First Blowjob Courtesy Of Annie

Thank you to TheSometimesGoddess for editing.

This is the account of my first blow job. The names have been changed and I've had to make some small embellishments to fill in the gaps in my memory. The over all sequence of events and about 90% of the dialogue actually happened. This is essentially my first attempt at erotica and writing in general. I started this story a few years ago, and recently found it floating around on my hard drive. I intended to make a trilogy describing my sexual awakening. I'm still undecided on whether or not I should write the other two, or just leave this be.

*

It was January and towards the end of my 22nd year of life; I was incredibly frustrated and had been down on my luck dating wise for the longest time. It had been almost 3 years since I had a serious relationship, or really even just fooled around with anyone beyond some clothed dry humping.. In fact, I hadn't had an orgasm from someone else in over a year. I was talking with a few girls towards the end of the year before, but most of them fell through, got boyfriends, or lost interest. I wasn't horribly ugly; in fact I got compliments all the time on my smile and my eyes. Because I genuinely cared, I usually ended up more of a big brother figure, as opposed to the kind of guy that girls want to have buried balls deep inside of them.

However, one night I'd gotten an IM from a girl who I had been talking to the year prior. She was 19, nice rack. She was also one of those girls who dyed her hair all the time.. I hadn't really thought of her as anything more than just another girl until I thought she was interested. At the time it had sounded like we were going to make out some, but as my shitty luck would have it, she wound up in a car accident by some drunk driver. After that, she was hard to get in touch with in general because she was recovering from her injuries and kept a busy schedule. A few months later, I was off work one night, bumming around the house in a T and some PJ pants, relaxing and enjoying the night off when all of a sudden...

Annie: What ya up to tonight?

Me: Not much. Yourself?

Annie: Nothing, you wanna hang out?

Me: Sure if you want. You able to drive again?

Annie: Yea

Me: That's cool, I'd like to

Annie: I'm free all night, so seven?

Me: That works, still have my number?

Annie: Yes, I do, what do you wanna do?

Me: I dunno don't have much to do, watch a movie I guess

Annie: Is there any way I could bug you for a massage?

Me: Hells yeah :D

Annie: Ok, thanks a ton, you're awesome

Me: No problem, so what you been up to? Feeling better?

Annie: I actually just got done riding (she liked to 4wheel)

Me: Yay :)

Annie: Still a little sore

Me: Riding eh? grr lol

Annie: Oh baby, don't growl. Lol, just messing

Me: That's too bad ;)

Annie: I'm getting ready to leave. How do I get there?

I told her how to get to my house, and took a quick shower. Eventually she showed up, not dressed in anything fancy, just windbreaker pants and a button down long sleeve top with her sleeves rolled up. I had forgotten she was rather short (about 5'2), and hadn't seen her in several months It was short and dirty blondish with some red highlights that complimented her figure and big brown eyes nicely. Correction, the eyeliner brought out her big brown eyes out perfectly!

"Hey Ann, glad you found it, it's fairly easy to find...love the hair." I told her nervously.

"Thanks, I just dyed it... It wasn't too hard to get here."

We walked back to my bedroom after a few min of idle chit chat, my living room TV was on the blink. I pulled out my binder of movies and presented it to her.

After a few minutes she picked out Muppet Treasure Island, one of my favorites. Hey now, I may be an adult but I love me some Muppets! I put the DVD in as she sat down on my bed. After setting up I sat next to her, not incredibly close though.

About half an hour into the movie I heard, "Hey Matt, would you mind giving me that massage I asked for, my back has been killing me!" "No problem," I said, as she rolled over onto her belly.

I started rubbing her shoulders, squeezing the tops by her neck. Her shoulders felt very tight so I started a little more gently, gradually building pressure till she was more relaxed. I worked my way down along her back when she said she felt like she needed to have her back cracked but she had been unable to do it herself and no one she asked could do it either.

"You'll have to lay down on the floor first though, trust me," I said. We took a blanket from the bed and laid it on the floor. She started to unbutton her top and laid it on a chair, but still left her bra on, exposing her nicely firm tummy before she laid down on it. I started to straddle her butt, so I could have better leverage. I put both hands on each side of her spine towards the small of her back.

