A Surprising Development Ch. 02

Kelly's Apartment

Carrie rolled over and put her arm around Kelly. Pulling her close she loved the feel of her naked body against Kelly's in the morning. It was a great way to start the day.

Carrie met Kelly on the first day she arrived at college. Roommates, they hit it off right away. Both were education major. It seemed so easy. This year they decided that an apartment would be better in terms of saving money and just be better.

Carrie was from western Massachusetts and unlike Kelly, came from a large family. She was outgoing and at ease with people. Carrie was surprised to hear that Kelly was an only child as her few experiences with them always found them a little reserved. Not Kelly. She was friendly and open right from the start. They hit it off right away.

Carrie was Kelly's opposite in looks. With short dark brown hair and hazel eyes, Carrie had a fuller figure than Kelly's swimming body. About Kelly's height, her breasts were larger and her hips broader. She had no trouble attracting boys but never found one she was very serious about.

There was something else too. Carrie had always been curious about being with another girl. She had thought about it but never ventured too far in that direction. She had kissed a girl, her best friend in high school, but never took it the next step. She found the kiss exciting and it made her more curious. One thing that held her back was not being real sure how to take that next step. Meeting Kelly showed her how.

As with a lot things with Kelly, it just started soft and easy. One night while they were sitting, studying, Carrie decided to ask, "Kelly, have you ever kissed a girl?"

Kelly put her glasses down and closed her book. "Yes, why are you asking?"

"I don't know. I'm just asking," Carrie replied.

"Yes, I have. Have you?" Kelly asked in return.

Carrie blushed. "Yes just once."

Kelly got up and walked around the table. She softly put her hands on each side of Carrie's face. She bent down and lightly kissed her on the lips. She pushed a little harder before breaking the kiss and standing up. "Ok?"

Carrie just nodded. The kiss felt fantastic. It sent tiny tingles through her. She wanted another one.

It was as if Kelly sensed it too. She bent down again and kissed her. Only this time she pushed her tongue into Carrie's mouth. Carrie offered no resistance. Kelly moved her hand gently behind Carrie's head and lightly held there. Carrie had no idea how long the kiss lasted but this time the tingles were stronger and went right to her pussy. She squirmed in seat. When Kelly stepped back, Carrie felt a little lightheaded.

"Did you like it?" Kelly asked, smiling.

Carrie stood up and wrapped her arms around Kelly. She kissed her, opening her mouth and sucking Kelly's tongue into it. She pressed her body hard against her. Leaning back, Carrie said, "Does that answer your question?"

Kelly took Carrie by the hand and led her into the bed. That night Kelly taught her how it felt to be made love to by a woman. Never had she experienced such intense feelings. She lost count the number of times she came. It was so good that they skipped class and stayed in bed all the next day. When they weren't making love that day, they simply talked.

Kelly confessed that she was bi- and felt just as comfortable making love with a boy or a girl. Her parents, especially her mom, were very open about their relationship and had passed that along to her. She didn't sleep around and didn't want to. She was sure she would find the right boy but until then she was happy with her choices.

"Good morning, Kel," Carrie said kissing the back of her head. "Sleep well?"

"Like a log. You?"

"Yes and you were out like a light," Carrie said sitting up. "You have been sleeping like that every night. You seem very happy. Anything to do with that new boyfriend of yours?"

Kelly rolled over and sat up. "Might be."

"So when am I going to formally meet him. You know, a dinner or something?"

Kelly thought for a moment. "How about this weekend?"

Carrie shook her head. "No good, I have to go home and help my parents at the store. It has been hard getting help so I said I'd help out. Hopefully this will be the last weekend."

"Ok, then plan on the following weekend," Kelly kissed Carrie then hopped out of bed. "Let's go, don't want to be late for class!"

***

At the School Library

Jack put his pen down and looked across the table at Kelly. "God she was beautiful," he thought. "He was one lucky guy!"

Kelly was sitting there and doing her work. Even in the simple setting, Jack knew he was lucky to call her his girlfriend. Her silvery grey hair shone in the light and cascaded along her face down to her shoulder. Her blue eyes sparkled behind her glasses which somehow added to her looks. Her skin was flawless and her smile, well it just blew him away when she did.

