Cheerleaders and Linebackers

Story Info
Caught in girlfriends clothes a CD has to show off at party.
16.2k words
4.69
30.9k
47
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

(This is a story I wrote a while ago I hope you like it.)

***

"We're leaving. Are you sure you don't wanna come?" Lydia, my girlfriend of a year and a half laughed.

"No, I'm just going to relax and try on a couple of different outfits I got from Amazon," I said.

"Are you sure?" She pushed, "The guys would love to see some legs at this party, I'm sure you will be wearing something short."

"Something short and slutty, ha." Her friend Ava cut in. "Well if you change your mind I'm sure we could get one of the guys to pick up your ass, haha."

Lydia asked "Just one?" "I'm sure we can get them all to make the trip. Ha," The door shut on their laughs. I was glad they were gone.

Sunday night's Lydia and Ava would hang with their friends to watch Sunday football, their Cheerleaders and Linebackers party. It's a tradition that has been going on longer than I have known either of them. Every September it starts and the whole day is shot getting prepared for it. I hate football, and I never wanted to go. Last year I did relent and go once, they said it was a big game, big bore, I couldn't wait to leave. It's held at their friend Ross's apartment. He has a lot of space and he always caters it. They had 3 TV's going at once and there were at least fifteen people there. Lydia originally said she wanted company but she spent all the time with Ava, making fun of all the women, and complaining about the food. The two of them barely paid any attention to me and they barely even watched the game. I really don't know why they even go or took me. I prefer staying at my apartment and doll myself up.

I'm a crossdresser and nothing made me happier than Lydia and Ava leaving for their party. I couldn't wait for this September to come. The rest of the season I would have Dress-Up Sundays.

***

I met Ava when she screamed 'FUCK!' at the top of her lungs during a bar fight at a sports bar that I co-owned, called 'The Left Field'. I didn't go there too often but when I did I always ran into her. I use to have the bartenders buy her drinks, 'cause she was always with a crowd and I wanted to stay on her good side. She accidentally introduced me one night to Lydia, her colleague at a Law Firm. We started dating right away, even though I wasn't looking for anyone. I had just moved into my current apartment and was relishing my time alone to dress up. Also, I could tell Ava wasn't too thrilled with me going out with her best friend.

Both Ava and Lydia are short, 5'1" with short dark hair. They could be sisters. Both of them are well put together and they always made an impression on the people they met. They have hung out with that same group of friends since they graduated eight years ago from high school, and all their friends call them 'The Tinkle Sisters' because they were always in the bathroom together. This happened a lot and I never asked.

Lydia learned about my crossdressing on our fourth date. I didn't want any surprises, like my last girlfriend, especially since I had such a big wardrobe. She was very confused at first and I didn't hear from her for over a week. It turns out Lydia was bi and she literally just broke up with her last girlfriend and really didn't want another one. She asked questions about my sexuality, and when I told her I wasn't gay just your average CD she seemed a little more appeased by the situation. I think she wanted a boyfriend who was a little more masculine and stable than she was used to, if I was anything I was stable.

Once she got over the initial shock and talked it over with Ava, it all just became another thing to her. She called it my little hobby, and she loved to tease me about it. She would ask the day before one of the football games, "Are you working on your little hobby tomorrow? I wish you would work on the sink."

When she said things like that I always thought 'I could do that but I don't want to break a nail. Or get my pretty dress smudged.'

Neither of them at that point in time, ever saw me dolled up as 'Sabrina' completely. Lydia made me show her and Ava when we first moved into the apartment together, but I didn't do my makeup or hair, I was a little embarrassed. I didn't want them to see how good I was at it. She shook her head and said, "If you are going to do this, do it right. At least shave your legs a little better and get a wig. It's one thing dating a crossdresser, it's another thing dating an ugly one."

And on that note, my dressing went up about 12 notches. I went out and had a Brazilian wax from a crossdresser-friendly place I found on the net. My body was completely free of hair now, smooth and soft. They even started me on hair removal, working their way down. I also went on a diet and even started exercising more, I wanted to focus on my female form. Looking in the mirror was a big difference compared to last season. I went from a size 20 down to a size 10-12. Lydia didn't seem to mind as long as I didn't look feminine in guy mode. I always had to make sure my mascara and nail polish was completely cleaned off before she saw me. I also couldn't leave my female clothes lying around, Lydia didn't want to be reminded about the other woman in the apartment. I kept everything hidden in the back closet.