"I want you to breathe in all the way, and exhale all the way, when you're done ill push okay?"

"Alright," she said.

I could feel her back raising as she inhaled, filling her lungs. She started to exhale and when her lungs were empty I pushed upward, elongating her vertebrae. I could hear a slight crackling along her spine as she slightly moaned. To be honest I'd started to get a hard on. This lovely young girl was laying down with me essentially straddling her ass; I was almost positive she could feel me grow in my pants after I heard her moan.

"Feel good?"

"Oh yeah..."

"Alright then, I'll continue."

I placed my hands a little farther up her back, "You'll want to inhale deeply again," she did, and after she exhaled I pressed again. Like before her back cracked a little and just as it had happened before she gasped slightly before a relaxed "mmmm" escaped her mouth.

I slowly worked my way up her back, till I got to her shoulders and stopped. By this time I know I had an erection and I'd bet money she had felt it pressing against her ass. I'm not exactly a porn star, but I am just under 8 inches.

"That was amazing...I haven't been able to crack my back since before the accident!"

"Well, I do aim to please."

Only a few minutes had gone by during this time I had been massaging her. She offered me a back rub as well, and of course I accepted. I took my shirt off and we switched places, although it was somewhat uncomfortable lying on my stomach with a throbbing erection. After a short while it subsided and I was in heaven as she worked along my back, using more skill than I possessed. I only knew a few tricks, particularly the one I used on her back, but this was lovely. She even caused little moans to escape from my mouth; I had almost fallen asleep before she was done.

She climbed off of me and started to put her shirt back on as I got up off the floor and put my t shirt back on. We sat back on my bed, her first followed by myself. I turned down the lights, and shortly afterward I had put my arm around her, holding her closer as we continued to watch the Muppets and their silly antics.

Before too long I had gained up the courage to utter some words, "So how're you feeling? Comfortable?" I asked while looking into her eyes.

"Yes, very..." as she smiled.

"Would you like to be more comfortable?" I asked with a slight smirk.

"Sure..." she responded with her eyes twinkling with mischief.

I leaned in gently to kiss her...our lips softly touching each other, as my hand came up to her cheek. My mouth slowly opened, and her mouth followed in return. I slid my tongue across her lower lip and her tongue came out to meet mine, caressing it softly.

Her hand reached around and started rubbing my side as the kissing got more intense. Her tongue was just as active as mine, her touches matched mine...something I had rarely seen in a girl. It continued on till I was nibbling on her neck and she began to stroke my thigh. A few minutes of tasting her neck had passed before I moved onto sucking on her ears. By this time she was pulling me down beside her and I was caressing her tummy up and down, working my way higher till I could rub my hands across her perfectly sized tits.

"You're a really good kisser, Matt," she said, before moving to my ear and nibbling it, letting me hear all the moist noises her mouth made.

"Thanks, although I'm kind of rusty...you are amazing yourself!"

I inched my hand closer to the buttons of her shirt while feeling her soft lips on my ear and neck, and her hands across my sides.

The buttons came undone in no time, and she hadn't resisted, in fact helping me with the last few. Eventually she took the rest of her shirt off and I went to kissing her bare collarbone and my hands immediately went to her tummy caressing her navel. With the moan that came from her mouth, if I wasn't raging hard I don't know how I wouldn't be...working up more courage I asked if she would be more comfortable with her bra off...she nodded and replied with a soft "oh yeah," the dim light making her dark eyes even darker. "But only if you take your shirt off too," she added.

In my day I had learned to unclasp a bra with one hand...I was hoping this trick would not fail me now, when I seriously needed some boobage. I went back to kissing her, sliding my tongue across her lips, she suddenly began to suck my tongue into her mouth and my mind went totally blank for a moment. Eventually, I remembered what I was doing and found the clasp with my right hand, dug my index finger down pulled, and then pushed with my thumb, loosening the hooks that held her perky tits captive.

She began to slide my shirt off over my head and she immediately started rubbing my bare chest, her hands felt so warm. I felt so manly with her small hands touching me; I took over and rolled her onto her back, climbing between her legs...looking down at her like a hungry wolf, eyes full of lust. I leaned down to kiss her again, forcing my tongue into her mouth only to be greeted by more sucking. Immediately I ground my hips down against her hips, probably bumping her clitoris with my pubic bone...all between my pj pants and her windbreakers. Her reply was to continue sucking my tongue harder into her mouth.

