My Wife with Another Man - Thrills and Regrets

by Flash of Stocking

Caution: This Erotica Sex Story contains strong sexual content, including Reluctant, Cheating, Slut Wife, Cuckold, Pregnancy, Voyeurism, Size, Leg Fetish, .

Desc: Erotica Sex Story: I've always fantasized about my wife with other men. Jen's always thought I was crazy. Sometimes, though, she humors me by fantasizing about other men while we're making love. One guy we liked fantasizing about is Ralph, who is married to Lynn. Things got interesting (and complicated) when Ralph and Lynn divorced, and my wife, with my encouragement and blessings, spent more time with Ralph.

Chapter 1

I've always fantasized about my wife with other men. Jen is no prude but she's always thought I was crazy. I'm certain she's been completely faithful to me for the 10 years of our marriage. Sometimes, though, she humors me by fantasizing about other men while we're making love.

One guy we liked fantasizing about was Ralph, who was married to Lynn. Whenever we'd get together Ralph would flirt with my wife, and she loved the attention. Ralph is handsome and athletic, and I know Jen finds him attractive. It took months before Jen allowed us to add Ralph to our bed-time fantasies. Up to that point we always fantasized about nameless people, and she didn't feel comfortable about fantasizing about someone we knew, especially someone we saw all the time. But fantasizing about someone I knew Jen was attracted to was a big turn on for me. I kept bringing Ralph up, and finally Jen started letting us include him in our fantasy life.

We often hung out with Ralph and Lynn, either as couples or with our families (we each had 2 kids). I encouraged this, because I liked seeing Ralph flirt with Jen. As we became better friends, Jen even started flirting back. It was friendly, harmless flirting, but watching Jen giggle like a school girl at Ralph's jokes, and lightly graze her finger tips along Ralph's back gave me an incredible hard-on. We had great sex that night.

About a year ago Ralph and Lynn started having marital problems, and it ended with Lynn separating from Ralph. Lynn went off to find herself, and Ralph was left at home with their 2 young kids. Jen is a stay-at-home mom so she helped Ralph with his kids when she could. Sometimes she'd pick up groceries for them, or help with driving Ralph's kids to their after school activities. This caused Jen to spend more time with Ralph.

You can imagine how this fueled my fantasies. I loved it that Jen was spending time with Ralph. I encouraged her to dress sexy around Ralph. She thought I was crazy, but after a lot of cajoling she finally agreed. She couldn't go too far without being obvious, but she began wearing tighter jeans and tops. Sometimes she'd even wear short skirts and heels. It was thrilling thinking of Ralph getting hard looking at my sexy wife. At night I'd pepper Jen with questions. She'd always roll her eyes, but eventually she'd tell me if she'd caught Ralph stealing a look at her legs or down her blouse, and we'd have great sex.

It didn't surprise me that Ralph found my wife hot. Jen is a very pretty blonde, her soft hair falling just past her shoulders. Her breasts are small, but they're perfectly formed, and even after 2 kids her stomach is flat and sexy, and her behind is tight. Her legs are her best feature, which are long and shapely. Even before Ralph and his wife broke up I'd often catch Ralph looking at Jen, so it didn't surprise me that Jen often caught him checking her out, especially since they were spending so much time together.

Ralph and his kids often came over for dinner. One night we were sitting around watching TV in the family room. The kids were downstairs playing in the basement. At my urging, Jen wore a turtleneck, short skirt and tights. Everything was black, which really highlighted her natural blonde hair. She looked incredibly hot.

We sat on the sofa while Ralph sat across from us. Jen was snuggled into me, and her skirt had ridden up, exposing her shapely legs. I saw Ralph stealing glances at her legs, which excited me. Trying to kick things up a bit, I playfully tickled Jen. She laughed and tickled back, and soon we were laughing and wrestling on the sofa. In the process, Jen's skirt rode up even higher, to just below the soft swell of her shapely ass. Jen must have realized that she was about to flash herself to Ralph. She tried to pull her skirt down but I held her firm. "Michael, stop," she pleaded, still laughing.

