Her Big Regret

The following story is based on true events:

I had just turned 40 years old and was in the midst of a mid-life meltdown. It was triggered by a Facebook encounter with a girl I dated during my college years some 16 years earlier. It was my biggest regret from that time that I never had the pleasure to make love to her. My memory was a bit fuzzy and I couldn't remember why we never made it to bed. I e-mailed her and after a long chat session she said she wanted to sleep with me badly, but felt my heart was with someone else. That someone else was another girl I was dating at the time who eventually became my wife.

My wife, Mattie, after 15 years of marriage, could easily sense my melancholy mood and quizzed me about it, concerned. Thinking honesty was the best policy, I confessed my regrets. Boy was that an error in judgement! She became angry that I contacted a former girlfriend. I tried to assure her it was all innocent and she came back with: "Well how would you like it if I contacted one of my regrets?"

"Who would that have been?" I inquired.

"Mike."

"Mike who?"

"Mike D'Amato."

"Who was he?"

"He was the pool manager where I lifeguarded the summer before we became engaged."

I remembered that summer well. I was finishing school and Mattie graduated and moved back home to work. Since we were far apart, we agreed to allow ourselves date other people to make sure we were ready to commit.

"And what did you regret with him?" I asked.

"Not sleeping with him."

"Really?" I was intrigued. "And why didn't you?"

"Well...he scared me a little....He was a really big guy."

"Well I'm 6'-4" and I don't scare you. Did he have a temper or something?"

"No..." she paused "He had a really big penis."

"Really!" I was even more intrigued. "And how did you come to find out this information?"

"The pool staff went to a party at his house after work one day. We had flirted all summer, but it was playful, nothing serious. He was cute but I really wasn't into him. He was older. But after a few drinks we found ourselves in his bedroom all alone. We started kissing and fell into his bed. We were letting our hands roam, and he eventually undid his pants. He pulled down his underwear and exposed his penis. It was huge. I never had seen one that big before. (I didn't really watch a lot of porn back then). Anyway, I got scared and left. I was afraid he would hurt me. I always felt bad for running out on him the way I did. I thought he deserved an explanation after all the flirting we did that summer."

Mattie was a knock-out back then. She was a 5'-4" Italian beauty with long naturally-curly black hair and a dark cream skin tone that quickly turned to a deep bronze after a few hours in the sun. She had curvy hips and a muscular swimmer's ass that filled-out a swim suit nicely. She had full 34-D breasts with brown silver dollar-sized areolas and large nipples. She had green eyes and a radiant smile. But her best feature, in my opinion, was, and still is, her vagina. The patch of skin between her legs was naturally dark. She kept a soft trimmed bush above a long slit that was brown with a dark violet hue. And when she became aroused, the darker outer lips would swell, exposing a dark pink clit and moist pink inner lips. Between her ass, hips and vagina, she was built to take a large cock and make babies.

I imagined time and again what it would be like to see her vagina stretched to the limit. Sadly, I don't have the cock to do it. My penis is a very modest 5-1/2" long and is only slightly thicker than the diameter of a quarter when fully erect. I can fuck her until the cows come home and she only achieves orgasm when she masturbates herself at the same time. And even then, she's on her back with a pillow over her face fantasizing about God knows who.

The thought of Mattie getting taken by such a large cock had my mind swimming in a sea of emotions: part lust, part envy, part shame...but oddly enough, not jealousy. "So what happened then?" I asked.

"Nothing really. It was the end of summer and you and I hooked back up and got engaged. He married someone; I don't know who. But I recently heard from a mutual friend that he was recently separated."

"So why don't you now?"

"What? Have sex with him? Now?!" she replied shocked at the suggestion.

"Sure, why not?"

This turned into a long discussion. I argued that we were 40 years old and not getting any younger. Didn't she really want to know what it would be like to have sex with him? Was it cheating? Not if I gave my consent. How would fucking another man affect our marriage? Not at all. I wouldn't get jealous, and I know she loves ME. In fact, I often fantasized about her with other men. I had tried to use large vibrators on her before, but she always said they were uncomfortable because they weren't real. Now she had a chance to find out what the real thing feels like. Think of it as a masturbation session, I argued, except with a real penis instead of a rubbery vibrator.