Ava started taking a very noticeable dislike to me once Lydia told her of my crossdressing. One day she saw some of the dresses I got back from the dry cleaner. "I bet you dress just like Celeste." Celeste was dating their friend Ross for about three months when she moved in with him. Both Ava and Lydia didn't like the new girl too much, they always said she was after his money and status. "Always showing off her long legs and big boobs. You would think she was an understudy at a fucking strip club."

I tried not to pay attention, so I put my dresses away and hoped she would forget about me. Ava said, "Ross always dated those types of girls, even in school, dropping them once he got tired of them talking about their fucking clothes."

Lydia just laughed. "You know, Sabrina does have the right bra size to date him."

Ava looked at me. "And IQ I bet, haha."

***

Last football season, When Lydia first let me stay home on Sunday nights to dress up, she gave me two rules. "One; you can't wear my clothes. You have plenty of your own. I don't want to be wearing something to work and find stains, or it's stretched out in all the wrong places. And two; since you are so 'nervous' about being seen, no going outside. Stay home, take pictures, talk on the computer, I don't care. I just don't want the neighbors asking me who the cute blonde is they keep seeing sneaking out of the apartment on Sundays. That's ALL I need."

I shook my head, "What about never feed me after midnight?" She didn't laugh, but I agreed, mainly because I never leave the house anyway as a girl, and if I did it's only to go driving around late at night. Plus her clothes are just way too tame for me. Lydia's whole life revolved around plain and simple, which explained her eating habits as well as her style. When we first met her clothes would never even fit me, but now after dieting and more exercise I'm sure I would be able to slip into them, they would just be too short.

"Okay," I told her. "I will stay home and be good."

She laughed. "Yeah be good," she said sarcastically.

***

The football season started so wonderfully. Since I reached my goal of 155 pounds, I had to get a new wardrobe and everything fit perfectly. I gave all my larger sizes to Goodwill and replaced them with smaller, sexier dresses and skirts. I threw out my old wigs, and the three Lydia helped me pick out were also fabulous and I never looked more like a woman than I did now. I bought C cup breast forms and started taking my makeup much more seriously. For the next couple of weeks from September through November, everything was coming together like never before. I loved the woman that was emerging in my mirror. I have been crossdressing since I was a child but now I was coming into my own. I needed Lydia to push me in the right direction and become even better at it than before, though I would never tell her that. When Lydia would get home around 11:30 after the game, I would make believe I was sleeping, in our small back bedroom, so I could sleep in my stockings and nightgown. I was never prepared to stop being a girl. The end of the night always came way too soon.

***

The week before Thanksgiving that year I decided that with my look I could easily pass as a real female, and decided to go out. I had been out before but it was years ago before I even knew Lydia. I used to drive to the mall, walk to the door and then walk back to my car, I have done that a lot. But now things seemed so different. I felt like a lot of femininity was rubbing off on me due to the proximity of living with a woman. I had been working on my voice and it was definitely more feminine than before. I wanted to buy some makeup at the pharmacy and maybe pick up a couple of bottles of wine. I just needed an outfit to blend in with the other women in the stores. Looking through my wardrobe all I could find, of course, was low-cut sexy dresses, miniskirts, and gowns. Nothing appropriate for a night of shopping. Plus all my colors were so bright and would stand out way too much. I would have to make some major purchases so I could do this properly in the future.

I decided, against my better judgment, to look through Lydia's closet. I would find something to help me blend in. Lydia's favorite color was black and most of her wardrobe blended into the background. My eyes went immediately to one of her only dresses. It was dark purple and full of black flowers, this was the dress she wore when she had to get a little dressed up. It was a little loose and long on Lydia, but on me it was perfect. It clung to my boobs and the bottom was full giving me the illusion of bigger hips. The hem came below my knees showing just a little bit of my calves. After slipping on nude pantyhose and my two-inch heels, I worked on my makeup. I went on the subtle side, I was just a woman running a few errands on a Sunday night. I definitely didn't want to be noticed.