Her figure was the tight swimmer's body. There wasn't an ounce of fat anywhere even though she complained that her ass was too big. How could he answer that age-old question when just looking at it could make him hard? Her breasts were larger than the usual size for swimmers but not too big. She thought they slowed her down in the water.

As he looked at her, he smiled. "She is so God damn hot!" he thought.

And that was a problem. Not a bad problem but a problem. Wearing panties always excited him and even though he didn't walk around with a hard-on, his cock was always swollen. On the days he was able to spend with Kelly, like in chemistry or even lunch, just being with her caused it to harden. Worse yet if he started to daydream about him!

She had bought him enough pairs to wear one every day. They even made a little game about, having her guess the color and style. She said she could guess by the way he was acting. It did bother him that he was walking around with a bugle in his pants so one day he wore his old boxers.

Kelly sensed it right away. "What's wrong, sweetie?"

"Nothing," Jack replied defensively.

She moved a little closer. "You seem a little grumpy today. Everything alright?"

"I'm fine, Kelly, just leave it, will you?" Jack snapped.

Kelly backed away but she was determined to find out the problem. Later as they walked quietly together, she quickly stepped behind him. Pulling on his waistband, she made her discovery. "Aha," she exclaimed, "Baggy old boxers! No wonder you are cranky. You know what we said."

He spun around. "Look, I don't need to wear panties every day. I can do what I want. Now leave it, will you please?"

They walked to the cafeteria and ate their dinner in silence.

Entering Jack's dorm room Kelly went straight to his dresser. Opening the top drawer, she said, "Ok, Oscar the Grouch, we are going to solve this right here!" she began pulling out all of his boxers and briefs. "All of these have to go! Especially these tightie whities!" She held up a pair of nylon tied dyed tiny briefs. She looked at him and smiled. "These we can keep but the rest has to go" Kelly turned to Jack. "Now take off your pants. Boxers too."

Jack did as he was told and now stood there naked from the waist down.

Kelly walked over and put her hand on his cock. She began stroking it. "Now we know how much better you feel when you wear your panties, right Jack?"

Jack nodded as his cock grew in Kelly's hand.

"You're not grumpy at all." She stroked him faster. "This will make it easier for you to choose, right?"

Jack moaned as he nodded.

"Good," she said letting go off his cock and stepping back. "Pick out a pair and then we need to go to library."

So here they were at the library, studying. Other times they did this it was very productive but tonight was different. Jack couldn't concentrate as he kept looking over at Kelly.

"What?" she asked looking over her glasses.

"I was just thinking how beautiful you look and very sexy in those glasses," he said quietly.

Kelly blushed and looked down. "Thanks, now you better get to work."

Jack tried but he couldn't. His cock stirring inside his panties wouldn't let him.

"Now what?" Kelly said, leaning across the table. "I'm trying to study here."

Jack slipped a note across the table to her. She picked and read it. "I want to do you in the worst way."

"Here?" she whispered.

"Can't use my room. Roommate is there," he whispered back.

"Carrie is back in the apartment," Kelly softly answered.

Jack slumped back in his chair. He shrugged his shoulders. "Oh well."

Kelly took off her glasses and looked around. She stood up and offered Jack her hand. "Come on."

As soon as the elevator doors closed, Jack started kissing her.

"Slow down, sweetie," Kelly said laughing, "Not in here!"

The elevator stopped at the top floor. When the doors opened, it was pitch black. Jack looked at Kelly who motioned for him to come on. As they stepped out, the lights came on. "I used to work in the library as part of my work studies. Not too many people come up here." She grabbed Jack's hand and led him through the stacks.

She stopped at a table and hopped up on the edge. Hiking her skirt up, she spread her legs. She put her hands on Jack's shoulders and pulled him between them. Lowering her hands, she began to unsnap his pants.

Jack began to nibble Kelly's neck causing her to squirm and sigh. His hands unbuttoned her blouse and he reached in to caress one of her breasts. He could feel her nipple harden.

Kelly's hands moved faster as she pulled Jack's pants down. She reached inside his panties to find him hard and ready. "Fuck me, sweetie," she whispered in his ear as she nibbled on his earlobe.

He reached between Kelly's legs and found her panties wet from excitement. He stepped back causing Kelly to look at him in surprise. He pulled her closer and flipped her onto the table, face down. He lifted her skirt and pushed her panties aside, expose her moist and open pussy. He stepped forward and easily slipped his hard cock into her.

