especially for this night.

"Hey baby, why don't you give me a minute to change into something more comfortable?" I whispered into Jeff's ear.

"Sure Connie, but you better make it quick. I don't know how much longer I can take it!"

I quickly got up from the bed and dug a few things out of my suitcase. I went into the bathroom and removed my boots and dress. I also removed my pantyhose in favor of some jet black thigh highs. Next, I put on a black teddy and matching short robe. I slipped into a pair of high heeled fuzzy slippers and checked my makeup. I added some more lipstick and walked back to the bed with the sexiest walk I had.

Jeff was already laying on the bed naked, his beautiful 7-inch cock sticking straight up and oozing some pre-cum. "Wow baby! You look great. You know that is my favorite outfit."

"Yes I do! I brought it just for you. Now it's time to thank you for dinner and the movie!" I said in a low sexy voice. I got on to the bed and crawled on my knees between Jeff's legs. I lowered my head to his crotch and licked the pre-cum from his cock. Then I put just the end of his dick in my mouth and let my tongue to swirl around the head, causing Jeff to let out a moan. I knew he wouldn't last long, so I wanted to tease him as much as I could.

I continued my tongue assault on his cock and I could taste his cum leaking from the tip. I slowly worked my lips up and down the shaft, pausing when I got down as far as I could. I sucked slightly as I raised my head, stopping as his cock rested on my lips. I took Jeff's cock in my hand and admired how red and hot it was and could feel the blood pulsing through the veins on the underside. Then I continued bobbing up and down on Jeff's cock, giving his entire cock a tongue bath. I felt his balls begin to pulse and soon I was rewarded with a mouthful of his love juice. I savored the salty and slightly bitter taste as I swallowed all of it. 

"Yummy, I love the taste of your cum, baby!" I said as I licked my lips.

Jeff was practically speechless as he lay on the bed trying to catch his breath. "Oh my god, Connie! That was great, but I am not done with you yet. Give me a couple of minutes so I can return the favor!"

I crawled next to Jeff and he put his arm around me. As we cuddled, we talked about dinner and the movie and what a wonderful time we both had. Jeff and I started kissing and within a few minutes I sensed Jeff was getting horny again. I glanced down at his crotch, and sure enough, he was rock hard and ready to go. 

Jeff rolled over on top of me and pulled my panties down. He took my penis into his mouth and hungrily sucked on it for a few minutes before I had to stop him. Jeff was always very good about taking care of my needs, but I liked to hold back from cumming until my lover was completely satisfied. I am still this way today, and I think it is mostly due to the fact that I tend to lose interest in sex after I cum. 

"Oh honey, that feels so good, but I need you to make love to me. I have been thinking about it all night and I need to feel you inside me. I want to make love all night long!" I begged. I had really come to enjoy, or maybe need to have Jeff inside of me.

"Connie, be careful what you wish for! I could screw that ass all night long and you will be begging me to stop."

"I have an idea. Let's do it in front of the window!" I suggested.

We turned out all the lights in the room and opened the curtains. I positioned myself bent over in front of the window with my hands on the air conditioning unit.

"Should I use a condom?" asked Jeff.

"No, that's ok. I want to feel you cum inside me again. I was mad at first, but I think it is kind of sexy."

Jeff came over to the window and I felt that familiar cold feeling as he spread some KY jelly between my ass cheeks. As I looked out the window over the parking lot, he lined up his cock and started pressing against my hole. I just love the feeling as the head of his cock starts to enter me. Jeff paused for a moment, and then continued to slide all the way in.  He continued fucking me for several minutes as we got into a rhythm, and I was in heaven. I think I saw some people in the parking lot look up at our window, but at this point I didn't really care. 

Eventually, Jeff was getting tired and my arms started to hurt, so we went back to the bed. I got on my back and Jeff got between my legs. I put my heels over his shoulders and he entered me again. We stayed in the position for awhile and then switched back to doggy style. I don't know which position I prefer, I just know I loved every minute of it. I couldn't believe Jeff's staying power, but since he already cum I knew it was going to be awhile.

I was starting to get a little sore, and I wanted to cum pretty badly at this point, so I started encouraging Jeff. "Oh baby, that feels so good. I want you to come inside me so bad, Jeff! Your hard cock feels so good!"

Jeff continued to pound away and acknowledge me with a grunt or two. I started to stroke myself when Jeff said he was getting close. He picked up the pace and I started to stroke faster. Within a few minutes he slowed down and was taking long and deliberate strokes. He let out a guttural moan and I felt my insides getting flushed with his cum again. It was such a warm feeling deep inside me and sent me over the edge. I started to cum all over the sheets below me as my whole body trembled. After several strokes, I collapsed and Jeff fell on top of me.

