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First time (a true story)
02/06/2015
‘Baby?’ Jenn asks. ‘Yes?’ I say.

‘Is there really a guy coming to fuck me?’

I smile and squeeze her hand. ‘Yes.’ I say, looking deep into her eyes. She sits up on the sofa and plants a kiss on my lips. It’s a loving kiss, but it has more conviction in it than any she has given me in the past few months.

We were in a dry spell. It was as if we were roommates who were getting sick of each other. That is, until last week when she found my flash-drive.

My flash-drive, a black 4 gig SanDisk, was my dirty secret. I kept it taped behind my desk, so Jenn wouldn’t find it, and I was terrified of what would happen if she did. Would she think I was a pussy? Would she leave me?

Almost equally as terrifying was the thought of her actually wanting to cuckold me. It was a really hot fantasy, and one that in the moment, I would desire more than anything. After I came, however, was a different story. How would I feel if she liked it? What if she LOVED it?

Our lips break away, and she wrests her hand from mine. Her eyes close as she pinches her nipples between her fingers. I watch, knowing she is thinking about him.

Jenn found the flash-drive while looking for an outlet to plug a spare phone charger into. Ironically enough, had it not been hidden, she probably would have never looked at it.

I suppose I can’t blame her. I would have been curious as hell too! She had all day to peruse the contents of my cuckold mind, and when I got home, my worst fears were realized. She was confused, hurt, and completely aroused.

We sat and talked for hours. She wanted to know if I was gay, which I assured her I was not. She wanted to know if I wanted to be with other women. I assured her that I didn’t. She wanted to know if I still loved her, and to this I told her I love her with all of my heart. Finally, she asked me why I found it so erotic.

I had to think for a while. I had never tried to explain it to anyone before. I told her that I found her so attractive that I wanted to not only be with her, but I wanted to share her with others. I explained that it is a combination of loving the way jealousy feels, and wanting others to experience what I have. I told her I wanted to see the pleasure on her face, when a man gives her a style of love making that I could never give.

By the time I had finished explaining, I had not only convinced her, I had convinced myself. Her next question was really easy to answer. “Baby,” she said softly. “Would you like to try it?”

The ‘yes’ flew out of my mouth faster than I had ever imagined it would. She seemed taken aback at first, but then, as if weighing the possibilities in her mind, the corner of her mouth curved upwards into a tiny smile. Her eyes danced.

“Where can we find someone?” She asked. I suggested craigslist, but she shot that down immediately, wrinkling up her nose at the idea. There were other dating sites online, however she said that she would rather do it with someone we are both comfortable with. This left us at an impasse. Who could we choose? It would have to be someone we both trust to be quiet about it, someone who I wouldn’t mind losing as a friend if things became weird, and someone who Jenn found attractive.

“Let’s look at my Facebook.” I suggested. She agreed, and I was surprised when she got off the sofa first, and dragged me into the bedroom. I sat behind the computer; the disk drive was still flashing in the USB port by my leg. I looked at Jenn sheepishly and she gave me a look that said, ‘you dirty little boy.’

I logged onto my Facebook, and Jenn sat on my lap. Opening my friends list, I filtered it by men and we started scrolling down. Every now and then, Jenn would point to a profile and I would open it up. My cock jumped in my pants every time her hand moved towards the screen. Sometimes she would say “never mind,” sometimes “maybe,” but three times she told me to “put him on the list.”

When we got to the end of my friend list, we had three names written on a post-it note. I opened their profiles and we started looking through their pictures. One we eliminated right away, when we realized he knew mutual people besides me. Another had gained some weight since his picture was taken. The last one was a friend of mine from about 10 years back named Devon. He lived one town over and was a tall, skinny black man, with a personality that wasn’t too ghetto.

“I want him.” Jenn whispered in my ear. My cock stiffened in my pants, and she took the mouse from my hand and opened up a new chat box with Devon. “How are you going to ask him?” She asked me.

