Samantha's Story: Online Hookups Ch. 02

It was summer of 2013. Dan still worked a lot, and my daughters were kept busy with gymnastics and various camps. I also kept myself busy, especially since discovering the Craigslist 'Casual Encounters' site.

I had found a good online hook-up with Louis. He could've become a steady partner but I craved different experiences. I continued to search and email back and forth with men who advertised themselves as hung black men who were seeking 'no strings attached' fun.

I posted an ad myself with some sexy selfies with of course my face not showing. I received tons of responses, but it was overwhelming, and it was too hard to distinguish what was real and not real.

By the end of the summer, I had corresponded with over 20 different men before I eventually agreed to meet with two different men who had posted an ad. I met the first one at a Starbucks, but we didn't hit it off. He was pretty good looking and based on his pics was packing a nice cock, but I didn't care for his personality. It was not a comfortable vibe, so we parted ways at the Starbucks.

I met the second man at a small city bar a couple of towns away. His name was Roberto. He was a dark skinned Brazilian in his early 30's. He was more handsome than his pictures and although he talked too much, he was a nice guy. He said that he lived by himself nearby and asked if I would join him. I was on the fence with hooking up with him, but the two wines had an effect on me.

I agreed to follow Roberto back to his home. When we got there, it was a 3-family house in what did not seem like a great neighborhood. I thought of driving away, but I did not want to come across rude. I was hesitant, and too nice and stupid to get out of my SUV, but I did. I ended up following him to the back of the house and he walked me to a basement apartment. From there, it was uneventful. I wanted to get out of there as quick as I could. Again, I should have just left but I remember not wanted to hurt his feelings. In a way, he kind of guilted me into fucking him. It was a quick fuck. I had a dress on that didn't even need to take it off. After we awkwardly kissed, I pulled his pants down and began to suck his dick. It was a nice 7-inch cock - not as big as he advertised but still very serviceable. I planned on just sucking him off and getting out of there but instead, he pulled me up, pulled down my panties, put on a condom, and fucked me standing up from behind. I held on to his kitchen table and he came very quickly. I then put my panties back on and exited without an orgasm.

With two less than successful live experiences with Craigslist, and countless dead-end e-mail inquiries, I began to grow tired of Craigslist.

While taking a brief freak from Craigslist, I began to search for Gayle online. Gayle was a football player I knew in college who I began to fanaticize about after hooking up with Louis at his college apartment. Gayle now lived about three hours away and was a schoolteacher. I found him on Facebook and decided to send him a friend request, and he accepted it shortly after. He did not post much but it appeared that he was a divorced dad and taught middle school. His pictures showed that he was still super-hot. I regretfully did not think of him that way when we went to school, but if I knew then what I knew now what I didn't know then, I would not have hesitated in allowing him to make me be another notch in his belt. He was with a lot of girls during our college years. I remember hearing about his big cock but at the time I just laughed about it. Now, I was looking back with jealousy and regret.

I talked with Gayle a hand full of times during our college years. He was often the life of the party. My husband Dan knew Gayle while we were at college, but he was not friends with him. I look back at the times I spoke with Gayle, I realize how naive and stupid I was. He definitely was in to me but the thought of hooking up with him somehow never crossed my mind - I was such an idiot.

I eventually got the nerve to message Gayle privately on FB Messager with just a simple "Hi there, I hope all is well!"

Gayle responded back soon after with a "nice to hear from you Sam! All's well on my end, how about you?"

We proceeded to message back and forth with a friendly catch-up. A couple days later after our catch-up, I decided to message him again with a "I'm surprised you remember me."

He soon messaged me back "are you kidding? I always had a crush on you in college ;-)."

Gayle's confirmation that he a crush on me sent chills throughout my body. Instead of messaging him back right away I held off and proceeded to break out my big black dildo. After powering it up I stared at a posted photo of Gayle, and I came in seconds.

The next day, I decided to message Gayle back saying, "that's so sweet. I think EVERYONE had a crush on you LOL." I thought it was a good response - it built up his ego and was subtle enough to make him wonder if I was part of that list of "everyone." He responded modestly but I think he got the hint that perhaps I had been into him too. We continued to message back and forth and it became more open and flirtatious.

A week before our college Homecoming in October, Gayle messaged me to see if I was going to be there. I was not planning on it, but after I found out that a couple of college friends were going, I told them that I would join in. I did not tell Gayle that I would be there.