When we both caught our breath, we rolled over on our backs. My lingerie was covered in cum, but I was too tired to get up and clean myself off. We both dosed off for awhile after having a wonderful passionate night together. We woke up early in the morning and made love one more time before changing and getting on the road.

That first public date will always be very special to me. And while I still enjoy going out on dates, the first time will always be special. I don't think I could have asked for a more perfect time.  





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.



Connie Goes to College Ch. 06



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. 

*

My freshman year in college became quite a year for me in terms of defining my femme side, while also providing quite a contrast. On one hand, I had a wonderful romantic relationship with Jeff in which we 'made love' together. On the other hand, there was my roommate Andy who thought he was 'forcing' me to give him head. I was Jeff's girlfriend, but I was Andy's sissy roommate. Jeff usually took care of my needs if I let him, whereas Andy just considered me his cum dump. Jeff was definitely more caring and enjoyed having a girlfriend on the weekends, but Andy just needed someone to relieve his frustration.

It was a typical Friday night and I was in my dorm room studying when the phone rang. It was Andy and he sounded pretty drunk. There was a lot of background noise and it sounded like he was at a party. "Hey sissy! I'm glad you are still home. I want you to do me a favor."

"Uh, ok. What do you need, Andy?" I replied, almost afraid to ask.

"I want you to put on some of your 'special' clothes tonight. I have a feeling I will need your help later," Andy said with a wicked laugh. "Try to make yourself real pretty. Some lipstick would be nice!"

"Andy, I am not so sure about this. I am really trying to study."

"Listen here, faggot! Don't disappoint me. Or would you rather I tell everyone on the whole floor about your girly side?"

I knew Andy wouldn't tell anyone, but I didn't need the hassle either. "Fine, just be cool, ok?" I said as I pretended to be worried.

"Ok, I will there in an hour, sissy!" Andy said as he hung up the phone.

Fortunately, I kept some spare clothes in my closet along with some older makeup. I ran down to the common bathroom and quickly took a shower and shaved my face. When I got back to my room, I applied a light coat of foundation, a little mascara, eye shadow, blush and lipstick. I had an older wig that I didn't really care for, but it would have to do the trick. Then I put on some panties, pantyhose and a night gown. It wasn't my best work, but it was good enough for Andy.

I sat at my desk trying to study for awhile until Andy arrived. I heard him try to open the locked door, so I got up to let him in. As I opened the door, Andy stumbled inside but he also had a friend with him. I recognized him from Andy's lacrosse team. "That bastard!" I thought to myself. "How could he do this to me?"

"Hey sissy! I see you put a little extra effort into getting pretty tonight," said Andy in a degrading tone. "I want you to meet my friend Peter. I told him all about you and he said he would love to meet you!"

Peter was built similar to Andy, but maybe an inch taller with darker hair. I had seen him around campus hanging around with Andy a few times, but I never really talked to him before. They closed the door behind them as I stood there totally embarrassed. My first instinct was to run out of the room, but that wouldn't have been such a good idea.

"Wow Andy! I thought you were kidding. Your roommate does make a cute girl," exclaimed Peter.

"And best of all, he, or she, has a hot little mouth!" replied Andy. "He needs a little convincing, but he will suck your cock. Isn't that right, sissy?"

I just stood there and shook my head. "No way, Andy! I am not going to do that. I just put on this stuff to play a joke on you tonight." I was desperately trying to find a way out of this.

"Bullshit, you little faggot! You know you like it. I just want you to take care of me and my buddy here. Nobody will know, I promise." Andy was doing his best to convince me as Peter was standing there checking me out.

"Look at that Andy," said Peter, pointing to the front of my pantyhose. "I think she is actually getting excited."

Sure enough, I had a raging hard-on that was pretty obvious, given the lack of clothes I was wearing. I figured I might as well get it over with and stop pretending it didn't excite me. "Ok, I will do what you want. Just promise me that you won't tell anyone else."

"I knew you would see it my way. And don't worry, I won't tell anyone else. Peter here is pretty cool, but I don't think the other guys on the team would understand. "

"Your secret is safe with me," Peter assured me.

Both guys quickly removed their shoes and pants and stood before me in their underwear, which was outlining their hard dicks. I got on my knees in front of them and started massaging their cocks, one in each hand. I could feel both of them getting harder and straining to get out of their cotton confines. I pulled their underwear down to their ankles in one swift motion as their cocks sprang to attention. Both Andy and Peter had gorgeous cocks. They were similar in length, but Peter's was slightly thinner and had a bit of an upward curve.

I stroked each cock slowly as both guys let out a moan. There was pre-cum starting to form on each so I licked it off, first Andy and then Peter. I decided to start with Peter, so I wrapped my lips around his cock and started slowly taking him into my mouth. As I was doing this, I continued to stoke Andy to keep him nice and hard. 

