Deflowering Lessons

Warning: cuckold fantasy.

Hi, my name is Zack, and this is my story.

I few years back I was on my last weeks of high school, and I had been two years together with my girlfriend Cindy. She was a pretty hot girl and also somewhat flirty and playful. I was very lucky that we both fell in love quickly and innocently as teenagers do, since I was a shy and cautious boy, without much seduction skills.

My best and oldest friend was called Jeff. He was an athletic black guy with whom I played since we were kids. When we hit puberty, he got taller and stronger than me. He started going out with girls, which I was too shy to approach, so our lifestyles started diverging a bit, but still we managed to hang out a lot.

One day we were changing in the school locker room, Jeff was next to me. With his characteristic blunt style, he asked, "So have you popped her cherry or not yet?" He knew from previous conversations that Cindy and I were both virgins.

I didn't have any concrete plans on how to do it, but I tried to sound as manly as possible, "I'm working on it. I think it'll be soon." While saying this, I looked briefly to the side and accidentally saw Jeff's hanging cock. I always tried my best not to look at other guys' dicks or anyone seeing mine. I had started growing pubic hair a couple of years later than my mates, so back when we were in our early teens they all had some manly hair and I didn't. That embarrassed me so I got the habit of being very prude in the locker room. Also, I didn't want to look at other cocks and get accidentally aroused by them. Getting a hard-on in there would be a nightmare.

I'm not gay, I feel disgust at the idea of kissing a guy or having a romantic relationship with one. I find women hot. But something happens to me when I look at an erection. I'm curious how it would feel if I touch it, or even taste it. I feel an awkward admiration for the symbol of masculinity that is a hard penis.

So, I had seen Jeff's dick and it was clearly bigger than mine when flaccid. I wonder what was his size when hard, mine is pretty much average. That night at home I fantasized about this. I imagined we were both erect and touching each other. The contrast in our skin color was kind of hot. Imagine if Jeff knew that I fantasized about touching his cock. I thought this was pretty pathetic of me and perhaps I should be more daring with Cindy, instead of thinking about men.

I few days later Jeff invited us to hang out at his place. His parents had gone out of town for their wedding anniversary, so it was only the three of us. "They're banging each other in some nice hotel," he told us. He received us wearing a new shirt and sneakers. He was always very particular about his style. I, on the other hand, always wore the same plain clothes. We moved to the deck in the backyard, where he grilled us some juicy steaks. We had some cold beer, although it was not much in my custom yet. I was not much of a party-goer, I had drunk alcohol a couple of times before, but never to the point of being completely drunk.

Then we moved inside, to his parent's bedroom, which was actually really large, it had a small living-room where Jeff had left some strong drinks on the table. We started tasting all that stuff with weird names. Cindy found most disgusting, but the effect was still clearly visible on her. When we were all drunk, Jeff suggested we play something. Cindy agreed. I didn't like party games as they make me anxious, but the decision was made. He proposed to play strip poker, the cocky bastard.

I hadn't seen Cindy naked yet, so this didn't sound like a very bad idea. Worst thing that could happen is that I ended up naked in front of my girlfriend and best friend. No big deal. I agreed to play and Jeff went looking for the cards. Cindy said nothing but I noticed she was mentally preparing and was a bit nervous. I tried to calm her, "Don't worry, babe, I'll let you win."

Jeff came back and we played a few rounds. It was a warm summer night so we didn't have too many clothes to start with. Soon Jeff and I were down to our underwear, and Cindy still had a short dress on her. We were sitting in couches using a low living-room table, so there was nothing to hide our bodies. My buddy was in front of me, manspreading and wearing some athletic briefs which clearly showed his bulge. I wonder what my girlfriend thought of our bodies. I was pretty skinny, and Jeff in much better shape. My body language also displayed insecurity, while he was very confident.

The alcohol kept flowing and we were laughing of any stupidity that came about. We played some more poker and it was my girl's turn to take off her dress. It was a white dress with a pattern of cherries printed on it. I had seen her use it a couple of times, and I couldn't help associate it with her virginity. I never asked her about it, but I'm pretty sure she used that dress to flaunt her innocence.

While she was taking it off, her legs and belly already exposed, Jeff gave me a look, pointed at her and made a nod of approval. The cherry dress dropped and Cindy sat meekly, covering her bra with her arm and had her legs crossed.

