(M/F) A night with Jaime (part 1 of ?) | 2016

Jaime and I have a history. We met each other in high school through a church youth group, where all social interaction takes place growing up in Texas. During junior and senior year of high school we dated for a while. Our relationship was my first sexual one, and the first sexual one that she enjoyed. While we didn't ever make it much past short stop, it was an awakening for the both of us. I took the break up harder than she did, but we remained friends. I was, however, half-heartedly chasing her for most of the time we were in our undergrad program at a large state university. Our dynamic was interesting: we would bicker like an old married couple, yet we would seek each other out for advice, emotional support, and to share the juicy details of our lives. We parted ways for our graduate programs, with my acceptance to Johns Hopkins and hers to Michigan State, which gave me the cooling-off from her I needed and allowed me to find a nice girl and begin to settle down. This is not a story about Jaime and I hooking up. This is a story about us shooting the shit back in Dallas a few months before my wedding when we both happened to be visiting our parents. Specifically, the shit about our sex lives...

...

It was a nice change of pace to be in Jaime's mother's good graces. She understandably hadn't been too keen on me while I was dating her daughter, but here she was breaking out the good wine like I was an old friend. "Not too much," I insisted. "I do have to drive back at some point."

"I know, but I'm sure that's hours from now the way you and Jaime get to talking. And there's four years of talking to catch up on."

"Three," Jaime corrected. "We did talk when he met Catherine."

"And now you're engaged. I feel like champagne would be more appropriate."

"I prefer a good red anyway Mrs. A." I took the glass she handed me. "I suppose you'll want to hear about the proposal..."

...

An hour and two glasses later I followed Jaime upstairs, third glass in hand, as her parents retired. It was always a pleasure following her and being three stairs below put me nearly eye-level with the reason why. I gave her a once over while we were climbing, starting at her short, powerful legs years of softball had toned. I paused and grinned on reaching her ass again and resisted the urge to slap it before following her long, slender waist up to her back and bare shoulders, slightly slouched as always. Her dirty blonde hair was tied back high in an attempt to leave her neck exposed to get some relief from the heat that had been midday. I dropped my eyes back down and chuckled audibly. She looked back and cocked an eyebrow at me. "If you really wanted to stay cooler earlier, shorts would have been more appropriate than jeans. Or did you forget what those were while you were up north?"

Half scowl, half grin. "These happen to be my favorite pair of pants. They also happen to be the only thing I've unpacked." She bumped the door to her bedroom open as she said the last and waved at the suitcases. "Besides," she said as she headed toward her bed. "They make my ass look great."

I took a seat in the papasan chair on the opposite end of the room. "One, your ass doesn't need help to look great. Two, who are you trying to impress? Because last I checked your ass had no intest in my cock."

"Looking good helps one feel good." She settled down cross-legged and leaned back against the wall. "Pretty sure that should've been in the psych classes that you took." I shrugged. "Telling stories helps people feel good too, but they save that tidbit for the upper classes. So how did the proposal actually go?"

That drew a hearty laugh from me. "Half-right. What I told your mom was how one proposal went. It just happened that it was the second time she told me yes. Gotta say though, it was the more nerve-wrecking of the two. The first? My cum was just starting to drip out of her when I suggested that if things kept going as well as they were that we make things more permanent. Not exactly something you tell in polite company."

"And we were never polite," she said with a grin. "That sounds much more like you anyway. Keeping it casual and covering your bases for an easy let-down in the event that that's what happened."

"A harsh lesson you taught me." The reminder of my reaction to our break-up made her uncomfortable. "No matter though. If the proposal didn't clue you in, I'm quite over you. Not to say I wouldn't fuck you given the chance."

"Your fiancee?"

"We have an agreement while we're apart these couple of months. If there's anyone you wanna fuck, get it out of your system now because once we're married, it's just the two of us. For a time at least. Threesomes, orgies, still on the table."

"You make it sound like you both have a lot of experience."

"You don't seriously think I wasn't bedding my share of people while being shot down by you, do you?" Silence. "Oh come ON. Give me at least a little bit of credit. I don't look half bad. Tall, fair, athletic, and golden hair is a wonderful combination. And you know my cock isn't anything to scoff at."

"Your build isn't as athletic since you broke your back, but otherwise granted. I just thought..."

"That I was stuck on you? Look, I'd love to fuck you, really. But I'm over you emotionally. And I'll tell you what: I'll be a better fuck than at least 80% of what you've had."