I was barely getting into a rhythm with Peter, when I felt him tense up and cum in my mouth. He wasn't a heavy cummer like Andy, but it surprised me how fast he came. I tried to keep sucking him to get all the cum I could, but he quickly pulled his cock from my mouth. I had a feeling he was one of those guys whose dick got really sensitive after cumming.

"Oh my God, Andy! You were right. Your roommate does give good head," Peter said, as he tried to catch his breath. "I can't believe I came so fast!"

"Alright sissy, it's my turn," said Andy as he relaxed on the bed. "Get that mouth over here and start sucking!"

I crawled to the bed and got between Andy's legs. I could still taste Peter's cum as I began sucking on Andy's big cock. Sometimes it would take Andy awhile to cum, especially if he was drinking. When he first made me blow him, I just wanted to get it over with because of the humiliation. But after a few times with Andy, I learned to enjoy the role of cock sucking little sissy. I took pleasure knowing I gave him a better blowjob than any girl he dated.

As usual, Andy started calling me names as I sucked him. It didn't take long before Peter joined in and started calling me names too. While I was embarrassed having someone watch me suck my roommate, it also starting turning me on. I didn't realize it, but I was moaning and rubbing myself against the comforter. Apparently, this started to turn-on Peter too and I felt a hand starting to rub my ass.

"Your roommate has a pretty cute little ass, Andy. Have you ever fucked it?" asked Peter.

"No way, dude. I only let the sissy give me head when I need it. I am not into that shit!"

"Do you have a condom? Watching this sissy suck your dick is making me horny again!" said Peter as he started stroking himself.

I couldn't believe what I was hearing as I continued sucking on Andy. He told Peter where to find some condoms and a few minutes later I felt him get behind me. Peter roughly tore a hole in the back of my pantyhose and practically ripped my panties off of me. I was a little surprised by his aggression, but I did little to stop him.

Then I felt his cock start pressing in between my butt cheeks. He wasn't going to waste any time and tried to enter me in one stroke. Unfortunately, there wasn't enough lubrication and he didn't get very far. He tried a few times and it was starting to hurt.

"Hey, take it easy back there. You're hurting me," I pleaded as I took my mouth off Andy's cock.

"Sorry about that. I am not trying to hurt you, but I bet you are one tight little bitch!" said Peter. "Do either of you have any lubrication?"

Neither of us had anything to offer and Andy told Peter he was out of luck. Andy then grabbed my head and shoved it down on his dick again. I could hear Peter rummaging around our closets trying to find something. "I think I found something," offered Peter.

Peter came back to the bed and I felt something press against my asshole. Then there was this feeling of a cold liquid being injected inside me as he was getting himself into position. It didn't take long before he was able to get his entire dick inside me. He paused for a moment and let out a sigh of relief.

"Nothing like a little conditioner to ease the way!" exclaimed Peter.

"That is too funny, dude. I can't believe you did that!" said Andy as he started to laugh.

I couldn't believe Peter used conditioner either. It felt like he used half the bottle as he started to thrust in and out of my ass. It felt very strange and the whole experience was pretty gross, but at least it didn't hurt. I won't go into any more details, but let's just say I didn't have much choice but to try and please them both and hopefully get to bed.

I continued to suck Andy as Peter had his way with my ass. Both guys seemed to be having a pretty good time. Andy was hard as a rock and leaking pre-cum and Peter was assaulting my rear with long strokes, occasionally pushing me forward. Sometimes it was difficult to keep Andy's cock in my mouth, but I did the best I could. 

After a few minutes, I wrapped my hand around the base of Andy's dick and then started to massage his balls. He let out a moan and said he was getting close. I couldn't wait for my reward and knew I would soon have a mouthful of salty cum. As Peter picked up his pace, I felt Andy's balls tighten and unload a blast of cum, hitting the back of my throat. I kept my lips wrapped around the base of the head as he continued filling my mouth. 

As Andy collapsed on the bed, I turned my attention to Peter and began moving my hips and clenching my sphincter. This had quite an effect on him as he let out a low guttural moan. I continued to tease him by clamping down on his cock, and I got a response out of him every time. He was starting to work up a sweat and I had a feeling he was getting close as Andy just watched the show. Sure enough, he slowed down a little and finished screwing me with a few deliberate pumps. He sounded so cute when he finally came and I imagined him filling up the condom deep in my rear. 

Peter finally pulled out and collapsed on my bed. Both Andy and Peter gave each other a little smile before kicking back and relaxing. I couldn't wait to get out of my clothes and get to bed. Peter finally got dressed and left, but not before thanking me for a good time. I wasn't expecting a kiss, but I guess it was nice he thanked me. Andy passed out pretty quickly like he usually did, so I cleaned up and hopped into bed myself. Soon I was drifting off to sleep, thinking about what had just happened. It wasn't something I would have ever imagined, but I was glad I got to experience it.