Dan chose to hang out with some friends instead of going to Homecoming and we were able to have our kids stay with my parents for the night.

On the day of Homecoming, I got to the parking lot with two of my college friends that I still saw often. The lot was almost completely full of tailgaters when we got there. After we parked, we each opened a beer and decided to walk around. It was twenty years I believe to the day when I was a freshman at my Homecoming football tailgate. It was a lot different but a lot the same. My friends and I met up with a lot of new and familiar faces.

Shortly before the game was to start, we finally got to the section of the parking lot where all of the football alumni were. I spotted Gayle right away in the crowd. He was still the life of the party. My friends and I socialized for about a half hour before Gayle noticed me. Once he saw me, he came over and gave me a big hug. It was like we were long lost friends. I could tell that the friends I was with were surprised and envious with the way Gayle greeted me - I was no longer the shy girl they remembered in college. I'm certain that it would not have been as friendly of a greeting if I had not reached out to him on Facebook.

By the time I got to see Gayle, the parking lot was about 80% vacate. Everyone was heading into the stadium. He opened two beers for us, and we hung out and talked. I told my friends that I would meet them at our seats - they became too drunk to think anything of it. Before I knew it, I was so into the conversation I was having with Gayle, I didn't realize there was no one left in the parking lot except for some event staff.

We could hear the game begin when Gayle cracked open two more beers. He talked about how much he missed playing football and how watching the team made him sad. Looking into his eyes, I admitted, "I don't have much interest in the game. I'm just here to catch up with some old friends." I did not need to spell it out that the only reason for me being there was to see him. In hindsight, I was practically throwing myself at him.

Gayle asked what I missed most about college. I said, "my friends, meeting my husband Dan and his friends, football & basketball games, parties, Spring Break." Gayle responded back with a similar generic answer. I then said, "I also often think of what I missed out on when I was in college."

Gayle stood up and bluntly said, "I know that I definitely missed out on you." When he stood up, I was reminded with how big he was. At a muscular 6'3" he was still in great shape and based on the size of his hands and feet, and his sexual history, I was at his mercy.

Gayle opened up 2 more beers, handed me one, and walked me toward the backseat of his nearby Trailblazer. He made some room and reached out his hand to guide me in. I looked around and once I saw the coast was clear, I joined him in his back seat. After he closed his door, we each took another sip of our beer. He then took my beer, placed them in his cup holders, and he made his move to kiss me.

After a minute of making out, we each looked out the window to make sure no one could see us. I looked at Gayle and could not believe it. I said, "I can't believe we're doing this. I have to admit. I've cheated on Dan before with other black men." Gayle was amused with my admission. I kissed him again and said, "I've always thought of you. I've always regretted not doing this twenty years ago."

With a big smile he said, "better late than never" as he drove his tongue into my mouth. He then lifted my sweatshirt over my head and pressed his face in between breasts. In the same motion, he unhooked my bra and removed it to expose my tits. He sucked on my tits and hard nipples while I continued to look around to make sure there was no one around to see us. It felt very dangerous and very sexy. "You've gotten even hotter with age," he commented while enjoying my tits which were bigger from when he last saw me.

While he sucked on my tits, I was able to unbutton my jeans and shimmy them off. I then stuck my hand down his pants. It was no surprise that Gayle's cock was massive. While holding on to his huge cock, I looked at him and said, "where was this twenty years ago?"

Gayle chuckled and said, "it was always here for you, you were just too blind to notice."

"That's for sure," I replied as I pulled down his loose fitting Adias pants. Gayle sat back in his seat to pull his pants fully off. I looked at him and was so turned on by the moment. He had on a pair of tight Jockey underwear, and the outline of his huge semi-hard cock was an incredible sight to see. I aggressively helped him pull down his underwear. I held on to his cock and said, "it is more beautiful than I ever dreamed." My lips could not wait any longer. I went down on him and began sucking it with great enthusiasm. It got up to a solid 10 inches by the time I got him fully hard. I went back to kissing him, looked around the parking lot again, and whispered in his ear "I need you to fuck me so bad."

Gayle could not believe his ears. "Are you really the same Sam I knew in college?"

"I'm the new and improved Sam, and I need you to make up for lost times." I surprised myself with these words. I was no longer the little blonde conservative girl that was shy around men. I was now a mature woman who knew what she liked. What I liked was the feel of a big black cock having its way with me.