"A bold claim. One that won't be tested."

I shrugged. Was I disappointed? Maybe a bit. "Your loss. I've never had a complaint. And I've never had a one-night stand that didn't want another round with me."

That boast caught her attention. "Well, it's not like they would tell you if they had a complaint. They'd just tell their friends. But as for the second part... there is something to be said for that. Who was your first?"

"My first fuck or the first hook-up after you?"

"They weren't the same?"

I smiled. "I guess we'll start at the beginning. Remember Marsi?"

...

Marsi was a year older than me and had been away at college when Jaime and I broke up. So when she openned the front door of her house to let me in while she was in town over Thanksgiving, she was expecting to hear news of how Jaime and the old group of friends she used to run with were doing. She seemed genuinely sorry when she heard about the break-up, and was kind enough to let me vent out my heartache on the couch before we settled in to watch the movie she had picked out. It was odd for her to be serious rather than her usual bouncy, energetic self. I mentioned as much to her after I gave her my sad story and the smile her round face usually wore came back. "I didn't want you to think that I don't feel for you," she told me as she brushed a strand of her shoulder-length brown hair behind her ear. She hit play on the Wedding Crashers and settled up next to me. Had it been any other person, the closeness would have been an indicator of what was to come, but Marsi had always been a touchy-feely type.

We watched in silence until after the montage of topless women falling onto beds finished. I felt slightly awkward about having just watched that with a platonic friend, so I felt driven to say something. "Nice tits on a few of them." I turned to look at Marsi with a sideways grin and she snapped up her eyes to catch mine. "Or did you not see them?"

"Oh no, I did. I was just... worried about how you would react. I mean, you guys broke up in September you said? It's been a while since you've had any stimulation."

"There are ways..." I left the thought unfinished for a moment. "Or have you learned nothing at college?" She actaully blushed a little at that. Maybe I had gone too far? That little bit of banter wouldn't have bothered Jaime.

"I've learned a bit more than you seem to think. I also went in knowing more than you give me credit for." I glanced over at my friend. She hadn't really registered as a sexual being to me previously, but there was a defiance in her tone that sparked something in me. Marci was a short girl, barely over 5 feet tall, and would be best described as "compact." She had the slightest of curves toward an hourglass form and a very cute face. And she had that stereotypical bit of fire that is associated with shorter girls.

I made a point to keep my voice flat. "Oh? Do tell." Shit. The slightest suggestive tone had slipped through my effort, and her grin told me she had caught it.

"Well, there is actually a trio of boys out to get me." She drew a leg up on the couch and turned toward me. "Two of them are rather cute. The third isn't as much, but he has the best sense of humor to make up for it. He's actually the one that received my first blowjob, which he said didn't seem like my first one. I did blow one of the others too, and he gave me a few pointers which they've both benefitted from."

I felt my cock starting to rise. While there were ways for a guy to take care of himself, it had still been some time since I had a girl say anything sexual toward me. I avoided shifting too much and put my hope in the fact that the darkness of the movie room would hide my excitement. "Dare I ask about those pointers?"

She put on a devilish grin this time. "Oh, I don't know that they would apply to you. They were tips on how to deal with men that were larger."

Her teasing drew a laugh. "You're speaking about things you don't know about and making a fool of yourself. Besides, with your size 4 inches would seem large." She punched my arm. "Oh come now, do I lie? Your boobs are about B cup right? But they look large on your frame. With those cute little hands of yours, any cock would look bigger than it was.

"Shall we put that to the test?" She threw a glance at my lap. "We'll see how small my boobs feel in your hands and how large your cock is in mine." If she had still been looking at my lap she would've seen my cock jump. Was she serious or was this a stab at my sexual vulnerability since I had stabbed at her height? I looked into her eyes, looking for curiosity. What I saw was hunger. That was more than signal enough for me.

I drew my knees under me and pushed her over onto the couch. I brought my mouth within an inch of hers. "Why don't we?" I breathed before brushing my lips momentarily over hers before sliding down to kiss her neck. Supporting myself with one hand, I brushed the fingertips of the other down her side, drawing a satisfied hum. I rested them when I felt the warmth of exposed skin between the bottom of her shirt and her jeans. I felt her hands go straight to my belt buckle. "One question," I said as I slipped my hand under her shirt and around toward her stomach. "Is this a new desire?"

