The wingman

Chapter 1

Dave and I were best friends and in the same fraternity at University. I could be counted on to double date, if Dave asked a girl out and she wanted to bring along her roommate. Most of the time the roommate was either a chubby or not very pretty, I was always a good sport and a polite and considerate date.

My name is Nat by the way. I’m overweight myself being five foot ten inches and tall and now at university close to two hundred pounds. I have a pot belly, bubble butt and thick thighs. Though I’m “heavy”, I’m still what most girls would call cute.

Dave is tall, slim, athletic and handsome. He loves the slim, tall, well “boobed” hot girls and he is never shy about asking them out. I on the other hand am quite shy, especially around girls. I do have one advantage; it is I love chubby and overweight girls.

Dave wanted to date a girl named Clara. She was very pretty, tall, slim, nice “chest”, great booty, long slim legs, a total hotty. She also was a very nice person, very sweet and considerate. Clara’s roommate, physically was her polar opposite. Lisa was morbidly obese, weighing two hundred and twenty pounds, standing five foot two inches tall. She was what I call,” all belly and booty”. She had a huge protruding belly, beach ball size bottom cheeks, and thick round thighs. She was despite being obese, very pretty, nice smile, pretty eyes and hair.

Clara and Lisa’s moms were friends. They were both delighted that their daughters would be attending the same university.

Lisa’s mom and Lisa, after looking over the dorm accommodations, decided given all the dorms had public style restrooms, that shy Lisa would need to live in an apartment. Her mom didn’t want her to be alone, and asked Clara’s mom if Clara would room with Lisa in the apartment. Lisa’s family was very wealthy and renting an apartment on top of tuition was not a problem at all. Clara’s family though well off, appreciated that Clara could live at university room and board free.

Clara and Lisa were good friends having attended high school together. Clara was Lisa’s quasi-defender, when mean boys would tease her, Clara would step in and admonish them. Since nearly every boy in the school wanted to date the super- hot Clara, they usually walked away chastised.

The apartment arrangement worked out well, both girls enjoyed the privacy of their own bathrooms and large bedrooms. Lisa’s parents had arranged maid service and even grocery delivery. The only issue for Lisa was getting to classes on time. Being so obese she walked very slowly do to her round thighs. She planned her class schedule to be sure she time to get between buildings and that the buildings had elevators. She didn’t appreciate the folding desk style chairs that nearly every lecture hall, class room had. They were not friendly to someone who has and forty eight inch waist. Despite these issues Lisa was very comfortable with her body and figure; both of her parents were morbidly obese as well.

Clara was always concerned about how Lisa was copping with university life. She was concerned that Lisa had never dated. Lisa was into fat guys, but most of them in high school were either super nerds that didn’t take good care of their hygiene or they were not into fat girls.

When Dave approached Clare about going out, she was delighted. She had a couple of classes with him and she could tell he was a nice guy the way he interacted with his classmates. Dave came up to Clara, “Clara, would join me for a cup of coffee?” Clare smiled, which usually lit up a room, “I’d love to Dave.” They walked to the student union building and got a table. Dave got coffees and sat down with Clara.

Dave and Clara chatted, where they were from, where they went to high school, what sports, activities they were into etc. Dave asked, “Clara, I would be delighted to take you out to dinner and see a show or movie.” Clara smiled, “I’d love to Dave, but I have one request or maybe a favor.” “What’s that?” asked Dave. “My roommate, is very obese, and never dates. She is really cute though and a very nice person, can you ask one of your friends to double date with Lisa and I?” Dave smiled, much to Clara’s relief, “Yes, one of my best friends, Nat, he’s a little heavy, but nice looking guy, he kind of likes heavier girls too, I’m sure he would love to join us.” “Oh, Dave that would be awesome, thank you so much.” Dave said, “Did Lisa take history second semester of freshman year?” Clara thought for a moment, “Yes she did, why?” “Nat said something to me a about a really cute fat girl in his history class, but he was too shy to ask her out.” Clara thought, “You know, Lisa mentioned that there was a guy in her history class that was checking her out, when she looked at him he smiled, but never said anything to her. Oh Dave this really could be a great evening for them both.”

When Dave got back to the frat house he asked me, “Hey Nat, do you want to double date with me?” I always trusted that Dave would never set me up with some shrew, so I agreed. “Sure Dave. Who are the ladies?” Dave replied, “ I got a date with Clara Smith, you know the super hotty in my poly si class and she wants to bring her roommate, Clara Mason, she’s really obese.” I thought, “Hey did Clara know if Lisa took history second semester of freshman year?” “I asked,” replied Dave. “She did!” “Oh Dave, I’m sure she’s the adorable little fatty I was pinning for in that class.” I replied.

We set the date up for Friday evening of that week. I couldn’t weight to meet the adorable, little fat girl I had seen in history last semester. The day arrived and Dave and I drove over to the girl’s apartment building. “Wow Dave, these girls are living pretty high, this is an awesome building.” “Clara told me that Lisa’s parents didn’t want her to be un-comfortable in the dorm, due to her weight, so they got this apartment. Clara and Lisa’s moms are really good friends so they offer Clara room and board to be Lisa’s roommate. Lisa and Clara were friends too, so it was a prefect deal for everyone.”

We got up to the girl’s apartment and rang the bell. Clara opened the door, I thought Dave might faint, she looked so hot. We were going out to dinner and then a play downtown. Clara was wearing the standard little black dress, white stockings, black pumps and a little patent leather clutch. Dave just gushed, “Oh Clara, you look amazing!” Clara blushed, “Thank you Dave that was very nice of you to say.” Clara said, “You must be Nat, thank you for joining us. Nat this is Lisa, Lisa, this is Nat.” We all chuckled at the introductions. I went up to Lisa, she was sitting wearing a very tight black dress also. ”Hi Lisa, it’s nice to meet you.” Lisa giggled, “Nat, weren’t you in my history class last semester?” I blushed, “Yes Lisa I was. I remember seeing you there too.” “Nat I saw you looking at me.” I blushed, “Yes I was checking you out, but I was too shy to ask such a hot girl out.” Lisa’s smile lit up the room. Clara nudged Dave, he looked at her and she mouthed the words “thank you” to him, he winked back. We got ready to go to dinner, Lisa asked, “Nat, could you help me up?” “Certainly!” I replied and took her hands and leaned back and got Lisa to her feet. I was surprised at the effort to get this adorable hotty up, which was a huge turn on for me.

The four went to the restaurant and enjoyed a wonderful dinner. Nat and Lisa, really ate a lot. Clara gave Lisa most of her entrée, which seemed to be something they did often. The play was wonderful too. Nat and Lisa chatted and giggled with each other all evening they were smitten with each other.

Dave and Clara too were enjoying each other’s company. Clara was overjoyed that her friend was so happy and finally really enjoying herself. She really liked Dave too.