The True Tale of my First Lover

By castlequeen

Original link:

Tags: oral sex, kissing, cunnilingus, orgasm

Added: 24 Dec 2009 Views: 9724 Avg Score: 4.38

The night I first learned how great sex could be!
I'm not a baseball fan. I'm tired of striking out. I'm 19, a college freshman, holding down a 4.0, and I'm still a virgin. I am such a loser.

Maybe I'm not a loser, but I'm certainly not popular. I got asked out on my very first day on campus, but it was really a flyer to a frat party, and the guy said "make sure you bring some cute friends!" Ouch. I only knew one girl from my high school, and she went with me, except she's gorgeous and she got swept off the second we got in the door. I spent the evening wandering around and the most interesting thing that happened was two guys discussing the most recent NASCAR race. Once they realized I knew as much about racing as they did, I was cool. One of the guys, really. When I asked one of them to dance he remembered an urgent appointment elsewhere. I'd hoped for the school's sake he was on the track team because he got out of there in record time.

Fast forward to March. I get great grades. My profs like me. I made a few good friends in the dorm, and one of them and I plan to rent an apartment together next year. My social life still sucks though. I've had an actual 5 dates. 4 with guys, one with a guy who confessed he was gay, but was getting tired of being hassled. Does wonders for a girl's ego, being used as a beard. However, that date helped me out because Lucas introduced me to Ron, his boyfriend. Oh no, I'm not hot enough to turn a guy, believe me, but Ron was a pretty sweet guy who decided that I needed a makeover. He took me in hand and set out to transform me. I explained that I was on a pretty tight budget, but he would have none of it.

"You, are a beautiful woman inside, and it would be a personal pleasure to help you out! The hair and makeup would be free as I run my own salon, and I can get you deals on everything else! Place yourself in my hands! Allow the inner beauty to shine!"

Next saturday morning, he whisked me off for a day of "uncovering true beauty" as he called it. First stop was his salon, and two tons of glop hit my face while my finger and toenails were done for the first ever time by a pro. The glop came off, and he went to work with color and cut. An hour later, I didn't have the big hair that was currently so popular, I had what would be known as the Rachel cut in a few years. I didn't know it then, but I was ahead of my time! It looked great! Makeup was next, and I was revealed as...being kind of pretty? I'd never known or seen it in myself. Then he whisked me off to a popular store, and I got several nice things, and two pairs of shoes for next to nothing from a very nice man, who Ron explained, owed him big for introducing him to the love of his life.

I had to learn how to walk in the new shoes (they had higher heels than I'd ever had), but I got all dressed up for the night and we were going to a popular club, and my best friend Lisa promises me I'll turn a few heads. When going out I've noticed I don't get asked to dance until about an hour after we get there, when the guys have all had more than a few drinks and decide I'm not that hideous. She gets asked within seconds, usually. You wouldn't believe how many nights I've had the dorm all to myself that way...

We walk in, it's not too crowded, and grab a table where several other friends join us. Yep, the six foot five hunk grabs Lisa as soon as she sits down. Callie goes less than a minute later to a really hunky Asian guy, and....

"Excuse me, would you like to dance?

I turn and sure that he's asking Claire I ignore him him until he repeats himself.

"Maybe you're deaf, but would you like to dance??" He says it a bit louder, but with a grin.

"Me?" I stammer. "You w-w-want to d-d-dance with me?"

"Sure, you're...pretty damn cute!"

Cute. Not beautiful. Cute. I'll take it. We dance, several songs and he's smiling and very nice, not grabbing at me, just being cool. After four songs he says he needs another drink and asks what I'm having.

"Diet Coke."

"Designated driver?" he asks with a smile.

"College freshman. No wristband." Over 21 have to have wristbands to drink here.

"College graduate," he says, "one Diet Coke coming up!"

He returns a few minutes later and introduced himself as.....Walter. With a somber look on his face, no less.

"What's the problem?" I ask.

"My name, it's pretty dorky."

"I don't think so. It's different, Sort of like you."

He smiles and relaxes some. "How am I different?"

"You asked me to dance. I'm not exactly popular. I'm majoring in wallflower studies at UW."

