Please enjoy New Friends Make Great Friends – Pt. 1 before reading. Note, the sexy part starts at the *** if you want to skip my detailed set-up.
Valentine’s Day arrived after a week of unrequited desires and listless need, but because the party last weekend required us to have babysitting we weren’t able to have a date night again for V-day. It wasn’t a problem for me, it was a long week and I wasn’t up to going out, I was happier to stay home and enjoy the take-out Derek brought from my favorite restaurant. As soon as the kids drifted off to sleep Derek and I made some cocktails (this is becoming a regular weekend thing I think) and put on our favorite show on Netflix for our intimate evening ahead.
Around a half hour after the kids fell asleep I felt my first wave of tired hit. I was determined to stay up and give my sexy husband a nice Valentine’s fuck session but it was going to be really hard. I was roused by the ping of a message on Derek’s phone. James messaged that he was coming to town. He was on the hunt, apparently things with Lily didn’t seem to progress as they should by that point.
In an effort to catch a little snooze without feeling like I was keeping Derek from a good night I suggested that he play “wingman” for James. No question, James was a nice guy and he deserved some fun on Valentine’s Day after thinking Lily was going to be someone special. Since I knew I had Derek coming home to me later, it was an easy decision to catch up on some needed rest and let the guys have fun. I fell asleep pretty much right as Derek left the house.
I woke a few hours later to light shaking of my shoulder and a little finger poke to my ribs. As I came to I smelled alcohol mixed with leather and marijuana, just in wafts of air circulating in the room, and saw my husband’s face up close to me. “We’re back. James gave me a ride home. You should come out here and hang out with us.”
I didn’t consider it. I was still mostly asleep. Why? Derek left the room.
Admittedly, earlier on in the night I had thought it would be fun if Derek brought him back and we hang out a bit. And by “hang out” I mean curing that orgy need that had built over the week. But, the unfortunate reality of it was, I was a few days into my period, so while I was a fuck-ton metric buttload horny, I was going to avoid period-sex with a new guy after what happened last time.
I heard a whispered voice again, “why don’t you just come out and hang with us for a little bit…maybe you can give him a blowjob? I showed him your tits, he thinks they are great.” I was thinking it might be a dream, or some flash back to what happened with his other friend. But no this was the reality of my life. I was coming back to my senses.
“I’m just too tired. I think I just want to go back to sleep.” As I released the words there was a bit of regret already.
“Okay baby, whatever you want. I’m just going to hang out with him for a little bit then come to bed.” Derek left the room and joined James in the kitchen for one last beverage. I laid in bed contemplating my options…. Then I got dressed (in jeans and a sweater over a tank top) and went out to say hello. You know me, I like to be a good hostess!
The guys seemed both surprised and pleased to see me. The look Derek was giving me as I sat down made my nipples hard and I looked down to see it very visible, since I had chosen to not wear a bra.
We chatted a bit sitting at the table. Right away I was glad I got up from my nap as the conversation was funny and the guys were keeping me very entertained. It was nice getting to know James a bit better, and I felt even more like we could all be really good friends. But then we heard the cries of our youngest child. As I started toward the kid’s room Derek jumped up and took my arm, whispering, “why don’t you stay, flirt with him, get this started.”
Initiating things in life, I always leave up to other people. I may be one of the most easy-going friends you’ll make, but I’m not the go-getter that makes things happen. But I was going to give this a shot.
I sat down again at the table and started one of the most awkward conversations I am ever going to have. It shouldn’t be awkward, right? I could have said something like, “so Derek told me you like my tits, do you want to see them?” Then I pull them out and he moves in. Or I can get really naughty and ask him, “do you like MILFs?” That would probably elicit a laugh and further awkwardness but it gets a point across. But no, in an effort to give you full details here is what I said, “so, Derek told me that he told you about us….” Then I suffered from frozen brain, embarrassment, and slightly stimulating humiliation… “I mean, um, (short pause, I giggle a little) he told me that he told you that we….” This discombobulation of words actually hurt my brain a little. I can’t say them, I can’t say the words, any of the bad naughty words.
James looks at me and laughs. “What are we talking about?” He is cute. Wow, he is actually really cute! This is scary.
Derek enters the room and the nervous energy deflates a little into a better haze of feelings. “Dude, thank you, this was just one of the most awkward conversations I’ve ever had.” James says, causing us all to laugh.