Next round, again she lost and had to remove her bra. She did it discreetly so we couldn't see her nipples. We were drooling. Then for a third time in a row she lost and had to take off her panties. I suspected Jeff was cheating somehow. She pulled them out with one hand while sitting and covering her breasts. Her pubic hair was visible. She crossed her leg pointing it to my side, so Jeff perhaps could have a glimpse of her pussy, but I couldn't tell.

We were two intoxicated apes staring at her terse teenage curves. Of course, we were getting hard-ons. We made Cindy feel uncomfortable so she fought back, "You two need to play the final round between yourselves." We obeyed and Jeff started to shuffle the cards. I caught him cheating trying to peek at the cards on the deck and called him out. We stood up, drunk and howling. The cards flew around.

In the commotion, my girlfriend clearly noticed the tents we had pitched on our underwear and smiled. I asked her to intervene, "Hey babe, you be the judge. Who won?"

"Both of you lost," she sentenced, still covering her naked body modestly. I guess she wanted to take revenge for having her stripped.

"Fair enough," said Jeff, and immediately pulled down his briefs. His half-erect manhood sprang up and dangled as he stood back up again stoutly. Cindy let go a nervous and playful girly scream at the sight of that one-eyed snake, perhaps the first she was seeing in real life.

She addressed me, "Now you, baby." I hesitated a bit, but I figured that the longer I wait, the more flaccid I would get due to my anxiousness, and I definitely didn't want to display myself soft and small, so I pulled down my underwear. My penis was around 6 inches long, narrow, curved to the side and with full grown pubes. Jeff's was 8 inches, wide, straight and shaved. We were not fully erect but his was evidently more impressive.

Cindy stared at mine for a few seconds, maybe assessing the possibility that this is the thing that she'd have to fuck for the rest of her life. Then she looked at Jeff's and commented under the effects of alcohol, "Well, I guess it's true what they say about black guys. But don't worry, baby, yours is pretty enough." This was at first very humiliating, but the fact that my dick was declared smaller out loud also reduced my anxiety about it, as now it was a matter of fact and we were all fine with it.

Jeff came out in my defense. "You're evil, girl. A man's pride is his prick. Take me for example. I get all sort of compliments from women in bed, and that makes me very confident." He then sat back down on his couch, legs spread, arms stretched out, his penis half-standing like a flag being raised, and asked, "Hey, what do you say we hang out like this?"

I responded a bit shyly from the recent humiliation, "I guess it's fine. Cindy, are you ok?" This was her silent response: she reached for her drink in the table while resting her other arm on the couch, exposing her perky tits completely. This was the first time I saw her nipples. She smiled adventurously, leaned back and made no attempt to cover back up. This pumped up our erections.

Jeff then dropped the V-bomb, "Hey, why haven't you guys had sex yet? What are ya waiting for? I mean, look at you, you're a pair of horny monkeys right now."

I answered, first looking at Cindy and then at Jeff, "Well, we gotta plan something, we cannot just do it like that."

"What do ya mean 'plan'?" he questioned.

This was a bit embarrassing to answer, "I mean, like do some research on techniques and such."

"Research?" he blurted. "Man, servicing your girl is not a science project. It's all very natural. Look, you know how to masturbate a girl?" I shacked my head in ignorance. "You gotta massage the clit..." he started explaining, while making a motion with his hand on his lower belly, simulating like it was a girl's pussy.

Looking at his hand, I couldn't help staring at his cock and balls. The memory of the fantasy I had a few nights ago about masturbating him flashed back. There was no way I could attempt something like that, so I focused back on what he was saying. He continued, "Hey, do you even know where the clit is?" I had some vague idea about how the clit looked, but was not sure, so I hesitated. Jeff instructed, "Cindy, give your man a hand here. Show him his clit."

"Just a quick look, babe," I added.

Cindy spread her legs and used her fingers to spread her pubic hair and show me clearly where the clit was. "Here's your clit, baby," she said and started rubbing it like Jeff had shown.

My girlfriend was naked, with legs spread open, masturbating to me and my best pal. I started masturbating too. After years of going out with her, I never could get her this horny, but this guy just commanded her and she spread her legs.