"Must be a lot of dumb guys around then. You're very cute, you have a great smile and well, you have very nice legs. I am a leg man after all."

He smiles a bit shyly at that, but I give him my biggest smile and hike my skirt up just a bit. If he likes my legs, I'll give him a bit more. He laughs out loud at that. We start to talk, we exchange backgrounds, aspirations, dreams, we dance, we get closer and as they finally go to a slow song, he holds me pretty closely. This isn't bad! Callie gives me a thumbs up, Lisa's nowhere in sight, but this guy seems to like me! The music speeds back up, but we're getting to know each other and I'm ok with it. It seems like the evening goes by too quickly.

"Um, looks like they're closing." he says with a rueful look. I see Callie kisses the guy goodbye, so she's going back to the dorm, which is what I need.

"Uh yeah, uh, you, um...." I mumble.

"Do I want to see you again?" he says with a grin. "Yes, I do, would you be free for dinner next weekend?"

"YES!" Whoops, I sort of shout it, but he 's cool with it.

"Then here's my phone number, call me Saturday morning, and we'll figure out me picking you up and all, do you live on campus?"

"I do, here's my phone number, call me...even if you just want to say hello before Saturday?"

He carefully puts it into his wallet and I realize it's good night kiss time, and I have no idea what to do. I don't want to look desperate! He's taller than me and takes my hands in his and leans down and....gently kisses me on the lips. I let out a "mmmm" and he kisses again, and I kiss back. I'm not very good at it, but I hope he gets the message that I enjoyed this kiss. The kissing goes on, and we reluctantly break apart. He tells me he can't wait for Saturday. I tell him I can't either so he says he may just call me earlier.

All the way back to the dorm, I am flying. I call Ron and thank him again, and he's happy for me.

Sunday flies by, and in my weekly chat with Mom, she's happy I met a nice guy. I tell her about Ron's kindness and she thinks he's a great guy, and tells me she's got a surprise for me. I'll see it in a few days. Classes pass in a blur, and mail call brings a check from Mom for two hundred dollars! "Keep up the good grades honey, and try to have some fun!" I enlist Ron, and he helps me select a great dress for my date. He also suggests my soon-to-be trademark of lots of green, including lipstick, but I balk at the lipstick, going with the rest of his suggestions. Walter calls on Thursday night and offers coffee, but I have to study, and Saturday can't come fast enough.

It arrives, and he calls, and we set it up for 7. I am dressed to my very best, waiting. Walter is...somewhat floored by me and compliments me on my outfit, and the rather short dress I have chosen. He also greets me with a nice kiss and I am stunned by this nice guy. Dinner is fun, delicious and informative, and when he mentions that the green dress goes nicely with my eyes, I tell him about Ron's suggestion that I wear green lipstick to go with it. He doesn't laugh or mock it, he simply says...."That'd be...very unique, it'd suit you." I excuse myself for the ladies room because Ron insisted on me bringing the damn stuff, so I'm going to take a chance. I wipe off my dark red, and apply the green, not punk, not just looks...different. I return to the table.

"Damn, you weren't kidding! That looks so cool."

"Really? Does it really? I don't want you to think I'm some idiot."

"If I thought you were an idiot, I wouldn't have asked you out. I think you're pretty intelligent. I think you're pretty pretty." he quips and I giggle at his joke.

"Do you really, Walter?"

"Yep" he says.

After dinner, we go to a club I'd never heard of, and it's a ballroom dancing place. I learned all the steps back in high school, but will most likely have forgotten them, but he says not to worry. We dance and dance and dance, and I realize he's pretty good. He shyly accepts the compliment I offer and we continue, and at the end of the song he kisses me again. This time, I kiss back immediately. We eventually sit down and our chairs are now side by side as we do a fair amount of kissing and before we know it, they close. Damn it all to hell. I was enjoying this!!!

We hold hands on the way back to his car, and we kiss again before we get in, and we REALLY get into kissing in front of the dorm, but it's not time yet. For some reason, he knows this and doesn't pressure me in the slightest. We DO manage to spend about 45 minutes kissing though, before we part, with the promise of dinner and dancing next week again.