To be honest, I hadn’t the slightest idea. I thought about all the ways we could hint at it, but decided that the best way was direct honesty. He was online at the moment, so I figured there was no time like the present.

‘Hey buddy!’ I typed. We sat breathless, as we waited for a reply. Suddenly, we could see that he was typing. ‘Sup bro?’ he responded. Jenn’s left hand pinched her left nipple. ‘I have a question for you.’ I wrote. My heart was pounding. ‘What?’ he responded. It was the moment of truth. I looked at Jenn, she was in a trance, but she squeezed my leg with her right hand.

‘This is going to sound really strange, and I hope you don’t take this the wrong way, but my girlfriend thinks you are hot, and we are both interested in her being with another guy… so are you interested?’

There was a long pause. The message said it had been read, but no reply. My hand was unconsciously rubbing my cock thru my pants as we both stared at the screen. Finally, after what seemed like minutes, he replied with ‘for real?’

I swallowed hard, and typed the word ‘yes.’ He responded quickly this time. ‘Text me a pic!’ Jenn and I went through my phone in a hurry to find a picture she liked. I attached it to a text and sent it. A little bit later he sent a text back saying ‘I meant a picture of her naked.’

I showed the text to Jenn. She had always refused to let me take naked pictures of her, but as if she had become somebody else, she got up without saying a word, took her clothes off and laid on the bed with her legs spread apart.

‘Are you sure?’ I asked. She delicately rubbed her index finger on her clit and moaned ‘yes.’ His response was fast. ‘I can be there at 10 tonight.’ There was a moment of fear in Jenn’s eyes, but her finger washed it away as she continued to masturbate on the bed. ‘Tell him 10 works,’ she squeaked out.

I sent Devon the confirmation and he responded back with a winking emoticon. This was all happening so fast. I lay down beside Jenn and took my clothes off. My six inch cock was harder than it had ever been. I had to have her.

Straddling Jenn, I bent in and kissed her. She kissed back with such ferocity that I thought she was going to bite my lip off. With both hands on her shoulders, I pushed her back into the pillow, and plunged my hard cock into her wet pussy. Her hips rose to meet me as we had the wildest sex of our relationship.

She came, and I decided to hold off, as I didn’t want to change my mind after an orgasm. I looked at my phone. It was only 5 o’clock. Dropping the phone on the bed beside me, I rolled over and looked at Jenn. ‘Are you sure you want to do this?’ I asked. ‘Are you?’ She countered. ‘Yes, but only if you want to.’ Jenn took my hand and guided it down to her pussy. ‘Feel how wet I am,’ she cooed. ‘I want to.’ She whispered in my ear.

I was still hard, and I tried to mount her again, but Jenn pushed me off. ‘I don’t want to be too sore for him.’ At that moment, I had my first pang of cuckold anxiety. She turned her head away from me and rolled over. ‘I’m going to take a nap,’ she said very matter-of-fact. ‘Can you go get some more moscato? We are all out and I don’t want to do this sober.’

Feeling like a scolded child, I uttered a frustrated ‘yes’ and stuffed myself into my jeans. My erect cock was painful against the denim as I walked to the garage. I expected to hear a goodbye from her as I left the room, but all I heard was her breathing.

During my drive to the store, I started to second guess myself. ‘What am I doing!?’ I screamed in my head. Am I really about to let the woman I love fuck another man? What if he is bigger than me? What if she wants to keep seeing him? What if… what if…

I got home, and Jenn was back on the computer. She didn’t look up when I walked in. Hey, she said in an indifferent voice. She was looking through the cuckold captions on my flash-drive again. One of them showed a freshly fucked vagina with cum flowing out of it. The caption read ‘Your turn cucky.’

She turned and looked at me with a confused look on her face. ‘You see, this is why I am wondering if you are gay.’ She said. I sat on the bed and explained to her that it is a submission thing, and that I don’t really like the taste of cum (I had tried my own) and that the only reason it’s hot, is because I am doing it for her pleasure, not mine.