She undid my belt and snap in one quick motion. "No." She placed her hand on my cock through my pants and I slid mine onto her tit over her bra. We caught each others' eyes and grinned. "Larger than I thought," she said, "but not the largest of the three."

"Large enough for your pointers I dare say. And you're larger than the handful I thought you were." I sat her up and pulled her shirt off, breaking her contact with my cock. Her hands went straight to removing my shirt once she was free of hers. I reached for her tits again, but she caught my hand and pulled it down to her crotch. I put a pressure on her, but otherwise rested it, while my other hand snaked around her back and unclasped her bra.

"You don't need what's in your pants to impress a girl," she told me. "You just need to show them you can do that." I chuckled and took in the sight before me. "You going to just stare, or were you planning on doing something here?" Taking the invitation, I dove face-first into her chest and knocked her onto her back again. I took her nipple in my mouth and she arched her back, pushing her crotch against my hand. I began massaging her other breast with my hand as she undid her pants. "Show me what you know first," were her instructions as she moved my hand to slide her pants off.

I replaced my hand between her legs and felt her panties were still on. Taking that as an indication she wanted just my hand and not my mouth down there, I continued to worry her nipple with my tongue while I pulled her panties to the side and started rubbing the outside of her slit. Her hair there was short enough that she must have at least trimmed, but it had been some time since she had a close cut; just long enough to get caught in your mouth, but not long enough to interfere. I switched the breast my mouth was working and slid a finger into her folds. Something had turned her on fast because she was plenty soaked. I effortlessly slid a finger in and began slowly fucking her with my hand. She moaned at that and pulled my head closer to her chest.

When I slid the second finger in a few minutes later, I sat up and began the "come hither" motion on her g-spot that Jaime had so loved. I took my second hand down and began to lightly circle her clit. Her breath caught and her eyes caught mine. "Make me come. Now." I made the cirlces tighter so I was rubbing her clit directly. She arched her back again, making me lose my place momentarily. When I found it again, I put more pressure on her clit and resumed circling. It was a matter of seconds before the combined stimulation from inside her and on her sent her over, moaning and bucking her hips.

"Lose the pants," was all she said once she recovered. I undid the zipper and slid the pants and boxers off at once, eager for my first blow job. My eagerness faltered a little when I realized I hadn't trimmed my pubes since the break up. Marsi must have noticed my uncertainty. "Weren't expecting to have to be cleaned up? Not a problem. One of the boys at school doesn't groom at all. Now, let me show you those tricks."

She put her hand on the top of my shaft and held me high. "You do look even bigger in my hand," was the last thing she said before taking my balls in her mouth. A few moments of licking and light sucking later, she slid her tongue up the underside of my shaft, closed her lips over my head, and slid her mouth down behind her hand until I hit the back of her throat. It was my turn to moan, and I could feel her grin around my cock while she held it deep. She dropped her hand to the base and came up for a breath before going back down. I felt her throat around the tip of my head for just a moment before she came up coughing. "Alright, you're about as big as the larger of the boys."

I knew 7 inches was a little above average but a far cry from huge. Even still, her saying that made me feel like a giant. When she went back down on me, she began a steady up and down bob about halfway down my shaft with her hand stroking at the same pace. Every now and then her hand would brush the bottom of my head and draw another gasp or moan from me. After a while she caught on and regularly let her hand come over my head. It wasn't long after that I moaned that I was coming. She took her mouth off and vigorously stroked me as I began shooting. The first rope landed on her arm, but she redirected and the rest covered my stomach and chest. "Next time I swallow," she grinned. "But only if you go down on me first."

...

"And did you go down on her?" Jaime asked.

"It was a few months later, when I was touring her university, but yeah. And she kept her end of the bargain too."

"Good girl. That must have been a great pitch to go to her school. And yet you chose to follow me."

"You being there had nothing to do with it. I wanted a larger school. And her school had almost no science program. Didn't stop us from hooking up a third time before she went overseas."

"I thought she was engaged before she graduated."

"Where do you think Catherine and I got the idea to get one last hurrah of hedonism out before settling down?"

"Three blowjobs isn't hedonism."

"Girly, we've barely scratched the surface."

"Yet you're offering no more details."

"That's because you still have to tell me about your first blowjob."

Jaime pointed at my empty glass. "We need more wine for that."

"That was the last of it. Get the liquor, I'll mix."