Kelly moaned as he entered her. She didn't realize how much she needed his cock. Every time they made love it was good. This time it would be no different. She grasped the edge of the table and began to move in rhythm to Jack's movements.

He didn't know if it was the surroundings or what but her pussy felt amazing around his cock. It was like his cock was in warm velvet inside an iron glove. Each stroke sent amazing sensations through his body. He felt his balls begin to tingle. "Oh fuck," he quietly moaned.

Kelly felt it too. Each stroke sent waves of feelings from her pussy to each part of her body. She lifted her head off the table and began to slap her ass against him, taking his cock as deep as she could. Hearing him moan caused her to respond, "Fuck yeah, sweetie, cum for me!"

That was all Jack needed. He grabbed her waist and pulled her tight. He began to cum inside her pussy, filling it. "Oh fuck, baby!" he groaned.

Kelly came right behind him. She could feel his cock spasm inside her pussy causing her to cry out, "Oh God yes, yes" as she came.

Jack stepped back and sighed. "That was amazing babe," he said softly.

Kelly rolled over and smiled. "Yes it was, sweetie. I love making love to you!" She leaned forward and kissed him. "I think we need to get out of here before someone comes up here. Besides I still have some studying to do."

They both laughed and holding hands, headed to the elevator.

***

That Weekend

It was the weekend and it was time for "Jackie" to go out. Jack had to admit that the more times he dressed as "Jackie" the more comfortable he was becoming. Kelly was right about the panties too. Ever since she cleaned out his drawer of his own underwear, he was enjoying just having panties to wear. It was one less decision for him to make. She tossed the one remaining boxer pair and left him just the one pair of nylon briefs. He hadn't worn them since that day.

He had to thank Kelly for all her support. It was almost as if she knew he wanted to do this. She kept telling him she understood but never explained how she did. He knew he never would have done this on his own but with her support and caring, he knew it was right for him. When they went out together as "Jackie" and Kelly, she was always giving him pointers to make it easier. She joked that the next big test was going to be heels but she was sure he pass the test.

Saturday morning they awoke at Kelly's apartment. Because Carrie had been away every weekend helping her parents, it worked out well. Friday night dressed as "Jackie" Jack and Kelly would go out together. Sometimes it was for dinner at a local place and then go to some event on campus. Other nights they would just stay in. Today they were going into Boston for the day. They planned on shopping, eating at the North End, and just taking in the sights.

Kelly helped him get dressed and today she decided that a skirt, a blouse, and a sweater would like great. She also suggested some tights as the late fall was beginning to turn cooler.

"It might get a little drafty with a skirt but I think you should get used to it," Kelly explained to him.

Jack laughed. "Two years ago I re-enacted the 42nd Black Watch at Ticonderoga. They wore kilts." Jack had been working with the National Park Service since high school. He portrayed a British drummer boy most of time and had plans to use his degree to work full time for the Service.

"Really?" Kelly asked. "Is it true they didn't wear underwear? Did you?"

Jack smiled, "No, they didn't but yes I did. Some of our unit didn't though."

"Hmm," Kelly said, tapping her finger on her mouth. "Perhaps we need to find you some plaid panties."

As they rode the T into the cities, Kelly had to remind him to sit down and not offer his seat to any lady. It was little things like that he needed to work on.

Kelly held his hand on the ride in. It wasn't that long but it gave her time to think. She couldn't believe how all this was coming together. She had a boyfriend who was more than she could ask for but she somehow had a girlfriend too. She talked to her mom every week and told her everything that was going on even Jack dressing as a woman. When she told her Jack was being more confident and comfortable when dressed like "Jackie", her mom told her to be patient and supportive.

"Be there for him. Don't get angry," her mom said, " Don't push. He'll be ready when he is ready. Number 1 thing is to make sure knows you will be there."

"Mom, I thinking of asking him to move in with Carrie and me next semester," Kelly confessed.

"Does Carrie know all about this?" her mom asked.

Kelly replied, "Not yet. She knows about Jack but not about Jackie."

"I think you better work that out first, sweetie. I trust you and I know you'll make the right decision."

"I still want you to meet him. I know you'll like him as much as I do."

Jack tapped Kelly on the shoulder causing her to flinch. "You ok?" he asked, "Our stop?"