I could see her tits bounce as I thrust against her, nipples erect... "What cup size are you? It's been a while and I'm horrible with sizes."

"They're Cs...one of your hands full." She took my hand and placed it on her breast and I instinctively groped at it. I leaned down and kissed the other breast, with my forearm supporting me, my weight across her pubic bone rocking slowly. I could feel my cock press against where her pussy was, damned clothing! I began to trace my tongue around her nipple, but making sure to make no contact with it, before making tight circles on it with my tongue.

My free hand decided to pinch her other nipple, while I began to rock back and forth more. She wrapped her legs around my hips. Shortly after this increase I heard her starting to pant, "Oh Matt, yes...yes...mmmm." She dug her nails into my back while she moaned softly.

My thrusting subsided, still ragingly hard in my pants. "Did you actually come?!"

"Yes, just a small one, but I came," she answered.

"Oh wow, it has been years since I've gotten a girl off!" I said, a little shocked.

"Really? I couldn't tell...but now it's your turn."

Fucking awesome...

She started to kiss me again and pulled me closer, I rolled onto my back and she straddled right above my throbbing cock and started to rock. Her bare tits were visible due to the dim light mainly coming from the hall, and the TV playing the menu to the movie illuminating my eyesight. I could feel my cock rub the inside of my boxers, the foreskin sliding as she moved up and down across my lap, feeling like I was actually inside something.

She lent down and started to suck on my shoulder, starting to leave a hickey as I groped her ass with both of my hands, guiding her pace and pressure. It felt so good, but I felt so far away from coming, yet I wanted to explode in my pants. She took one of my hands and slipped my index finger between her lips, sucking it into her mouth, rubbing her tongue against my fingertip. So I picked up the pace a bit and thrust up against her hot crotch, rocking her hips while her hands squeezed at my bare sides.

A few minutes of this grinding and I was getting frustrated. I couldn't come, yet in the past I had been able to with my exes. If we had been actually having sex, she would have been fucking my brains out; no doubt I wouldn't have a problem coming inside of her pussy. Especially the way she sucked my tongue when we kissed. I didn't want to be a virgin forever. But it was no use, my ass was beginning to cramp, I knew I wasn't going to come from this...shit.

"Can you lay down beside me? I'm getting tired, and cramped."

"Sure.. did you come?" She asked as she lifted a leg over me and laid down. Her hand started to caress my tummy. My weakness!

"No, I don't know what it is. You're hot and I'm horny as hell..."

"Don't worry, I can get you off," she said as she continued to rub me.

"You don't have to, its fine. You've done so much and I'm having fun. It's just not working."

"Well, how do you feel about a blow job?" she asked immediately looking so innocent.

I was dumbfounded...my head was screaming out,

YES! YES! Is this actually happening? A girl offering to suck me off?!

"Wow, uh I dunno. I've never really had one before... I mean my ex did, but only for like a few seconds before we got interrupted by her mother walking down the hall."

"That sucks..."

"No, it doesn't...that's the problem."

We shared a good laugh at my expense before she climbed back on top of me, straddling, but instead closer to my feet. I could feel her hands trail down my stomach to my waist. She pulled down my pants and boxers down together, setting me free.

"Wow..." she said with a bit of pleasant shock as she caressed my length.

I thought,

Nice...she is impressed. This is going to be awesome!

I was almost 8 inches, fairly thick for that length, and I had a slight curve downward; certainly unique I've been told. I started to kick the rest of my pants down off my legs while she got into place.

She slid my foreskin back slowly and licked the tip of my head with the tip of her tongue, then a little more with more of her tongue. She started to stroke me off with one hand and touch my balls with another. It felt so good I sort of giggled, since it tickled some and before I knew it she wrapped her warm, moist lips around my fat head and was sucking gently.

"Mmmmmhhh..." was all I could do or say.

Annie stopped briefly, looked up smiling and asked, "Are you comfortable?" before placing her lips back on my cock and started stroking again.