After several days of less-than-subtle badgering and convincing that having sex with Mike wouldn't damage our marriage, she finally relented. She called him to meet her out for a drink. They met and Mattie explained why she left his room all those years earlier. He said he understood; she wasn't the first girl to run when they first set eyes on his penis. And then she said she wanted to make it up to him. After 15 years, she still looked fantastic. There was a little gray in her hair and her boobs weren't as firm; but I have to give her credit, she still looked stunning. Needless to say, Mike jumped at the opportunity. She came back and said he gained a few pounds but was still handsome. And he still had a potty mouth.

"Potty mouth?" I asked.

"Yes. One of the reasons I kept him at arm's length was that he had such a vulgar mouth. That side of him was a complete turn-off. I mean, he tried to keep it clean around me, but when he drank too much that little filter in his brain shut down. And he was so cocky too. He was always telling me how great the sex would be if we hooked-up (to put it politely), but I just blew it off as bravado. I guess I'll find out Friday night if he was just talking shit or not."

I pulled her into bed and we had a lively sex session. The thought of her getting the big cock she craved made us both hyper-aroused. Usually the only way I can get her to orgasm is if I go down on her. That's usually how we started; but she immediately pulled me between her legs and guided my hard penis into her moist opening. As soon as my cock slid to the hilt, she let out a slight whimper. I stroked in and out of her a few more times and the whimpers grew in pitch. The thought of her finally reaching orgasm with my cock working solo was too much for my overstimulated brain. I lost control and blasted the walls of her pussy with my semen, groaning with each slowing thrust, until finally slumping on top of her.

She let out a whimper that conveyed disappointment. She needed release. I immediately shuffled down between her legs and found her swollen clit with my tongue. I started by lightly caressing it, but then felt her hand pressing on the back of my head, forcing my face harder into her slit - she wanted it rough. I increased the pace and force on her vaginal hood and a gasping response of "Oh yes!" told me I was meeting her need. When she pushed up with her hips and increased the crescendo of her moans, I knew she was close to climaxing. Without my tongue missing a stroke, I pushed her hips back down to the bed and forced a leg back with one hand to expose her moist slit. With my other hand I pushed two fingers deep into her soupy pussy and stroked them in and out to get them lubricated. I pulled my fingers out and moved them down to her brown puckered opening. I could feel it quivering as I started to gently finger her. This was the trigger she needed. Her ass came off the bed in a series of pumping motions that moved in time to the loud moans of ecstasy that signaled her release. The pumping slowed and she gently settled back down on the bed and motioned me away from her sensitive vagina. She lay there splayed open, resting in the afterglow of her orgasm.

The rest of the week was spent reinforcing the assurances I gave her that I was okay with her spending the night with Mike. But all I had to do was guide her hand to my rock-hard cock to give her the assurance she needed. I made her promise to tell me every detail, down to the nitty-gritty. I could tell she was still hesitant, but her curiosity won-out and she agreed to go through with it.

When she left Friday evening, I could tell she was excited. As she showered and dressed, there was a bounce in her step. We both were nervous with anticipation. She wore a hip-hugging black skirt (with no panties) and a matching blouse that nicely accentuated her figure and showed-off her cream-colored cleavage.

Before she left, she pulled me close to her, looked me straight in the eye and asked one final time: "Are you sure?"

"Yes I'm sure!" I responded with a hint of impatience.

"Ok...because if I do this, I'm going to do it... .and have fun doing it," she said in a tone that betrayed her eagerness.

"I hope you do sweetheart," I said, injecting an enthusiastic inflection in my voice to cover the growing lump in my throat. I was still wrestling with my emotions; but I didn't want to convey that to her in the slightest, lest she sense my reticence and back-out. And to accentuate the point, I smacked her butt as she stepped through the front door and wished her a good time. I watched her tight ass shake in her hip-hugging skirt as she made her way to the car. Damn she was hot.

The next four hours I waited with my mind in a fog. I watched a ballgame but had no idea of the score or who was even playing. Or what game it was. All I could think about was what she was doing to him. Or more importantly, what he was doing to her.