"Yes, time to go," she replied getting up.

They had quite the day together. They shopped in Faneuil Hall and watched some outstanding street performers. Kelly bought a new blouse and convince "Jackie" to buy a rather form fitting one for herself. "You can wear it as an undershirt if you want," she said.

They were having so much fun that the day seemed to fly by. Realizing it was after lunchtime, Jack suggested Legal Seafood. It was a little expensive but he hadn't taken Kelly any place like it. "My treat."

"Ok but there is one more stop I want to take you," Kelly said leading the way.

She stopped in front of Victoria's Secret.

"Here?" Jack asked stopping in his tracks.

"Sure, why not? I want to get a few things," Kelly said reaching for his hand. "It will be fun."

Jack stood his ground. "I don't think I should go in there."

Kelly gave him a funny look. "Why not?"

"Two reasons," Jack began, "You saw my reaction at Kohl's when you handed me the panties. Second I know I will start thinking about you wearing some of those things. Not good."

She smiled. "Come on, we'll be quick and nothing will happen." She leaned closer and whispered, "You're so sweet."

The two girls entered the store and immediately the sights overwhelmed Jack. He stayed close to Kelly, not letting his mind or eyes wander.

Kelly picked out two panties and held them up for him to see. "What do you think?"

He couldn't tell her what he thought. The panties were thongs and there was barely any material to them. A picture of Kelly in them flashed in his mind. He quickly started thinking of the 1998 Yankees' line-up. "They look good," he stammered.

"Good," she said, "Hey look at these!" She picked up a pair of red plaid bikini briefs. "How about these for you?"

He didn't have the heart to tell her it was the wrong plaid. Instead he nodded and said, "All set?"

Kelly took his hand, "One more thing," and they headed to the back of the store to where the sleepwear was. "You can't walk around the apartment naked so you need a set of pj's. I was thinking a chemise and briefs would be just right. Any style or color you like?"

"Good Lord," he thought as he felt his cock stirring, "So many choices!" He stepped forward to look. He took a light blue satiny set from the selection. As he did, Kelly moved behind him and lightly grabbed his ass. She whispered in his ear, "You'll look pretty hot in that."

They made their purchases and headed to the restaurant. The pink shopping bags announced to everyone where they had been.

The food was amazing and they ate outside in the sun, which allowed them to people watch. Jack made up stories about some of people as they passed, wondering if the blonde in tight jeans was really a spy. Kelly decided she was really an office manager who on weekends was an expensive escort. Jack laughed as he said he liked her story better.

"I wonder what people are saying about us?" he asked Kelly.

She put her fork down and thought for a moment. "They are saying there are two beautiful young ladies who definitely are enjoying themselves. They are waiting for their rich boyfriends to drop by in their expensive car and pick them up."

Almost on cue, a Porsche convertible pulled up, driven by an older man. He appeared to be about forty. He looked around and when he made eye contact with the two girls, he smiled and nodded. He then drove off.

Jack and Kelly looked at each other and then burst into laughter.

"So it looks like we'll be heading back to the college now?" Jack asked.

"It's still pretty early," Kelly answered. "Let's get on the T and get off at Harvard Square. See what there and maybe hang out for a while. Get some ice cream."

Jack agreed and so off they went. They got off at the Square and browsed the different stores. They didn't buy anything but had a good time just looking.

"Want to get that ice cream now?" Jack said spotting a Baskin-Robbins.

"Not yet!" Kelly looped her arm in Jack's nearly pulling him off his feet. "Let's go in here!" Here was the sex shop Good Vibrations. Before he could object, they were through the door.

"Wow" Kelly said, "Quite a place."

The store had everything from vibrators to dildoes to things they both had no idea what they were for.

"May I help you young ladies with anything?" a young woman clerk said approaching them.

While Jack said nothing, Kelly quickly answered, "Just looking but what do you suggest?"

"What are you looking for? Beginner or looking for something to add? Boyfriend?" The woman glanced over at Jack. "Or girlfriend?"

Kelly smiled, "A little of both"

The woman and Kelly began chatting as she led her over to some toys. Kelly laughed at something she said as Jack remained behind. The store made him uncomfortable in more than one way but he slowly walked around. He had to admit it was quite eye opening. He also was surprised at Kelly. She seemed quite at home talking and looking.