"Why?" I teased. "Your legs are fantastic, all your skirts should be this short." I looked over at Ralph, grinning. "Don't you think so?"

Jen looked over too. Ralph couldn't seem to take his eyes off Jen's skirt, bunched dangerously high, and her long shapely legs. Long moments passed. Without taking his eyes off my wife's exposed legs, Ralph finally said, "Yeah, she has incredible legs." I sensed Jen blush.

I laughed to try to break the awkward moment. "So, you think Jen should wear shorter skirts, too?"

Ralph's eyes traveled along her long legs. I felt Jen almost shudder under his gaze, and my cock throbbed. Finally Ralph grinned. "Definitely."

Jen finally managed to pull away from me. She pulled her skirt down and walked to the kitchen. "You're both crazy," she said as she returned with another bottle of wine.

We had great sex that night. "Ralph was so hot for you," I hissed as I fucked her. "He couldn't take his eyes off you. He's probably masturbating right now, thinking of running his hands over your legs, of fucking you." Jen didn't say anything, but she was definitely more turn-on than usual.

I encouraged Jen to buy shorter skirts, and wear them more often. One day while shopping I pointed out a mini-skirt displayed on a manikin. "Ralph would love to see you in that, don't you think?"

"Just stop," she said laughing.

"Come on, you should buy it for your boyfriend."

Jen jabbed me in the ribs. "You jerk, he's not my boyfriend."

"Okay, then your lover."

"You know he's not my lover."

"Maybe not yet. But you're hot for each other. It's only a matter of time."

Jen shook her head. "Whatever." But she found her size and modeled it in front of a mirror. It fell a few inches above her knees.

"It's short," she said. Most of Jen's skirts were knee length. This one was shorter than any Jen owned.

"You should buy it. Your boyfriend said he wanted to see you in shorter skirts."

Jen scowled at me, but she bought the skirt.

I couldn't help teasing her as we left the store. "I thought you said he's not your boyfriend."

"I bought it to wear for you, not Ralph."

But I hoped otherwise. Ralph really was like her boyfriend. Because of the kids, they spent a lot of time together, often without me. Ralph worked from home and had a flexible schedule, so they often saw each other during the day. They were becoming better and better friends, and enjoyed each other's company. It was clear they were physically attracted to each other. Given the right situation, I was sure they would wind up in bed. At least, that's what I hoped.

Jen wore her new mini-skirt that weekend. We took Ralph to dinner to celebrate his birthday. Along with the mini-skirt she wore a sheer white blouse. Underneath she wore matching lacy white bra and panties, and off-white hose.

Ralph's eyes practically popped out of his head when he saw Jen. It was probably the shortest skirt she had ever worn. With her high heels, her slim legs seemed to go on and on forever.

Ralph was riveted to Jen all night, and she loved the attention. I did everything I could to encourage their flirting. I made sure their drinks were continually re-filled, and made every excuse to leave them alone. Seeing them together got me so hot. As the evening progressed, aided by drinks, they edged closer to each other in the booth, their faces almost touched as they flirted and laughed. Looking at them, you'd think Jen was with Ralph, not me.

As I returned with a new round of drinks Jen broke away from Ralph, looking a little guilty. "Let's dance," she said to me as she grabbed my hand.

"Not me, I'm too tired." I motioned Jen's hand to Ralph. "Ralph, do me a favor and dance with my wife, and let me sit here and enjoy my drink."

Ralph didn't hesitate to jump up and take Jen's hand. As he lead her to the dance floor, Jen looked back at me and playfully stuck her tongue at me.

The DJ was playing fast songs. As soon as I could, I headed over to the DJ and gave him $20 to play a set of slow songs. Jen and Ralph had disappeared in the crowd. I searched through the club and found them just as the first slow song began. The dance floor was crowded enough that I was able to watch without being seen.

Jen didn't seem to know what to do when the slow song began. Ralph whispered something in her ear. Maybe it was a joke, because Jen laughed. That seemed to break the ice, because Jen took Ralph's hands when he offered them to her. At first they were holding hands, dancing and talking. Gradually, Ralph pulled her closer to him, until eventually he had his arms around her.