Finally, the front door creaked opened and I immediately hopped-up to greet her. She slowly stepped into the foyer, brushed past me, and started down the hall to the kitchen.

"Are you okay?" I asked following her.

"I need water. I'm so dehydrated," she declared.

"Well...?" I asked impatiently, "How was it? Was it as good as you hoped?"

She stopped at the kitchen counter and stared-off into nowhere. "Better..." she replied with a hint of a grin on her face.

I was never more aroused. I moved to embrace her. I dropped my hand to feel inside her skirt and she stopped my arm. "Not yet honey, I'm still a little sore," she said backing up with a hand covering her lower abdomen. "I'm also tired. Let's move to the bedroom and I'll tell you all about it."

I could have broken land speed records running for the bedroom, but Mattie seemed intent on extending my agony. She slowly made her way back to the bedroom while sipping on a cup of water. She changed out of her clothes and into a night gown, brushed her teeth, and brushed her hair before finally settling in bed beside me. We propped ourselves up on pillows and rested against the headboard. She recounted the evening's events as follows:

"Mike was waiting at a table in the hotel bar when I arrived. He asked me if I wanted a drink and I said yes, but I suggested we take it up to the room. We had already caught-up when we met before and we were eager to get going. Besides, I was very aroused already and not wearing underwear. I was afraid I would leave a stain in my seat. We entered the hotel room and set our drinks down on the table. Neither of us took another sip of them the rest of the night. I turned to face him with my back to the bed and he stepped forward and embraced me. We started kissing."

"What was that like?"

"Different. He has a mustache. It was nice. But I really liked his cologne. It smelled good. You rarely wear cologne, so it was a treat."

"Go on."

"His hands moved down to my ass and he pulled up my skirt. His hands roamed over my bare ass and when he realized I was pantyless he said 'Nice!' His hands moved between us so he could feel between my legs and I instinctively backed away (really because it tickled). I said 'Hold on' and laid back on the bed. I bent my knees so my skirt would fall down my thighs. He took the hint and laid down beside me. We started kissing again and he let his hands drift between my legs. It felt different. He has big hands. He rubbed me (I was sooo wet..) and he pushed a thick finger inside me. I almost came right then. I really wanted him."

"You mean his cock? You were ready for it?"

"Yes... I sat-up on the edge of the bed and removed the rest of my clothes. He was getting undressed and he told me to undo his trousers. His pants were extended out so I could tell he was aroused. I unhooked his belt, unfastened the button and pulled down his zipper. I had difficulty removing his pants because of his penis, so he pulled them down for me. That's when I saw his cock for the first time. I mean, I saw it before but it was soft then. Now it was fully engorged, long and thick and angry. I was thinking 'Ohhh shit, I'm in for a long night'.

"I think he noticed the hesitation on my face. I'm sure it's not the first time he's seen that surprised look. He gently grabbed me by my hair and pulled my face to his cock. I tried to take him in my mouth but could only manage to get the head in. I could taste his pre-cum. I bobbed up and down on the head a few more times, but my pussy was aching; I was ready. I laid back on the bed. He asked me if I was ready for his big dick. I whispered 'Yes'. He moved up between my legs and started moving the head of his penis up and down my slit. I guess he wanted to lubricate it so it went in easier, but it felt really good. I remember thinking how heavy it felt. I asked him to be gentle and he said he would never hurt me. He then pushed forward. I felt him pressing into me, but he wasn't quite hitting the spot so I rolled my hips up a bit... and then it hit home. I felt my pussy start to open. He started working it in with slow gentle thrusts, but it wouldn't go in at first. Then he pushed harder and I felt my opening give as he sank into me. I came immediately from the sensation. God he was big... I must have cried-out because he stopped to see if I was okay. I said I was fine under my heavy breathing and he continued pushing into me with short slow deliberate strokes. He kept repeating how tight I was while slowly working his penis into me."

"Did it hurt?"

"Yea, a little. Obviously my body never had anything that big in it before, but it still felt really good. I guess it hurt in a good way. It's hard to explain. I had to stop him from going too deep, so I wasn't able to take him in completely the first time (but would soon enough!). But he definitely went deeper into me than anyone else had ever been. He stroked in and out a few more times. I felt him get rigid, he started panting, and he came in me."