The week...FLIES by, and Saturday night finds us enjoying some superb Thai food, with a fair amount of kissing in between bites and so on, we spend 20 minutes outside the car making out, another half hour outside the car near the club making out, and our time on the floor is nearing the edge of PG 13. I am horny as hell, but not ready, nor am I sure he's ready. He's a pretty decent guy in this case, but I need to make sure.

"You want to go back to your place and get naked?" They didn't check ID's and I just had to have champagne.

He looks surprised and shakes his head. Oh no, he thinks I'm horrible, hideous, disgusting, he's gay, he would prefer guys to me, he'd prefer to jerk off rather than sleep with me, ohshit ohshit ohshit.

My inner monologue of self destruction is brought up short by his voice.

"I'll bet it's the champagne talking. I don't think you're ready, and I'm not myself."

"You're....not? Is it because you think I'm ugly?"

He frowns. "No, I do not think you ugly, I think you're....gorgeous. Don't put yourself down that way. I've been around though, and I'm willing to bet you ARE a little drunk, and might not be entirely ready yet. I have no desire to push the issue and maybe wreck something good before it gets going just to get laid. What kind of asshole does that?"

"You're not an asshole. You're really nice. But I....thought...."

"That I'd dive into bed with you?"

"um. Yeah."

"What's your rush pretty girl?" He's smiling again.

"I, um, well, I'm a, you"

He laughs at that. "You in such a tearing hurry to get rid of that? I think I like you. A lot. I think you like me. A lot. It'll happen, but do we need to force the issue? Let's enjoy some nice time together and let it take it's course?"

He kisses me again. Deeply.

"Besides, if you enjoy this, just imagine what else can happen later?"

Oh...I can. Believe me, I can. We have fun dancing, and we make out some more. I switch back to Diet Coke and sober up enough to realize that he's an incredible guy. Most guys would have dragged me to the closest bed and had their way with me. Not Walter. He's....a gentleman.

Two more dates pass, and we have lunch together twice a week, and in the light of day, and stone cold sobriety I tell him.

"Can next Saturday night be THE night?"

He takes my hand. "You sure?" I nod in the affirmative.

"Yes, but I'm going to cook you dinner. THAT, involves some serious work."

I offer to help. "I can get whatever you need at the store!"

"Not that kind of work silly. I need to clean my place up. It's guy-level clean, but not nice enough for you. Can I bail on the movies tonight to get it in shape?"

Hmmm. I really wanted to see that new Demi Moore movie, but I'll forgo the pleasure. I let him off the hook with his promise to have lunch with me three times next week, and off he goes. Saturday night is sooooooo far away.

It's not all that bad of a wait, even if I did masturbate quite a bit. I've also asked Lisa for all the advice she can give, which she willingly gives, and for a ride to the mall so I can get something nice to wear. For...after dinner.

Saturday evening comes, and despite it being at his place, I'm dressed to the nines in a dress borrowed from Claire, with my sexy nightgown packed in my bag discretely. I also have condoms because I may be new, I'm not stupid. We didn't discuss safe sex, but I'm sure he's ok with it. He's got a very nice suit on, and his place is spotless. A friend of his was supervising the kitchen while he picked me up and he takes off with big thumbs up to Walter.

"Your place is beautiful! So spacious. You could fit six dorm rooms in here!" I joke, but it's true, his apartment is not far from Lake Washington, and it has a dazzling view, plus tons of square footage.

"Thanks, I can't believe I got it at such a good deal. The guy who owns the building was renovating and ran out of cash. I told him I'd take it, despite it being unfinished, and even help with the work in exchange for a better deal on it. He offered it to me at 60% of what he would have asked, and I offered to take a three year lease at that rate, and he took it. With my help, it was done in three weeks, and I have a great place at bargain basement prices."

"So you're....good with your hands?" I ask with a coy smile.

"Very." He's holding a remote and he pushes a button and sound flows out of hidden speakers. It's Fred Astaire and "Cheek to Cheek". We'd danced to a different version of it two weeks before, but this is the original, the one I fell in love with as a little girl watching old movies on Saturday nights with Mom. He tosses the remote to the couch and takes me in his arms. It IS heaven, and not only am I planning on having sex with the guy, I think I'm seriously falling in love with him. Woohoo! We dance to several slow romantic ones, and we kiss and he bows to me.