I had to put on one of Lydia's black coats too, since I didn't have one of my own, and I took my pocketbook and slowly made my way down the two flights of stairs. My heart was beating so loud, I had never been so nervous before. I decided to put on my sunglasses, for some reason it made me a little more comfortable, plus I didn't have to make eye contact with anyone. There was only a couple of people in the lobby, and outside the building, it was deserted. I'm sure everyone was watching the game since The Rams were playing. I took a deep breath and got in the car to drive a couple of blocks to CVS. It was an easy walk but there was no way I would be able to make it outside of the car, clicking in my heels.

I loved walking around the store, it's so much easier shopping and looking for little things instead of getting them online. The store was empty for 8:30 on a Sunday night and I walked up and down the aisles like I only dreamed about. I picked out a new deodorant and shampoo and even found a couple of pairs of pantyhose. When I made my way to the makeup counter a young girl helped me pick out some new mascara and smudge-proof lipstick. I couldn't tell if she read me, but she was very nice and so helpful, I didn't really worry about it. I thanked her and headed to the cashier feeling like I completely passed.

Going to the liquor store was even easier. I was feeling ready to celebrate so I found some Chambord liqueur and Champagne to go with the two bottles of wine I had. A young man even helped me with my items, when he called me Miss I felt so good. Even the cashier told me. "Have a goodnight, Ma'am, here's your change." Mmm, I was suddenly so excited, I was glad my dress was so full and I was tucked in nice and tight. Once back in the car I parked someplace dark and rubbed myself until I came. I continued to relax as my panties dried and the windows fogged. I was so hard by this little jaunt, there was no way I would have made it back to the apartment, this excited.

When I got back to the building I didn't even care that there was a couple of more people in the lobby than before, I put my dark glasses back on, but I tried to at least smile. I was hoping that they were looking at my legs, the little that was shown. I clicked and clinked up the stairs with my purchases in hand. I stood in front of our door looking for my keys in my pocketbook just totally enjoying this whole new experience. What a great and successful idea, I was thinking. I slipped the key in and opened the door.

"So I thought you were too afraid to go out?" There stood Lydia and Ava waiting for me, both with their arms folded over their breasts. Lydia suddenly got madder. "And you got to be kidding me. Is that MY coat AND dress?" Oh, shit I knew I was in trouble, caught red-handed.

Ava laughed. "I knew you would look just like Celeste, you even have the same hairdo."

"Sorry. I'm going to go and change." I begged.

"Don't you dare," Lydia yelled. Put that stuff away and then get in here." God, I have never been so nervous. When I was a kid I used to lock myself into the basement bathroom to dress up. Nobody ever bothered me and I never got caught. Now getting caught by these two women was making my manhood shrink to nothing and making my throat completely dry. I was shaking as I sat on the chair across from the two women on the couch, crossing my legs at the ankle. "This is unacceptable," Lydia said. "I can't believe you, we had two rules, and you broke both of them. And there are people downstairs. What were you thinking?"

Ava was studying me. "Lydia look at those legs, and those nails." She got up and grabbed my hand, "these are better than mine. I can't believe you get them to look this good." I cleared my throat. Ava sat back down and looked at Lydia. "You know what we could do? Let's have Sabrina here be our own personal nail technician. Just think of the money we'd save, ha."

Lydia reluctantly agreed and said. "She needs more of a lesson than that." She looked towards the ceiling in deep thought. "You know what, since you look so stunning as your female persona, from now on YOU are coming with us to the Sunday night football parties, or more specifically, SABRINA is coming with us. And don't even try to get out of it."

***

The next weekend as Sabrina started early. That morning I went out and had the last of my hair removal on my face, dressed as Sabrina for the first time. The salon women there were very surprised and proud of me. I then bought a mixed set of false nail tips and art acrylic manicure gel, along with a UV LED nail lamp and over a dozen colors. When I would attempt something Lydia would get mad if I didn't go all the way and do it right. The girls then took me out shopping to get me more prepared to be seen by others. Once home I had to make lunch and then dinner, before getting ready that night to do their nails. And of course, they wanted me to wear something sexy and revealing, so they could tease me.

