The First Time Is Never Perfect

The First Time Is Never Perfect. (M/F, Fiction)

What to wear, oh what to wear.

It had been 2 nights since Karen and Doug had made love for the very first time. Even though Karen had not shared her innermost feelings with him, for once, she had actually enjoyed her lovemaking, because she hadn’t thought too much about it as it proceeded (OK ladies, that was a cheap shot, now back to the story ;-) )

Tonight was going to be different. Doug was coming over at 9pm to pick her up, but Karen really didn’t want to go anywhere. Tonight she was going to let him know what her turn on was, she felt comfortable knowing that she would be able to share it with him.

It had taken a while for the couple to even get together. Karen had a self confidence issue, never thinking she was ever attractive enough to guys, and deeply traumatized daily because of her weight issue. Sure, she had tried every diet known to man, but the true cruel twist of fate was the post diet routine. Starting at 160lbs, she would lose 8lbs, come off of the diet and gain 10lbs. Life really sucked when she was alone, thinking that there was never going to come a day when anyone could love her. Knowing the usual routine of guys, Karen felt that she was never going to be anything more than the drunken one night stand, and that never appealed to her anyway, she had way too much respect for herself to allow that to happen. It was the most depressing feeling she had ever felt, and she spent many a night crying herself to sleep because of it.

When she had met Doug, the first thing that caught her attention to him was the flattering comments he would make to her about her clothing, lord knows it made her feel good, it would almost make the one hour she had spent in front of the mirror, trying on different outfits until she found the one that she felt hid her weight the best, almost seem worth it.

Tonight she was prepared. Black had long become her favorite color to choose for her clothing, but tonight she was going to be brave and relax her inhibitions a little bit. Amazing what a few kind words will do for a gal. In her lingerie drawer, Karen removed the sexiest piece of clothing she had saved for this special day, a matching white satin camisole and tap panty set. While it made her feel really sexy, it was still too much for her to wear complete. So instead of the camisole, Karen instead swapped it for a more conservative dark blue negligee. But sexy, oh boy did she feel sexy.

Doug arrived on time as usual, somewhat surprised to find her still in a housecoat. As Karen let him in he did not get more than 3 feet into the apartment before she had grabbed him and began to passionately kiss him. The deeply intimate moment was enhanced when his hands moved inside her housecoat and he began rubbing her back and buttocks through the silky material. Doug’s back was to the wall and Karen pushed hard against him, feeling his growing manhood press into her stomach, giving a little wink, Karen moved back slightly and used her hand to rub his erection through his pants, it didn’t seem that the two of them were going out any time soon.

Karen led Doug by the hand and walked to the living room. They went to the couch and Karen almost pushed Doug down onto it. Shedding herself of her housecoat, she then reached down and began to unbuckle his pants, slowly drawing them off of his muscular legs. When they were off, Karen straddled herself across his legs and resumed the passionate kissing they had started in the hallway. Her weight issue no longer was even an issue as she grinded her pelvis into his swelling erection. Doug’s hands explored her fully as Karen kissed his neck and ears. Taking what she now saw as the perfect opportunity, Karen whispered delicately into his ear “Spank me, Doug”.

This was a request that Doug had never had of him before, and half blew the suggestion off, but Karen pulled back from him with a sexy look on her face and lifted her right leg off of him to join the other on his right side. Karen almost let the moment ruin itself for her when she laid herself across his lap, she had tried to lift her negligee as she went over, but it seemed to get snagged somewhere and left only one side up. While the first thought was to self deprecate herself over her weight, she just about managed to keep the mood and casually finish the task once she was fully over.

Though Doug was willing to oblige her, he found himself in unfamiliar territory. Thinking quickly he stammered out “So, you’ve been a naughty girl have you?” This was the last thing that Karen wanted to hear and she pretty much blushed at the comment. Turning her head to face him, she coyly said “Please Doug, no baby talk, just spank me” Looking down, Doug surveyed the white tap panties below him and began to gently tap the seat of them. Karen tolerated this for about 15 slaps but was quickly frustrated, this wasn’t what she had hoped for at all, summoning up all the courage she could muster she said to him again “Don’t be afraid, Doug, please. Hit me harder than that, much harder” Doug was totally unsure of himself, but he did start to smack just slightly harder, watching all the time to see if he was hurting her at all, which was something he really didn’t want to do. Karen laid her head on her arm and enjoyed as much as she could what was happening, thinking all the time that she wanted him to spank WAY harder, but at the same time, not wanting to scare him off as some type of freak.

Realizing there was no chance he would do it himself, Karen reached back and pulled her own panties down. Doug never did spank any harder, but Karen at least was getting some attention to her bottom and laid there enjoying the soft smacks as much as she could. One surprise really shook her when Doug all of a sudden stopped the spanking and moved his hand in between her legs. A mixture of joy and surprise overcame her all at once and she allowed his fingers to work inside of her. Knowing that after the 80 or so mild smacks was all she could probably hope for tonight, Karen climbed herself back up and once again straddled him on the couch. As she began kissing him and feeling the first sign of penetration from Doug, Karen thought to herself, well it wasn’t what I wanted, but at least it is a start, I am sure he will make a fine spanker in the weeks ahead. Then she allowed herself to become totally immersed in yet another passionate lovemaking session, and this one was with a slightly pinkened bottom, what could be better? What more could a girl ask for?

Richard Windsor.