I was so hard it hurt. Watching Ralph press his body against my wife was incredibly thrilling. As they swayed to the slow music, Ralph began to lightly caress Jen's back, rolling her soft blonde hand in his fingers, then trailing his fingers down her back to just above her behind.

At first they continued to talk as Ralph did this, his movements done almost absentmindedly. But it seemed Jen was having a harder and harder time to continue the conversation. Maybe she had had too much to drink? Maybe she was getting too turned on? (This is what I hoped.) Eventually Jen gave up talking and rested her cheek against Ralph's chest.

Ralph used this as an opportunity to wrap his arms around Jen. His caresses continued, but now his hand was caressing her side. I'm sure his fingers were running along the side of her breasts, feeling the lace of her demi-bra. At first Jen tensed, but as the music continued she relaxed and let Ralph touch her. Ralph's caresses were so subtle to be non-threatening. Yet, he was almost cupping her breasts. My heart was pounding in my chest. If I watched much more I was going to cum in my pants.

The set ended, causing Jen and Ralph to part and awkwardly look at each other. Jen smiled and kissed Ralph on the cheek — thanking him for the dance? — and headed back to our table. I quickly made my way back to the table, and pretended like I had been there the whole time.

That night we fucked like rabbits. The next morning we took our time, yet our lovemaking was just as exciting.

"I watched him touch you," I said as we slowly fucked. "I watched him fondle you."

"I'm sorry," Jen said alarmed. "I --"

I cut off her apology with a kiss. "I'm not mad. It turned me on."

"It excited you?" Jen hesitantly asked. "To see Ralph touching me?"

"Oh god, yes! I was so hard it hurt."

"I think I was drunk. I think Ralph was too."

I kissed Jen again. "I told you I wasn't mad, so you don't need to make up excuses. I saw how turned on you were. Anyway, I paid the DJ to pay slow songs. I was hoping Ralph would hit on you."

"You're joking?" Jen asked, her tone serious.

"Does that really surprise you?"

"No — I guess not," she said softly.

"I wish it had gone farther."


"I wish he had taken you to a store room — or the car — and fucked you."

"You're not serious."

"He probably hasn't had any since Lynn left him. He's so horny he's probably going crazy." I smiled, a twinkle in my eye. "If you're really his friend you'd give him a mercy fuck."

Jen tried to scowl, but we were both close to cumming. "You're crazy," she managed to say between heavy breaths. We both came, almost at the same time.

We were silent for long moments, both of us catching our breaths. "If it ever happened, I wouldn't be mad," I said, breaking the silence. "I'd be okay with it if you slept with Ralph."

Jen didn't answer. Instead, she kissed me and fondled my balls, and we began another round of lovemaking.

Chapter 2

It happened about a month later.

I was going on a business trip. "You and the kids should hang out at Ralph's house," I encouraged Jen before leaving. "It'll be easier for you. The kids can play with Ralph's kids, giving you a chance to relax."

It worked better than I hoped. I was gone 4 nights. Jen and Ralph were together 3 nights, twice at his place, and once at ours. I was in a constant state of arousal, wondering and hoping about what might be happening.

I got home late Friday night. The kids were already in bed. I found Jen in the family room. She was dressed simply, with jeans and an untucked button down shirt. Her hair was pulled back, and she didn't have any makeup on. She looked great. With her hair pulled back, and without makeup, she looked like a coed.

She looked nervous, and I could tell she wanted to talk. As soon as I sat down she took my hands in hers. "I need to tell you something," she began hesitantly. "I think you'll like what I'm about to say."

She took a deep breath, and looked like she was building up her courage. I didn't say anything. I started getting hard. Was she going to say what I was hoping to hear?

Finally she said, "I slept with Ralph last night."

My throat dried up, and I felt dizzy. I wasn't able to speak. "Oh my god," I thought. "It's finally happened."