"As much as I'd love to keep it up, my kitchen calls to me, I had a twenty minute window!" he says with a grin. "Let the tunes continue, albeit at a lower volume." He grabs the remote and makes the adjustment.

Dinner is incredible. I compliment him on his skills and he explains that due to a broken leg he had to skip the two classes he needed to graduate. He was able to catch them up in summer sessions, but with a four hour window between them, he was bored and took an offered cooking class that was close enough on the campus that it was still convenient.

"I graduated in September for my degree in engineering, but stayed in school at nights to take three more cooking classes. I guess I have a flair for it."

He did. Duck L'orange is NOT an easy dish, but it tasted as good as it did in Paris when we went there for a family vacation. So did everything else. He confessed to running short on time, and buying the tirimisu at a local restaurant, but we never finished it. Somehow, we decided that we'd make a delicious dessert of the other.

We start by kissing and without words, we slowly drift to the bedroom, we slip into it and as the door slowly shuts behind us, his hands begin to flow as he softly squeezes my butt with one hand, while the other caresses my breasts. I let out a sigh of pleasure and his smile lights up. I realize that my purse and my sexy nightgown are still in the kitchen, but my body seems to not be paying attention to anything but his body. His jacket flies off as well as his shoes, and mine tumble to the floor, as we sink onto his bed. I have never been this close with a man, and my heart starts to beat faster as I feel very warm, but not the least bit scared. I'm excited, but him, I know he will be the kind of man I've always wanted for this.

He gently kisses me as his arms encircle me, and I feel very safe, and very happy, but I realize that I have to be smart. My purse, and the nightgown are indeed in the kitchen, but so are the condoms! How do I tell him we need them? We keep kissing and I start unbuttoning his shirt, and the straps on my dress slide off at the same time. He gently reaches around me and his nimble fingers unzip me. Moment of truth here, if he realizes the bra is padded he might laugh! Please no, anything but that! No laughter, but a knowing grin as he gently unsnaps it, and my less than gigantic breasts are there for him to ogle, if he's willing to ogle them, that is.

"Very, very nice..." he mutters as he leans down to gently kiss my nipples. It feels like electric fire as he does, and I feel so good, but now the panic sets in as I don't know what I should be doing!!! Think, you ditz, think! You're getting incredible grades, you SHOULD be able to figure this out! Auugh! Panic mode worsens! Condoms still in kitchen! Is he just going to shove it in? What do I do? What will he think if I stop him? Will he get mad? Laugh at me? Then I open my eyes to realize he's stopped kissing me, but he has a puzzled look on his face.

"What's wrong?" he asks in a gentle voice. "You look kind of, I dunno, flustered?"

I go bright red at that, but damn it, he's right.

"Um, you're going to think I am the biggest dork out there."

"Nope, not gonna happen." he says with his charming smile.

"Uh, I really, er, don't know what to do here. I love what you're doing, but am I supposed to be doing something to you? Or just enjoy what you're doing? Have I told you I'm a virgin?"

That sounds pretty lame, even to my own ears.

He softly chuckles. "Yes, that fact did come up at one point. I never thought to realize that you're new and really can't be expected to know a lot of this stuff. You do kiss really, really well though."

"That's sweet, but like I said, I'm not even sure where to start with you. And there's another problem."

"Which is?"

"We never discussed safe sex, but I've got condoms in my purse. I think you're great, but we're going to use them, I don't need to get pregnant or a disease. Not that I think you have one, of course!"

This is going horribly and I'm horribly embarrassed, but he continues to softly laugh, but it builds and now he's laughing like he does at a great joke. I am about to start crying. This is...miserable.

He stops laughing, and puts up his hands. "I am so sorry to laugh, but it is kind of funny. From my side of things."

Now I'm a little defensive. "What's so funny?"