Gayle recognized my transformation and did not hesitate in giving it to me. He shifted my thong to the side, and he penetrated me. I was so wet and turned on, I pulled him close and "yes! Fuck me hard Gayle, I need that cock of yours so bad!"

Gayle's thrusts were gentle but mighty. He definitely had a lot of experience fucking smaller women like me and he was better than advertised. The more we fucked, the more I cursed myself out for missing out on this opportunity while I was at college. Here I now was - I was in the backseat of probably the hottest guy I went to college with. Staring up at the Trailblazer ceiling with my legs spread wide up, it was a feeling of gratifying bliss. When I came for the second time, the feeling of the organism caused me to rip my thong completely off.

Again, to no surprise, Gayle had great stamina. After fucking me missionary for a while in the crammed back seat I told him I wanted to ride him. He granted my request by sitting up in the middle seat. I rolled over on top of him. My legs were already very sore, so he helped me. When I got on top of him, we kissed again as he guided his huge rod back into my hole. We proceeded to fuck while I looked out the window behind us. I was still on the lookout to make sure no one was watching us. The only people I saw off in the distance were too far away to notice what was happening. With the coast still clear, I continued to fuck Gayle with great joy. When he told me he was ready to cum, I rolled off on him and immediately began sucking him off. "I want to taste you" I said and a couple of seconds later, his cum filled my mouth and ran down my throat.

After a minute or two to catch our breath, we began to get dressed. Once I got everything back on, except for my torn thong, Gayle and I kissed and hugged. I told him that I was happy we were able to connect and maybe we could this again someday. Gayle acknowledged the same sentiment and joked about how much of a "cougar" I had become. It was funny because I couldn't believe how true it was.

Gayle and I got out of his Trailblazer, and I was relieved to see there was still no one around that would have noticed us. It was good timing because just as we began to walk toward the stadium, campus security came by in a golf cart. He told us "You're missing the game and sorry, no loitering in the parking lot during game time." I wanted to answer him back that we were doing a lot more than loitering, but I held my tongue.

Gayle and I parted ways when we got to the gate to meet up with our sets of friends. I walked toward the seats I knew my friends were at. I tried my best to avoid limping. My legs were shaking so bad from the fucking I was just given, I had to hold on to the aisle bar to make my way down. It was almost halftime and so they naturally asked me what had taken me so long. I just said I ended up bumping into people on my way in. There was no reason for them not to believe me and the idea that it was because I was fucking Gayle would have been the farthest thing on their mind. As far as my friends knew, I was the devoted wife my college sweetheart Dan.

On our drive home after the game my friends and I talked about all people we came across that day. Like any typical reunion, we talked about who still looked good and who hadn't aged so well. To no surprised, when they began to talk about the men we saw, my friends talked about Gayle and how hot he still was. They acknowledged the warm greeting he gave me. I just it played off "yeah, we were friends in college, I was surprised how excited he was to see me. I didn't think he'd remember me." I played it off perfect.

My friends continued to talk about Gayle - they each wondered how many women he slept with in college. Both of them admitted that they both wished they had slept with him and asked if I ever did. I replied, "You kidding, you know I never had sex with anyone in college except for Dan. But I'm not going to lie, I do look back at opportunities I may have missed out on." After a pause I admitted, "I do wish I had sex with a black man when we were in school."

When I said this, my friends busted out in laughter. It was like the funniest thing they ever heard. "Yeah, sweet and proper Sam, going black! That's hysterical!"

I played along with them by saying, "and yeah, Gayle did look damn good. Looks better now than in his wide receiver days."

This made my friends laugh even harder as they never saw this side of me. In joking fashion, the other friend had to squeeze in the old phrase, "yeah Sam, you know once you go black, you never go back." I wanted to acknowledge how true that statement was, but I continued to play it off cool by just laughing along with them. In my head, I reflected on my encounter with Gayle - I was still sore, and I thought about the taste of his cum.

After my Homecoming encounter with Gayle in 2013, I often thought of him. We kept in touch with one another on Facebook but just as friends. I believed him that he would keep it secret and for all I know, he did! My encounter with him also raised my confidence level. I continued my pursuit for more black men like it was an addiction. Despite my perfect looking suburban life, I could not get enough. Looking back then and now, I recognize it is an addiction and a habit I still can't shake in 2025.

To be continued...