Jen misunderstood my silence. Alarmed, she quickly added, "I mean, we didn't sleep together. But ... we had sex."

She looked at me expectantly, fear in her eyes. "Are you mad?"

I took her in my arms, and kissed her. "I love you so much." We started making out. I unbuttoned her shirt and cupped her breasts. She wasn't wearing a bra. I rubbed her nipples the way I knew she liked it. "Tell me what happened. Tell me everything."

Jen told me they were together Tuesday, Wednesday and Thursday nights. After eating dinner — usually pizza — the kids went downstairs to play in the basement, while they stayed upstairs. They had a wonderful time talking and laughing. And the sexual tension, already present, grew the more time they spent together.

Last night, they were having so much fun the time flew by. Before they knew it, it was passed midnight. They went downstairs to gather the kids, but they had fallen asleep on the sofas. With the kids asleep, Ralph asked Jen for a nightcap before he headed home with his kids.

"He'd been flirting with me all night, and I'd been..." Jen hesitated, uncertain of what to say.

"And you were flirting back," I said, completing her sentence.

Jen nodded, her eyes again uncertain.

I kissed her. "You don't have to worry about me being mad." I brought her hands to my crotch, letting her feel how hard I was. "I love what you did."

Jen kissed me. "I love you so much." She unzipped my pants and began stroking my cock.

"I love you too. Tell me what happened next."

"We were sitting on the sofa, sipping wine. Then we both stopped talking. It was one of those awkward silences. Then Ralph took my wine glass away, and he put his down on the table too, and then he — well — he kissed me."

"Did you try to push him away?"

"Well, I — no, I guess I didn't," she replied honestly. "After the last few months, it felt — well — natural, or inevitable, or something like that."

Things happened really fast after that. Ralph fondled her over her clothes, cupping her tits and rubbing her nipples. His hands explored her body, caressing her long legs. She didn't stop him when he reached under her skirt. She was soaking by that time. He brought her to her first orgasm with his hand. Then he buttoned her blouse and unsnapped her bra. She was soon writhing under him as he sucked and rubbed her nipples. He reached behind her and unzipped her skirt, and in one motion pulled it and her panties and hose off. She was nude, except for her blouse and bra which were open and hanging loosely off her shoulders. She was completely exposed to him.

Ralph unzipped his pants and took out his hard cock. He pulled Jen to the edge of the sofa, putting her slim legs over his shoulders. With his hand he guided his cock to her pussy lips, and then began to slowly push into her.

I felt lightheaded as Jen spoke. "Was he big?" I asked.

"Yeah," Jen said, still stroking me.

"Bigger than me?"

She nodded.

"How much bigger?"

Holding my penis in one hand, she motioned with her other. "About this much longer," she said, holding her other hand about 5 inches past the tip of my cock. "And about this thick." She circled my penis with her hands. The circle was about as wide around as her wrist. My cock twitched as she told me this.

"So, he was twice as big as me?"

Jen nodded.

"Say it. I want to hear you say it."

"Ralph is huge. He's about twice as big as you."

My cock twitched again. I was so close to cumming.

"Did it feel good? Getting fucked by that big cock?"

"Yeah. I mean, it took a while to get use to, but it felt good."

"Did he make you cum? I mean, when he fucked you?"

"Yeah. I think I may have cum twice. Or maybe it was just one long orgasm."

"Where did Ralph cum?"


"Where did he cum? Inside you? In your mouth? On your tits?"

Jen grew alarmed. "Oh my god, I didn't think of that!"

"Where did he cum?" I asked again. I had had a vasectomy after our last child, and Jen wasn't on the pill.

"Oh my god. Michael, it all just happened..."


"Oh god. I wasn't thinking ... Ralph came inside me."

I couldn't hold off any longer. My cock jerked and I came on Jen's hand.

Chapter 3

The next day Jen cried. Reality set in, and she felt remorse for cheating on me.

"You weren't cheating on me," I assured her. "Don't you understand, this is what I wanted? I wanted you to have sex with Ralph."