Rolling her eyes, Jenn shot a sarcasm dripping ‘Okay’ at me. ‘Are you into everything on your flash drive?’ She asked. ‘Some more than others,’ I said timidly. There was some really strange stuff lurking on that little thing.

Jenn turned the screen off and walked past me to the bathroom. She left the door open, and I saw that she was putting on make-up. Make-up for him. My cock stirred in my pants again. ‘He has to wear a condom.’ She said. Somewhat disappointed, I readily agreed.

‘I still don’t know why this turns you on so much.’ She said. ‘I will try it just this once, but if I don’t like it, I don’t want to hear about it again.’ Again, I quickly agreed. ‘Can you pour me a glass of wine baby?’ ‘Sure!’ I said, excited that we were changing the tone of the conversation.

I poured her a generously sized glass of moscato, and brought it to the bathroom. She was just putting the finishing touches on her lipstick. ‘Thanks hun,’ she said. ‘Now go and close the door, I am going to shave my pussy.’ ‘Can’t I watch?’ I complained. ‘No, this is for him tonight.’ She shot back. Jenn had never talked to me like that before, and I stared in blank surprise at her as my cock tried its best to burst out of my zipper. ‘Go!’ she shooed me away with one hand, and after I closed the door, I could hear her lock it behind me.

I settled on the sofa and flicked on the news, trying to get my mind off of what was about to happen. It was close to an hour before Jenn emerged from the bathroom. She had on her pink bath robe, and was wearing matching pink underpants and bra. ‘What time is it?’ She asked seductively. I looked at my phone. ‘9:00’ I said, my heart sticking in my throat.

Jenn sat on the couch beside me, downed her wine and had me pour her another. That was 55 minutes ago.

‘Baby!’ I snap out of my retrospection and turn to Jenn. ‘What time is it?’ I look at my phone. It is 9:55, and there is a text from Devon that I missed. I open it up, and part of me hoping he was canceling. My cock jumps when I read it. ‘On my way.’

No sooner do I put the phone back down on the coffee table than does the doorbell ring. Jenn looks at me with excitement and whispers ‘he’s here!’ I kiss her and get up to answer the door.

Devon stands in the doorway, an imposing figure, at around 6’2” and towers over me. He extends his hand and we exchange awkward pleasantries. ‘Devon,’ I gesture towards Jenn, ‘this is Jenn.’I see lust in his eyes as he offers a short ‘sup?’ to her. Jenn smiles at him and I see her legs part in an unconscious act of submission.

I instinctively sit next to Jenn, but she shoves me aside and tells me to sit in the wing chair by the sofa. Devon sits in my spot, and runs a large black hand up her creamy white legs. Jenn looks at me, and I nod. She smiles and looks into Devon’s eyes. Their heads bend towards each other and they kiss.

Jenn, normally slightly dominant, becomes totally submissive to him. She lays back on the sofa, her legs spread open, chest heaving, and with a look of wanting that I have never seen in her eyes before. Devon stands up and unbuttons his shirt to reveal his muscled torso. Jenn’s eyes don’t waver. ‘You are so dark,’ she speaks over her breath. He then walks up close to her, and she instinctively unclasps his belt, unzips his fly and undoes the top button of Devon’s pants. I watch in rapt attention as she slides both pants and boxer shorts down his long, muscular legs. His semi-erect cock springs into view.

Jenn takes it into her mouth and sucks on it. The color contrast between her creamy white skin and his dark African cock is AMAZING. It grows to be around 7 or 8 inches and above average thickness. I look at my cock, which has since made its way out of my pants and into my hand, and do a quick comparison.

Devon pulls his cock out of Jenn’s mouth and pushes her back on the sofa. He lowers himself down on top of her, and without penetrating her, they kiss and hump in rhythm. Finally, the moment of truth has arrived. I stop stroking my cock as I see the head of his member position to enter my girlfriend.