I was a nervous wreck thinking that I would have to pass at this party, though only a couple of them knew me as Lydia's boyfriend. I was on edge the entire Saturday, but first I had to decide on an outfit. I put on a short white mini dress with a ballerina neckline, it had lace on the short sleeves and the hem, and it was very feminine. I knew if I didn't dress up nice the girls would make me change over and over again, and I didn't want them getting mad at me. They could be so mean. I was also going to try and convince them one more time to let me stay home still on Sundays, specifically tomorrow night. I didn't want to meet her friends in a dress, especially since I knew the girls wouldn't be keeping me company. They would move on into a corner and leave me to fend for myself.

I put on nude sheer pantyhose and 5-inch white sandals which strapped around my ankles. My hair went up into a ponytail and I left some wisps over my ears. I looked very feminine especially with my dark false lashes, smoky eye shadow, and my new plum lips.

"Oh my God, you are so beautiful. Turn around let me see that hair." Lydia gushed and shook her head when I walked in on her and Ava. "What's crazy is you are SO not my type, you are SO girly. Ha. I bet you have more lace on your lingerie than I have in my whole wardrobe"

"That makes two of us." Said Ava. "Now let's get to work girlfriend. Time to work off your punishment." They were amazed at how good my mannerisms were and how soft my voice was. I was still uncomfortable being dressed with them but Lydia did make me a little more relaxed with her backhanded compliments.

Ava just kept on commenting on my breast size. "The guys are never going to look in your eyes with those puppies in front of them tomorrow." They laughed and said it would be good for me to meet new people after I had my little public outing the week before.

I tried one more time. "Can't I stay home, please? I will do all the laundry forever, while you two have fun."

"No way," Lydia said, "You knew the rules, you reap what you sow. I just hope it's not as cold as last week, they had absolutely no heat, that's why we left so early. Ross said it's all fixed now."

Ava added. "Celeste was running around with a comforter around herself all night, she is such a fucking drama queen. I think she was just hiding her hard nipples."

The only nice thing was, I did get to spend the entire weekend as Sabrina. Now, I was still nervous but I didn't mind going out tomorrow night all dressed up and being surrounded by people admiring my look. I just had to make sure I kept my voice as feminine as possible, that was my only real downfall.

Lydia told me I could dress as flamboyant as I wanted. "Celeste and Anabella always come to these things dressed like supermodels. I don't even think you will stand out as much as you think."

Finding a look was more difficult than I imagined. Lydia didn't want to be involved. It took most of Sunday afternoon to find something sexy but suitable. I finally selected a blue lace long-sleeved mini dress. I had on tan pantyhose and gold 5-inch pumps and a matching clutch. I wore my long strawberry blonde wig which came down to the middle of my back. I put on big gold hoop earrings and a couple of bracelets. A little spray of perfume and I was ready before Lydia, who was wearing tight black jeans, a top, and low-heeled boots.

When she saw me she said, "Wow, Look at those legs. I guess someone is not going to be hiding in the background. Maybe I should rethink your punishment and make you become a waitress at 'The Left Field' instead, ha. It might be fun to watch all those horny men ogle you all night." I just smiled and told her I was so nervous I haven't eaten since the day before. "Aww, well there is plenty to eat at Ross and Celeste's, I just hope the drinks don't hit you too quickly, you need to focus on not falling off those heels. Now let's go get Ava."

***

They lived in a huge apartment building in the middle of LA. We made our way to the 26th floor, with me tagging behind in my high heels, holding a bottle of Merlot and my clutch. Ava kept on telling me to hold my dress down in the wind. "C'mon bitch, don't show everyone your little package." She would laugh.

Ross and his girlfriend kissed us as we walked through the threshold. "And who is this lovely lady?" He asked.

"Ross, Celeste," Motioned Lydia. "This is our friend Sabrina, she's hoping she can become a fixture at our Sunday get-togethers."

"That would be fine. We can always use another cheerleader." He said looking at my boobs and then my legs. "The more the merrier. Come in I will get you a drink."

There were over a dozen people there, men and women, and I knew exactly who Anabella was. She and Celeste were beautiful and I loved their dresses, these were the type of women I wanted to become and now I understood why the girls didn't like them as much. Those two introduced me to everyone.