"Fuck yeah!" I managed to say. Then, for some reason I said, "You know, you don't have to if you don't want to." Stupid nice guy shit slipping out...trying to ruin my first blow job!

She took her mouth off of me but continued to stroke, "I don't mind at all, you helped me, now I'm helping you!"

"Do you mind that I'm not circumcised?"

"Nope, I don't have a problem with it."

Her strokes lengthened till her hand was at the base of my cock, all the way till she made the skin cover the head and back down again while her lips barely touched my head.. I felt like I was in heaven or something, if heaven was anything like having a girl like this suck you off. My hands found their way to her hair, which the light was so dim I couldn't make out the highlights, but I could feel how soft it was despite being dyed. I started to caress her ears as she began to start sucking harder, up and down my pole. This is what I had been missing all these years.

She swirled her tongue around my head while her non jerking hand was squeezing my balls gently. My mind was a wave of sensations, all coming from one area...her tongue felt like an angel's wing (or some poetic metaphor) as it moved up and down against the underside of my head. I could feel myself getting closer and I think she could feel my nuts tightening. If not, I'm sure she could taste more of the precum that had undoubtedly been leaking out since she first climbed on top of me. Was this real? Was I dreaming? Is this what actually happens to other, lucky people?!

I was looking around the room with these thoughts of ecstasy, when I saw some tissues by the bed stand used many times for late night masturbating thinking of hypothetical situations, in which the same things that were happening now would take place! Nothing compared to this, mind you, but being the gentleman I am I thought she may not want to swallow, so it might be a good idea to ask. The last thing I want is this girl who's giving me the pleasures of her mouth to start choking and yell at me.

"So...how...how do you feel about swallowing?"

She gripped my cock tightly with such a little hand, "Don't worry, I swallow."

SCORE!! I could now relax, I was in good hands...and mouth.

Annie released her grip, slid my skin all the way back, and slowly tried to take me as deep as she could in her throat. She got about half way in before she started to tense and gag a little. She slid me back out of her mouth and stroked just the head with the skin down.

"Guess you won't fit down my throat," she said with a chuckle, twisting her hand on my exposed and well lubricated knob. The twist of her fist around my head was getting to me. I was beginning to think that I might squirt all over her hand. However, she slid her hand downward, and began to stroke me again while her lips again caressed my tip, moving their way down to the rim of my head, sucking it while she stroked.

My legs started to shake, my breathing got even heavier. It felt like my lungs were going to come out of my cock instead of jizz. Obviously she knew what was happening and she began to caress her tongue back and forth under my head while she stroked my length. That was all I needed. My body tensed, I almost sat up and gripped her shoulders as I moaned...squirting what felt like every drop I had in me. She slightly gagged, probably from my come hitting her in the back of her throat, but still she continued to swallow me down with slurping noises from my soaked cock. The hand that wasn't stroking me went back to squeezing my sack.

Eventually all good things have to end. I was getting too sensitive to stay in her mouth, and she slid me out. The cool air felt so wonderful against my slick, and rapidly softening cock. I was still trying to catch my breath, in that familiar way after a climax. My thoroughly satisfied cock started to lay down against my stomach.

"How was that?" she said, wiping her lip with the side of her fingers.

"That...ohh...mmm. That was fantastic. I'm still trying to catch...my breath."

She began to straddle me again, and laid down on top of me. I can still remember years later, the feeling of her warm tummy pressed against my slippery cock, probably leaving a little ooze of cum by her navel. She kissed me softly on the lips and mussed my hair a little.

"It's okay, you can kiss me for real, I don't mind my taste. I'd gotten curious when I was 17 and tasted it." She smiled and chuckled again, shaking her head.

She leaned in and caressed my cheek as her tongue slipped between my lips and sought mine out. It was oddly cool to the touch and very salty tasting. I must have come all over her tongue. I began to suck on it hesitantly, tasting myself and rubbing her bare, warm back with my somewhat shaking hands.

We talked for about 10 minutes about random things, exes, past experiences, etc... I offered to go down on her but she said she was already late getting home and had to leave. She had fun as it was. I walked her to my door after we got dressed, I kissed her goodbye and wished her a safe trip home.