Dean and Summer’s Relationship

For Dean and Summer’s relationship to work out they needed to change only being able to see each other after Summer’s shift at the restaurant. Dean had a pretty set schedule during the week and Summer had to work weekends because that is when she gets the best tips at the restaurant. Ultimately Summer changed her work schedule so she didn’t work everyday but now that meant some days she had to work much longer just so she could have a free day. At least now they saw each other outside of her work.

The buildup and progress of their relationship was slow, very slow, but that didn’t matter to Dean as long as Summer was his and no one else’s. A month into their relationship Summer and Dean had only kissed not even making out at this point but they sure talked a lot which in turn makes certain things come up.

Turns out Summer is a virgin. On top of that Dean is her first serious boyfriend, she hasn’t done much more than kissing and making out with someone before. She did say a guy in high school felt her up once but over her shirt. Dean was very surprised by this, Summer had an amazing body and a beautiful face, how could she be a virgin? Well it turns out that it is by choice and this is where her religious background holds some value in her, she doesn’t want to have sex until marriage. She also has never masturbated. She is the reserved type so it makes sense why things are going so slowly between them.

All this is okay with Dean of course. He isn’t having sex or anything of that nature but he’s okay with it, he does jerk off a bunch to make up for not getting anything with Summer. Good things take time and Summer will be worth the wait.

A month later, so now two months into the relationship Summer celebrated her 21st birthday. She did not have any interest in drinking though, she just wasn’t into ****. Dean was okay with this of course, at least he would always have a designated driver! Their relationship has now grown to making out, for someone without much experience she was a very good kisser.

Six months in now, Dean and Summer’s relationship was going strong. They enjoyed each others company, it was a pleasant change for Dean as this relationship hasn’t been all about sex. Dean finally got to feel Summer’s amazingly large breasts, over her shirt of course. In fact he hasn’t seen much of her body, she’s always wearing very reserved and covered clothing, not even showing cleavage. You’d think with a name like Summer she would like the Summertime but she didn’t care for it, she wouldn’t be seen wearing a bathing suit.

It’s now been a year since Dean and Summer started dating, today was that special day. Dean texted Summer when he woke up I’m the morning, ‘Good Morning beautiful!’ He got out of bed to get ready for his workday. He showered and headed downstairs for some breakfast. His phone started ringing, Summer was calling, she must have just woken up.

“Hey Summer!” Dean answered the phone.

“Mornin' good lookin'! Happy anniversary, darlin'! I'm so dang excited to see ya later! Dinner is gonna be a hootin' and hollerin' celebration!” Summer giggled.

“Hootin’ and hollerin’?” Dean said in friendly mocking tone.

Summer laughed at herself, “I apologize, darlin'! My Oklahoma accent tends to sneak out when I'm all fired up!”

“Don’t worry, you know I like your cute accent,” Dean says.

“Thanks, hun! I'll catch ya later, bye now!” Summer said.

Dean had breakfast and went to work, Summer headed to her shift at the restaurant, later they will meet for their anniversary dinner.

Dean and Summer met at a pretty nice restaurant, nothing too fancy, Summer didn’t care for upscale ritzy type places. This place had a good steak so Dean was happy and he didn’t have to splurge for their anniversary. Dean brought some flowers and gave them to Summer, she appreciated them, gave Dean a kiss and they walked into the restaurant holding hands.

The hostess could clearly see they were here to celebrate something and asked, they happily told her it was their anniversary while she led them to their table.

The waiter brought champagne over to their table, “I hear you’re celebrating an anniversary? Here you go, these are for you,” he said while putting two champagne flutes down and pouring the first glasses and putting the bottle on the table. “Well, bless your heart! Ain't y'all just the sweetest! Thank you kindly for the champagne. Cheers to our anniversary!" She said while Dean and her clanged glasses. While the waiter stepped away Summer pushed her glass towards Dean, she still wasn’t into drinking and Dean happily would drink it for her. The rest of the dinner was pleasant, the food was good and they enjoyed each others company. The restaurant even gave them a complimentary dessert!

Dean and Summer exited the restaurant holding hands just like they entered. Dean was now a bottle of champagne deep which made him more loving but also a little handsy. They kissed a little and his hands wandered to her ass. Dean usually wouldn’t be so forward with Summer but he had some liquid courage.