"You are so nervous! You don't need to be. I'm not exactly the world's greatest lover myself, and I'll admit to being a bit nervous myself! In case it's escaped your notice, I like you quite a bit. I really want this to go smoothly, but good stuff is never easy, is it? I have condoms here, or if you want, we'll use yours. I have no intentions of asking you to have sex without them, I'm fairly smart, too. I don't want to be a father yet, nor do I want a disease, not that I think YOU have one, either!" and he giggles as he says the last, and I join in. Our sheepish grins cause another round of giggles as I get up.

"Well, Walter, I do feel comfortable with mine, but there's something else I wanted you to see. Let me go get my purse."

"But of course!" he says with a laugh.

I run into the kitchen and grab my purse, and I duck into his bathroom to change. He's enjoyed undressing me so far, but this thing should get his attention! I settle it into place, and a quick mirror check shows that I don't look bad at all in it. I slowly walk back into the bedroom and I'm rewarded by a sharp intake of breath by Walter. I blush, but I twirl to show it off and his wolf whistle tells me he likes it.

"You are very beautiful." I look to see if he's joking but his face is total sincerity. I blush even more!

He slips his pants off, and his boxers are baggy, but his erection is fairly obvious and I can't help staring at it. An idea comes to me and I pull the bottom of my nightgown up to reveal my trimmed bush which Lisa insisted I do, and he looks with a smile.

"OK, handsome, I showed you mine, now you show me yours!" He slips the boxers off It looks huge, and it's obviously rock hard. I lie down on the bed next to him and we reach for each other at the same time and our lips meet again.

We kiss and I try to show him how hot I am for him, and he responds the same. We roll over and I'm on my back as he begins to kiss my neck, and then he works his way over to my breasts and sweetly kisses my nipples.

"Now just let me show you how I like to make you feel good...." He does as each kiss gets me hotter, and he circles my nipples, sucks on them, and gently bites them with his lips. God this feels good as I just caress his shoulders and back, and his skin is softer than I thought it might be. His kisses now move south and he gently pushes my legs apart and I pull my knees up to give him some more room.

"You are soooo sexy, baby..." he says softly, and then he sets his lips to my pussy lips and his tongue parts them as he tastes me like no one ever has before. Now I know why all my girlfriends love men who will go down on them, this is fucking amazing, he's softly licking me and I'm almost to orgasm! He changes up and licks deeper, and his fingers part the lips as he begins to flick his tongue on my clit. I can't help myself as I let out a little yelp.

"Ooohhh that feels incredible, you keep up with that!"

He does as he sucks it, licks it, and slows up to lick me as deeply as he can, and I begin to cool off, but he's teasing me, as he goes back to my clit and I get all worked up again, and this time, I'm moaning loudly as he works his magic on me. His hands glide up and caress my breasts, and I take one of them and suck on his middle finger which elicits a grunt of satisfaction from him. Now he ever so gently bites down on my engorged clit and sucks it as hard as he can and I come with a yowl!

"Oooooooh!!!!" And he doesn't stop! He keeps licking and sucking and I suddenly appreciate women's ability to have multiple orgasms as I come again, and I can't really control myself as I pull his head into me, and hold him tight until my orgasm subsides! I just lay there holding him for a few moments and I let him go with a sigh as I come down from my sexual high. He lifts his face to me, and flicks his tongue again and I giggle because it's silly, but damn, it's as sexy as can be!

"How was that, baby?"

"Oh god, it felt so good, you made me feel that made me come twice!"

He smiles as he comes up and wraps his arms around me.

"What? No kisses for me?" I ask.

"Well, some women are a little bit turned off by kissing a guy after he's gone down on her. I didn't want to pre-"

He's cut off by my lips as I kiss him deeply.

"I'm not some women, you made me feel like I've never felt, kiss me all you want!"

He laughs as we keep up with the kissing but I reach my hand down and carefully touch his cock. It is as hard as a rock, and I softly hold it, not sure what to do with it, so I just rub it softly and I realize he's a little wet himself. He realizes it and starts to apologize but I cut him off.

"No, it's part of you, and I need to get used to it, so no worries, okay?"