Of course, Derek comes to our rescue, saving the night by actually being able to utter the words I was not able to, words like “swinging”, and “like to have threesomes with dudes.”
James explained that this was his first time having a threesome, or whatever this is, so this is all new for him. I attempted to explain that this experience was really different for us, because usually we meet our partners on Casual Encounters. I said, “either way, when you get to the moment, it is always somewhat awkward to get things started.”
James smiled and said, “so with the other guys, how do you eventually get things started?”
I answered quickly, “we all just sit on the couch. Then Derek takes out my…titties.”
James is a smart young man, giving us the quick reply, “so let’s move to the couch.”
Without hesitation we all moved to the comfortable brown couch. James took the corner spot and Derek sat far to his left.
I wish I could say that I did a sexy little slide in between the men, or better yet, a nice little dance while I strip. But I didn’t, I worked in an abrupt friend-like hug (tall girl standing up to a guy sitting down) and maybe kiss on the cheek before I sat down across from the men, facing them. Then I just decided to get on my knees, and started taking my boobs out.
Derek, my wingman, watched me work my way through this awkward moment. Again, not the sexiest I’ve been during a sexual encounter. But regardless of what I looked like as I tried to keep my tummy covered, I really was getting turned on by them watching me. Then as both men started touching me, and kissing my chest and shoulders, I felt like I was floating again. I love this feeling.
I caught a few kisses on my lips, James worked his tongue in my mouth passionately. I felt him pull me in as he kissed my neck, and all around my ear, finally tugging a little on my lobe just like I love. Hearing his breathing made little whimpers escape me. It was getting really hot fast, feeling both men take my body was making me sweat and shake.
And then we were interrupted by a cry for “mommy!”
I sighed as I rose to take care of my little one, but again, my husband hopped up to leave the room, letting me to navigate the flow of the encounter. I wasn’t sure where to settle in again as I sat back down, so I chose to face James more on my knees again, and asked him to take off his shirt.
I ran my hands over his body leaving a trail of soft kisses in my wake. His skin felt so soft and warm, and smelled so clean. I tried to appreciate each tattoo I encountered over his shoulders, and down his arm and back again. Each piece was a great work of art.
I continued caressing this new body before me, and eventually my hands ventured down over his jeans, locating a substantial bulge.
“So are we going all the way here?” James asked a great question, but I hated to answer.
“I can’t tonight. It isn’t good timing…but I really want to make you cum if that is okay.”
One of those questions I don’t need to ask maybe, I didn’t wait for his answer as I started unbuckling his belt, then his button, then his zipper. In one swift motion I pulled both his pants and boxer briefs off, and exposed the first uncut cock I’ve seen, and it was thick, and he was shaved so clean, it was a beautiful sight.
“Wow, it is really nice.” Again, searching for words and blurting, “I knew you would have a big cock.” As if I needed to say more, “and I’ve never touched an uncircumcised man before.”
Derek was able to return to the room right then, and got close to watch me learn how to work James’ tool. Eventually, and with some instruction from him, I figured out to hold the extra skin at the base, and work my mouth and other hand up and down the shaft. I started really getting into it because I could feel his hands in my hair
I loved the velvety soft head, it was strikingly different than the circumcised men I’ve been with. The sensation in my mouth sent electricity through my body. I wanted more, as much of him as I could get in. And I did get it all in, surprisingly, with some effort and a lot of breath holding I managed to deep throat him.
Holding power of this man while man husband watched, moving my fingers lower and watching for his reaction to new things I’m trying, it was intoxicating. But then he took control, and fucked my face, then pulled off and jerked off, then fucked my face more. Until my husband knew it was getting close, and told him to shoot it all over my titties.
He came in huge spurting waves, holding me tight and fucking my cleavage through each one. Finally, after covering me, he pulled off and exclaimed that it had been one of the best orgasms of his life. I proudly got up, making sure he got a towel and went to clean up myself.
As I came back out he was getting ready to go, and I made sure to let James know that I had a great time and wanted to see him again. Next time we would get to do more. I was high on endorphins, so I’m not sure what else was said. I still hadn’t orgasmed but I wasn’t going to that night, sometimes I like to ride the deprivation.
Except the next day I just couldn’t take it. After fucking myself with a glass dildo out of desperation, I begged my honey to send James a message. I wanted more.