“Well, I reckon it's 'bout time for me to mosey on back home now,” Summer said, she didn’t look happy to be leaving.

“Come over, let’s hang out, it’s our anniversary after all,” Dean said, he had some dirty thoughts brewing.

“I probably shouldn't swing by, darlin'…” Summer reluctantly says, maybe she’s on to Dean having impure thoughts. “But…” Dean stutters.

“Are ya okay to drive? Maybe I should take ya home?” Summer says. Dean nods, he wants to spend more time with her, he knows he can drive, it was only a little bit of champagne but if this will get her to his house then sure.

Dean got into Summer’s car and she drove them to Dean’s house. She stopped in front of the house and gave Dean a kiss.

“Aren’t you gonna come in?” Dean asked her. She was a little hesitant, “Um, sure darlin’” She parked her car and they both walked in, she seemed a bit nervous and a bit uncomfortable but Dean’s thoughts were elsewhere, he was horny.

Dean and Summer got into the house and he lead her to the couch. He initiated the kissing and they started to make out, he started touching her body all over which is nothing more than what they already have done. Summer could see where this was possibly leading and pushed away and stopped Dean, “I don’t want to have sex Dean. I reckon I ain't quite ready for that, darlin'.” Summer said, “I reckon I want to wait, take things slow, ya know?”

Dean was understanding, “I know you want to wait, maybe I could please you in a different way?” He said while moving his hand up her thighs towards her pussy. She put her hand on his hand stopping him, his fingertips resting near her pussy, he could feel her warmth. Although she was saying no, her body was feeling some type of way. “I’m not ready for that either,” she said, “But maybe I could do something for you?” She said looking at him. Dean was surprised by her but happy, “You sure?” He said. “Yes,” She smiled at him.

“Could you…” she gestured to his pants. Dean was extremely excited, he started unbuttoning his pants as quickly as possible. Pulling them down with his underwear springing his hard cock. Summer didn’t reach out right away, she was hesitant, she’s never done anything like this, this is the first real cock she was seeing in person. Dean could see the curious look on her face, she was analyzing his cock. She reached out touching Dean’s cock for the first time, touching her first cock ever. She wrapped her hand around his cock, “Do I just…” she said while starting to stroke him up and down. “Yeah, just like that.” “I’m sorry, I don’t really know what I’m doing…” she said. She looked like she was concentrating hard on what she was doing. Dean helped her and guided her, “You’re doing just fine honey…” Dean was enjoying Summer touching him, he hasn’t had someone else touch his cock in quite some time. “Faster, Faster…” Dean moaned. Summer jerked him off faster. Dean was close, “I’m close, keep going…”

Dean let out a groan and started to cum. This surprised Summer as she let out a little yelp and let go of his cock. He continued to cum, “No don’t stop…” he said. Summer quickly grabbed his partially cum cover cock and started jerking him more until Dean told her that was enough and to stop. Dean thought, not bad for her first handjob besides the little bit of a ruined orgasm.

Summer got up and ran to the bathroom to wash off her hand that was covered with cum leaving Dean to clean himself up.

She returned to Dean pulling up his pants, “How was that?” She said. “Great, honey! Especially for your first handjob!” He said. Summer shyly smiled, “is that what that’s called?” She was slightly amused with herself doing something so new. “I reckon we should only do that on special occasion, yeah?” She said. “Oh of course honey,” Dean said.

“I think, it's time for me to mosey on home as well,” Summer said. “No, you should stay!” Dean says. “I don’t know…” Summer said. “I won’t try anything else, promise!” Dean said. “Well alright then,” Summer said.

Dean and Summer went upstairs and got ready for bed. Dean let her borrow an oversized t-shirt and shorts. Summer got changed in the bathroom, guess tonight is not the night he will see her naked. She slipped into bed, and they talked for quite some time. Summer yawned, she was getting tired and it was time for them to sleep.

“Goodnight, darlin’,” Summer said as she turned away from Dean. “Goodnight Summer… I love you.” Dean said. It was the first time he said to her he loved her. Summer turned over and kissed Dean, “I love you too.” She turned back over. Dean laid on his back smiling.