After hours of reassurances, I finally convinced Jen that I was okay with it all. That night we made love. She felt different. I'm not big in that department, but usually Jen fits me live a glove. This time she felt loose, even a day after being with Ralph. Even though I didn't feel as much while fucking her, I still came quickly. Her looseness was stark evidence of her being fucked by Ralph's big cock, and it made me so excited.

I wanted Ralph to fuck Jen again. It was like a drug, and I was addicted. But Jen didn't want that. Despite her attraction to Ralph, she wanted a normal, monogamous lifestyle.

But things had changed in our relationship. We saw Ralph just as much, if not more. When we went out as a threesome, Jen often paid as much attention to Ralph as me, if not more. If you saw us together, you'd probably think Jen was with Ralph, not me.

Ralph and I never talked about his relationship with my wife. I think he knew I knew. Maybe Jen told him about my fantasies. We remained friends, if somewhat awkward ones. It was like a don't ask / don't tell relationship.

About a month later, we took Ralph to dinner to celebrate his new job. We sat in a booth, with Jen between us, and as it often happened, Jen had edged closer to Ralph during the course of the evening. Seeing Ralph flirt with my wife never failed to get me hard.

"I'm excited about the new job," Ralph said, "but I have to get a date for the company Christmas party. It's considered bad form to go solo. The problem is, I don't know any girls I'd want to take. I need to take a girl who's pretty and charming — I know it's a terrible thing to say, but my company is like that — and I don't know any single girls like that."

Jen and Ralph talked about single girls they knew, but none of them seemed to fit the bill.

"I have an idea," I finally said.

Jen and Ralph looked at me expectantly. I looked at Ralph. "Why don't you take Jen?"

"What?" Jen asked.

"This works," I said smiling. "You're certainly beautiful and charming, so you fit the bill. No one knows you at Ralph's company, so you can pretend you're single."

Jen knew what I was up to, and scowled at me. "You're crazy."

But Ralph took to the idea. "I think it's a great idea. Michael's right, you're perfect. No one knows you at my new company, so no one will know you're married."

Jen shook her head. "You're both crazy."

It took another hour of convincing, but finally Jen agreed.

Two weeks later, I watched Jen get ready for her date with Ralph. I watched her do her make up and hair, and spray on perfume. I watched her put on her strapless bra, and then roll the sheer black stockings up her legs. Then I watched as she attached the stockings to her garter belt. Jen normally wore tights or pantyhose, but I convinced her to wear a garter belt and stockings. We argued about it for a while, but she eventually agreed.

Then she slipped on her high heels. They were new, I bought them as a Christmas present. Jen was thrilled to have them, as she always wanted to own Jimmy Choos, but she was less than thrilled knowing I had bought them for her date with another man. Still, she looked incredible in them, the 4 inch stiletto heels making her already shapely legs even more incredible.

I watched her step into her strapless black dress — I zipped her up -- and put on lip stick. As I watched her I couldn't believe how lucky I was to be married to such a beautiful, desirable woman. Jen turns heads wherever she goes. She is a true beauty, any man would want her. Despite my excitement, I started wondering if I was making a terrible mistake. Why was I giving my wife to another man? Why would I ever allow another man to touch her incredible body?

But it had gone too far to stop. I was so excited, it was hard to keep from shaking.

The doorbell rang. It was Ralph. We both headed to the stairs when I noticed Jen's left hand. I touched her engagement and wedding rings. "You need to take these off. Remember? You're a single girl tonight."

Jen nodded, although not enthusiastically. She took off her rings and put them on the dresser.

I headed down the stairs and greeted Ralph. I shook his hand, and we made some small talk. Then we both got silent as Jen walked down the stairs a few minutes later. She was incredibly beautiful and desirable.

She said hi to Ralph, and then handed him her wrap. "Could you help me with this?" Ralph gently placed the wrap around Jen's bare shoulders. As he did, Jen looked into my eyes. "Are you sure you want me to do this?" she silently asked me. My only response was to hand Jen her purse. "You wouldn't want to forget this." We both knew what was inside. The condoms I had purchased earlier that week.

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