Jeff seemed pleased, "I told you guys you're a pair of monkeys. Hey, girl, do you know how to give head?"

"A friend told me how to do it," she replied with some confidence.

Jeff continued pushing things further, "Hey, Zack. Let's toss a coin, winner gets to test her skills." This was completely outrageous. But I did not protest immediately. Jeff insisted, "I'll teach you all I know, Zack. Just give me this small chance. She's just too hot, man. You'll get her back in one piece, and still virgin. Now, unless she has any objections."

She was still spreading her legs and having her breasts on display. She stopped masturbating to ponder on the matter. "This is getting wild..." she started. I saw her take a glance at Jeff's cock, now full mast. She threw the ball it me, "Are you feeling lucky, baby?"

This was a chance I've never had with her, maybe I should take it now, I thought. On the other hand, she'll probably be more willing the next time we make out, so I can wait a few days. While I was thinking, Jeff had already taken out a coin. "Heads or tails, man." He was very annoying, he wouldn't let me say anything other than those two options. "Heads or tails, man."

"Tails," I said reluctantly. He tossed. Of course, it was heads. Cindy covered her nose and mouth with her palms, emitting a little scream of embarrassment and excitement.

"I think this is going too far," I protested for the first time.

"Don't be a bad loser, Zack," he joked, yet he still noted my distress. "I'll tell you what we're gonna do. We'll go to the bed (we were in his parents' bedroom), we'll lay there and your beautiful girl will take care of us, one after the other. We both win."

That was not a bad deal, I was going to get my first blowjob after all, and he made it happen. This bastard Jeff always knew how to negotiate with me. He saw signs of acceptance in my face and started moving towards the bed while calling us to follow. I looked at Cindy. She had a mischievous smile and was following him in her birthday suit, which told me she had absolutely no problems with this. So maybe I shouldn't either.

He laid on the middle of the bed, with Cindy and I on each side. I started masturbating to get hard again, as the whole coin toss had unaroused me. He was already rock-hard in anticipation.

My friend's cock was the center of attention. My girl sat next to it in a relaxed pose. She stretched her arm to touch it, approaching it slowly with her open palm, like if it was some magical object. You could see the thing pulsating with his heartbeat. She wrapped her fingers around it, probing the texture and hardness, then began sliding the skin, feeling the shaft contour under her touch.

Nobody made a sound, like we were doing some sort of ritual. She then used her other hand to explore his cockhead with caresses and a little squeeze. She gently grabbed his balls and began playing with them too.

Their skin color contrast was the icing on the cake, and the whole scene looked like an artistic performance.

My girlfriend began to lower her head onto it. She gave his cock a tender kiss on the side of the head, then a second one on the tip. Following a regular pace, she kissed her way down his shaft. Her head was tilted and we made eye contact for a few seconds. I licked my lips as we looked to each other. What did that mean? That I was enjoying watching her, or that I wanted to help her?

She could use some help, but I didn't dare to cross that limit with my best pal. Cindy was now kissing his balls. Was she aware that those things are full of sperm, and that the hard cock she was worshipping could hose her insides with them? As far as I know, she's not on birth control.

My girl moved back to the cockhead, and it looked as if she was salivating, an advice she probably received from her friend. She enveloped the head with her mouth, savored it, then retraced while sucking. Jeff purred, "Mmmm."

She made a second dive, progressing deeper. Her hair started to her in the way. My pal gently gathered her hair in the back of her head. I thought this was too possessive of him, to grab my girl's head while she sucked him. I felt I needed to protect her, so I moved closer, took her hair in my own hands and Jeff receded.

I stroked Cindy's hair, caressed her shoulders and back, all while she still sucked him. I really wanted to make her feel special. I caressed my girlfriend's cheek with his cock still in her mouth. When I did this, she stopped sucking and looked at me with a loving smile, like the way you look into a child and admire their innocence. Just below her face was his glistening chocolate tower, which she grasped two-handedly. The image was so jarring that I started to think my woman was crazy, but maybe that's just what I needed. I smiled back to her.

Jeff noticed our special moment and suggested, "Time to switch?" For a moment I thought he meant that it was my turn to suck him (and if he pushed down that path, I would've done it), but then I remembered that it was my turn to get a blowjob. I got very excited and started to massage my clit (I'm sorry, my dick) and get comfortable.