They stop kissing as she feels the tip of it against her opening. He looks at her, not me, for approval, and she nods. Never once do either of them look back at me. I am invisible.

His cock pumps in and out of her, she moans and her nails dig into his back. Her legs wrap around his midsection and her mouth locks onto his. Suddenly I realize that he didn’t use a condom! Torn between what I want to see, which is a bare cock in Jenn’s pussy, and what she stated she wanted earlier, I reluctantly say in a feeble voice, ‘don’t you want him to use a condom?’ Devon stops and Jenn looks up at him, then at me, then back to him again.

‘It feels better without a condom.’ Jenn says. With that, she pulls Devon in for another kiss, and raises her hips up to coax him back into the rhythm. That is all it takes. He pumps into my woman for half an hour, giving her multiple orgasms. Jenn screams his name, lost in ecstasy. Finally Devon’s balls tighten up, and I knew what is going to happen next.

Jenn gasps as she feels his hot cum pump inside her. There is so much of it, it starts to leak out onto the sofa immediately. Devon, suddenly sheepish rolls off of Jenn. She doesn’t care. Jenn is lost in a sex coma.

I stand up, my erection bobbing up and down and wet with pre-cum. ‘I have to say thank you man,’ I stammer. He looks at me sideways, and musters an ‘any time.’ Devon, as if suddenly remembering, pulls out his business card and set it on the sofa beside Jenn. ‘Call me anytime.’ He says. Jenn looks at me and then at Devon. ‘I will.’ She replies.

As soon as the door shuts, I sit beside Jenn. ‘How was it babe?’ I ask. ‘Was he good?’ Jenn puts her arm over her head and stares vacantly at the ceiling. ‘yes.’ She whispers. ‘Better than me?’ I ask. ‘Soooo much better.’ Is her sultry reply.

My cock is ready to explode. I get up to mount her and reclaim my woman. She rolls over and says a firm ‘no.’ My face falls. She then says what every cuckold thinks they want to hear. ‘I want you to lick me.’

As soon as she says those words, I come all over her stomach. My cum pools in her belly button, and runs like rivers down her rib cage and onto the sofa. Jenn doesn’t skip a beat. ‘Clean that up too.’ Hesitantly, I lean in to taste my cum first, and, finding it barely palatable, I start to lick her stomach clean. ‘No, not there yet,’ she says forcefully. Her hands grip the hair on the back of my head and push my face up to her red, wet, cum filled pussy.

‘Lick.’ She commands. I reluctantly taste his cum. It looks different than mine, and it has a bitter taste. I recoil, but find my cock hardening again. I gently lick Jenn’s clit, and she shoves my face directly onto her. I lick furiously, swallowing the cum that flows from her used cunt.

Jenn cums again, this time all over my face, sending a mixture of her ejaculate and his right in my mouth. She suddenly pushes me away. ‘I’m too sore now.’ She gets off the sofa, grabs his card and her phone, and wobbling on her rubbery legs, walks to the bathroom. A few minutes later, I watch in disbelief as she, without a word, crawls in bed and goes to sleep. All night long, I hear Jenn’s phone buzzing, and I know it is Devon.

In the morning, we don’t talk much about it, aside from a short ‘that was fun.’ But as I leave for work, I see Jenn pulling out her phone and smiling at what she sees. Her thumbs type quickly, and she giggles, a glint in her eyes. ‘I’m going to work, now.’ I say.

As if startled into reality again, Jenn’s head snaps up with a look like she has just been caught with her hand in the cookie jar. I smile and walk up to her, kissing her on the mouth. ‘Have fun today.’ I say in a playful tone, and with a wink, I walk out to the garage.

Jenn smiles back at me as I leave. I get in the car and realize that I forgot my sunglasses. I stop before opening the door when I hear her on the phone with someone. ‘He’s gone now, I am free all day.’ Gingerly walking back to the car, I get in the driver’s seat, knowing my life has changed forever. I back out of the driveway and head to work with an erection and a worried smile.

THE END


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