"Did you come again?"

"No...not that first time. I think the slight discomfort and worry he would go too fast kept me from relaxing and finishing again."

"So then what?"

"We laid there and talked for a little while to give him time to recoup. He started playing with my boobs. I laid back and he started licking and sucking them. He complemented me on their size. He was beside me on his knees and I could see his penis hanging between his legs. (He has a large sac too). I reached over for his cock to stroke it and it started coming back to life. I told him to lie on is back. I moved between his legs and grabbed his cock with both hands and started stroking and licking it. I took the head in my mouth and rubbed the tip of my tongue up and down the slit. He must have really liked that because his dick got really hard and he kept telling me how good it felt. Sucking his penis was getting me wet again. I sucked and stroked him up and down a few more times and told him I was ready.

"I laid back on the bed and he moved up between my legs. He told me my pussy was too tight and I had to help him by opening it up for him. I reached down with one hand and pulled my lips apart and reached for the end of his cock with the other. He pushed forward and I guided him into my opening. It went in easier this time. Jesus it felt good. He started pumping in and out faster than before with longer strokes. My body was more relaxed and I surrendered to his size. He lasted a lot longer. And he kept talking, asking me how good his big cock felt and if I was ready to cum for him again. I wasn't used to that (you're always so quiet). It was a turn-on. I guess it was his confidence. It seemed every time I caught my breath to blurt out a 'yes', I came on cue. He made me finish three times."

"What do you mean by 'surrendering to his size'?"

"Well, normally when you and I are having sex, I have to use my vaginal muscles to squeeze down on you. Then it gets to feeling really nice. But while it feels good, it takes concentration and I lose a little focus achieving orgasm. But with him, my muscles were stretched to the limit. I couldn't have squeezed them if I wanted to. I was able to lie back and focus on the sensation of his penis massaging my pussy."

"Were you loud?"

"He told me later he was tempted to push a pillow in my face to quiet me down. He said I was whimpering loudly and making almost pleading moans. I knew I was loud, especially for that last orgasm. For the first two he still didn't have his cock in me all the way (which I couldn't believe). He was sitting upright stroking in and out of me at a slow steady pace. He asked if I was ready to feel his entire 9 inches. It was already feeling so heavenly, I told him 'I don't care, just don't stop fucking me'. He lifted my legs higher and spread them back further opening me up. He flattened-out his body and eased forward. I felt him go in sooo deep. It felt like he reached my stomach. But what really felt good was his penis is thicker at the base so I could feel it open me up even wider. I came so hard. I never knew sex could feel that good. He must have felt my vagina spasming around his penis, because I suddenly felt his cum hitting deep inside me. It felt warm and soothing. He said I screamed so loud he thought he hurt me. I assured him that wasn't it at all."

"So that was it?"

"No...He made me orgasm so many times my eyeballs were dried-up. He got us some water and I decided to jump in the shower before I left. He joined me and we washed each other off. He's even more of a water hog than you. I started stroking his cock, using both hands. He said he didn't think he could go again, so I sort of took that as a challenge. I got on my knees and started licking his cockhead and gently massaging his shaft with my lips. He rested a foot on the tub and I reached up and started stroking his sac. His eyes were closed and he was moaning. I found the soap and lathered-up my fingers. I gently rubbed his balls and delicately stroked my index finger between his sac and his anus. I know how much you like that. He definitely wasn't shy. He told me to finger is ass. I lubed up my index finger with the soap and found his opening. He pulled his ass open and I pushed my finger up to the first knuckle. 'Deeper' he whispered, so I pushed it up further through his tight opening. I felt-out his prostrate and gently stroked it, eliciting a loud moan in appreciation. Meanwhile, his cock was getting almost fully erect. I went back to stroking his dick with one hand while keeping a finger in his ass with the other. It was hot making his penis hard again. I couldn't help but admire it. It was so thick and full. I couldn't get my hand all the way around it; it was easily as wide as my wrist. And the head was swollen to the size of a plum. I told him I needed to feel him inside me again."