I continue to rub him, using the incredibly tiny amount of experience I have to guide me, and he looks as if he's enjoying it. However, I have no experience at all in anything else, so I take a deep breath and slowly put my mouth over the head of his cock. It sort of fills my mouth, but I slowly try to take more of it in, although I don't get very far as my gag reflex kicks in. I look up expecting to see disappointment from him over it, but he still smiles at me. I try again and I get more of it, and only gag a little, so I lick it as I start to go up and down on it. It's okay gor a moment or so, but then I go too deep and gag again and I have to pull away.

"I'm so sorry honey, I...can't do that very well."

"'s ok, just kiss me and we'll cuddle for a bit.."

We do that, and he's still very hard, so I tell him I want him inside of me. He kisses me passionately, and grabs a condom. He tears the package and it's sort of a red color, but he carefully wipes himself and rolls it on. It's the moment of truth here, and I am so nervous, but he's promised he'll be gentle, and I know he will be. I spread my legs and he carefully positions himself and slips it in, but doesn't get far before my hymen stops him. I know this might hurt a bit, so I tense up, but he just kisses me softly and I relax. He tries again, and now I know he's going to have to thrust pretty hard to break my hymen so I softly tell him to go for it. We kiss as he pulls back and thrusts very hard and I feel my first cock slam into me, and I just hold him tight. It hurts, a lot and there are tears in my eyes and I don't want him to see them! He makes soft soothing noises as we hold each other tight and then after a few moments he slides it back out a bout and inch or two and ever so gently slides it back in and holds me close. I'm still stinging a bit, but I realize that's only from my hymen breaking, and the feel of his cock inside me feels....very, very nice. I whisper for him to go easy and he does as he starts to gently fuck me. He leans back to look in my face and I see concern that I might still be hurting. He is so sweet!

"It's all right, just go easy for a bit, I like the way it feels..."

He lets out a sigh of relief and continues with his gentle stroking and he goes a little deeper with each thrust. The sting is gone now, and I'm starting to feel very good.

"Can you go a little bit harder? Maybe a little faster?" I whisper. He answers with a chuckle and he picks up the pace. He goes as deep as he can now, and my pussy feels full, but it's a warm and wonderful feeling! He fucks me for a few minutes and then he holds me as we roll over and I'm on top!

"See how you like being in charge of it!" he says with a smile.

I gently ride him and I realize being in control is very...empowering. I try different angles, harder and softer thrusts and I arrive at a nice pace that makes me feel good and after a few seconds of that, I realize he's thrusting as well! We go like that for another minute and without warning, I erupt into an orgasm and I yell it out!

"OOOOOH!! AAAAHHH!!!" He's not bothered in the slightest as he flips us back over and he starts to really fuck me hard! He doesn't last that long as he starts making grunting noises and then he slams into me very hard and holds me tight as he lets out a loud, almost growl as I realize he's coming in me just as my second orgasm lets loose! We both gasp as we ride out the pleasure, and then we slowly pull apart as he carefully holds the condom. We're both to winded to say anything as we just breathe deeply. We're on our backs and as we eventually come down from our pleasure, he props himself up on his elbow and smiles at me.

" were amazing."

"Me?" I splutter. "I just kind of was...along for the ride!"

He shakes his head. "Yeah, right. Like you didn't ride me like a pogo stick when you were on top? That felt so good I was afraid I was going to come right there!"

"Really?" I ask.

"Really! You had two I think, girls are so lucky there."

I smirk at that. "Well, we deserve something for having to put up with you men. You think you can just be sweet and kind and sexy and cook me a great meal and....make me love my first time and all that, well yeah, we should get multiple orgasms!"

"I am glad you enjoyed it, you were very tight there, but I'm glad we got that all worked out. You might be a little sore for a bit though. Sorry about that."

"No need to feel sorry, sexy. I knew it might hurt the first time, but Lisa told me that going for another round as quick as possible makes it feel better."

He laughed. "Well, we wouldn't want to ignore her advice, would we?"

As we began kissing again, I knew that this man was so very special and he always would be because he was my first. It lasted until my sophomore year, but it was an amicable parting. I used his real name, so Walter, if you're out there, I still think about you and that special night from time to time. Thank you again.

This is another one from the true stories file, I had issues writing it, but it's all okay now. I guess growing up helps!