Cindy sat upright and cleaned herself up a bit. Then like a slutty princess dictated, "I wanna have my pussy licked first."

Jeff retraced his legs, leaving me a free path to her, then extended his arm in her direction, with open palm, signaling me to step in. I approached my girlfriend through the bed, we held hands and she asked me a bit naughty, "Are you having a good time?"

I nodded. How humiliating. She laid back, spread her legs slightly and said, "I'm ready."

I started caressing her thighs, looking at her pubic jungle below. I had no idea how to please a woman down there. "You got any tips?" I asked Jeff.

He sat next to me and started to explain with a hand gesture how to finger her, then he spread her labia, which made me a little anxious of him touching her down there, but he didn't put his fingers inside of her, just told me where to lick, while protruding his tongue in a funny way. Cindy was impatient, "Come on, boys. Who's going first?"

I was not very excited about eating her pussy, so I answered, "You decide." And she did. She lifted her feet in the air and locked them behind Jeff's neck, then dragged him down into her bush like some carnivore plant.

I tried to learn how he licked, but I couldn't really see what he was doing with his mouth, so I moved closer to Cindy and clasped hands with her. I watched my girl's reactions as her pussy was being serviced, which together with the sight of her bare breasts made a beautiful scene. Say what you want, but I think my first sexual experience with Cindy was being quite romantic.

When Jeff sensed she was all wet and horny, he backed off and proclaimed, "She's ready, bro."

"You mean I can put it in?" I asked eagerly.

"Not just like that, man," he advised. "You gotta start real slow to open her up. Specially if it's her first time. She's real tight."

I stood there looking at her pussy with a face that clearly showed my ignorance in all of this. Jeff continued, "Look, you gotta press softly and don't force it." As he said this, he rubbed the tip of his cock against my girlfriend's virgin pussy, spreading pre-cum along her labia like it was butter. "See?"

I found this very arousing, but I didn't have a good view so I moved a bit closer, leaning my head to get a better sight. Cindy noticed me so she tried to help me by lowering one of her bent legs to the side. Unfortunately, this also made her pussy more accessible. I don't know if Jeff took advantage of the moment or it was accidental, but his hard cock penetrated Cindy's pussy a couple of inches deep. "Oh ho ho," sang Jeff playfully, either surprised or feigning it.

"Oh fuck," she gasped, shocked and paralyzed.

I moved clumsily towards them, dick in hand, and stopped short not knowing what to do. I looked as if I was going to fuck her but arrived too late. Jeff luckily broke the awkwardness of the moment. "I'm sorry, bro, I got carried away. You wanna go in?" His hard dick was still partially inside her, not moving. I was still stroking mine slowly.

I stammered, "I... I..." I was so incredibly embarrassed and aroused at the same time. My heart was racing. The next moment defined my sex life.

"Just keep going for now," I replied. I really felt more comfortable watching.

"Ok, you let me know," said Jeff.

Cindy looked at me, surprised. The look on her face expressed something like "I'm fucking your friend, are you really ok with this?" I blew a kiss to her to make her feel reassured, while also playing with my cock to remind her we were all just having fun.

She focused back on Jeff who was resuming his slow thrusts. She smiled but still looked nervous for my unwillingness to continue the job. My buddy noticed her and said, "Let me show you guys another position."

He flipped her like a toy and put her naked body in all fours. Not only was he strong, he displayed the full control of an expert. "This is called doggy style, you'll love it," he said. He inserted back his big meaty cock into my girl as she gasped.

Cindy faced me again looking for some signal. I blew her another kiss, smiled and moved my lips, "I love you, babe."

She smiled back and responded moving her lips, "I love you too."

Now I grinned and moved my lips again, "Relax, enjoy." She understood the message. Jeff was going to fuck her all the way and I would watch. None of us had planned for this. It just happened very naturally, as each of us assumed their role.

He was grabbing her by the hip while gently ramming her on all fours. He began to do it a little rougher. She was panting. He grabbed her by the hair with one hand, and placed the other on her schoolwide famous butt. "You're a lucky man, Zack," he said. "Your girl is smoking hot." Suddenly, he raised the hand and slapped her in the ass. Cindy let go a moan, and did not protest. "Oh yeaah, girl," he said, while slapping her other ass cheek. She let go another moan.