The Willing Cuckold Ch. 01

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In the mid-1980s I was an engagement manager at a national consulting firm on the path to a partnership so I traveled frequently and worked long hours. Dee was very understanding as she had worked with me as our team’s administrative assistant before she left to go to a large regional law firm.

We had gotten together when Dee showed up at a going away party for another co-worker about a year after she left the firm. I had forgotten how attractive she was, shoulder-length espresso brown hair framing her pretty face, slender athletic figure, and a laugh that filled the room. Throughout the evening, she told me she had broken up with her boyfriend of five years and had moved to a small studio apartment in the city. We kept talking and drinking while we commiserated over being single and celibate until we were the last two people at the bar.

We staggered out of the bar and I hailed a cab. When we got in the cab I gave the driver my address and said we had to drop Dee off first. Before I could turn to ask Dee for her address she told the driver, “Just one-stop” and clasped my hand in hers.

When we entered my condo Dee said she had to use the bathroom so I directed her to the guest bathroom and I went to clean up in my bathroom. After I had relieved myself and brushed my teeth I came out of my bedroom to find Dee. Before I reached the hallway I heard the shower in the guest bathroom turn off. When I turned the corner Dee walked out of the guest bathroom with a towel wrapped around her hair, and nothing else. She walked into the well-lit hallway and she was physical perfection, 5’5″, 120 lbs, pert upturned 34A breasts, long toned legs, and a lovely bronze skin tone that came with her Mexican heritage.

Dee walked up to me and tilting her head up (I am 5’10”) gave me a passionate kiss. She then dropped to her knees, unbuckled my belt, and unzipped my pants. Dee pulled my pants and boxers down to my knees and started stroking my cock. After a few strokes, she engulfed my cock in her warm wet mouth. She licked around the head of my cock and then started slowly pushing my cock deeper into her mouth. I could feel the head of my cock being squeezed against the back of her throat as she wrapped her hands around my ass and pulled me closer to her. Dee slid her tongue under my cock and kept bobbing her head until my cock slipped into her throat. The warmth and firm pressure of her throat coupled with the sight of her beautiful breasts pushed me to a quick orgasm and I pumped my semen down her throat. Dee sucked on the head of my cock to get every last drop of cum.

I pulled Dee up and led her into my bedroom. I pushed her onto my bed and removed the last of my clothes. I pushed Dee’s legs apart and started kissing her thighs. I worked my way up her thighs to her crotch and peeling her labia apart started lapping the furrow between her legs. By this time Dee was dripping wet. I licked the inside of her pussy lips and then furled my tongue into a point and started exploring her vaginal canal with my tongue. Dee started to moan and writhe as I tongue fucked her. I stopped briefly to wet my index finger so I could explore her anus while I tongue fucked her. I could feel my finger putting pressure against my tongue as it plunged in and out of her ass. Dee went rigid for a second and then her body shuddered as she climaxed. Her sphincter clamped tightly on my finger and her vagina squirted fluid onto my tongue. Dee pulled me up and kissed me gently as she wrapped her arms around me. We fell asleep still embracing.

Dee was sucking on my cock and gently stroking my thigh were her nails when I woke up. When she sensed I was awake she started sucking more vigorously until I was rock hard. Satisfied with her handiwork she straddled my body and guided my rock-hard cock into her waiting pussy. She started rocking back and forth making sure her clit had maximum contact with my pelvis while my cock slid in and out of her pussy. Dee started breathing faster as she rocked back and forth until she came to a complete stop and collapsed on top of me. After a couple of minutes, she started moving again, slower this time, as she kept riding my still hard cock until I climaxed and shot my load deep into her pussy.

We lay in bed and joked about the end of our sexual drought. We kept hugging as if we could not believe we had found one another. To our pleasant surprise, we worked well as a couple. We enjoyed each other’s company and were happily compatible, physically and emotionally. I worked long hours and traveled and she was independent and liked going out dancing by herself and with girlfriends. But when I was available we spent the time together, going out to eat, going to bars, movies, seeing friends, the stuff most couples do, just not as frequently as most couples.

After about six months of dating, Dee’s older sister Dani invited Dee to go with Dani and her best friend Mary for a 3 day weekend in Cabo San Lucas. I could tell Dee wanted to go but didn’t eryaman eve gelen escort want to spend the money. I had to work on a major system conversion at a client over the entire weekend so I encouraged Dee to go by paying for her plane fare and her share of the hotel. Dee was excited and bought a couple of bikinis and a short flirty sundress for the trip. On the appointed day I dropped Dee off at the airport on Friday afternoon and drove out to the client’s offices to spend the next three days monitoring the conversion.

Dee’s flight returned early Monday evening and I was at the gate (this was in the ’80s) when the flight arrived. Dee, Dani, and Mary came out of the gate door, tanned and glamorous. Dee and Mary were a little buzzed from the cocktails they enjoyed on the plane. The three ladies laughed and joked as they walked to baggage claim. After collecting their bags, Dee, Dani, and Mary hugged and said their farewells. The entire time Dee had not said a word to me. On the way to the car I tried to make small talk with Dee but she was remote and only responded with a yes or no. On the drive into town, Dee looked out the window and didn’t talk. Thinking I had unknowingly pissed her off I didn’t try to engage her in conversation knowing she would say something when she was ready.

Finally, Dee said, “I met somebody in Cabo.”

When I heard that it felt like my stomach dropped to my feet and my heart started beating faster. I had no idea what to say to that so I did not say anything.

“He was the DJ at the bar we went to Friday night. Roberto” she continued. “When we went back Saturday night he was there with a couple of friends but he wasn’t working that night. They bought us a round of tequila shots and asked us to dance. We kept dancing and drinking shots with Roberto and his friends until they decided they wanted to go to a club at a resort on the other side of town. The six of us couldn’t fit in one car so Dani and Mary went with Roberto’s friends in their car and I went with Roberto in his car.” Dee paused and took a deep breath before she continued, “Somewhere along the way Roberto pulled off the road into a little grove of trees. He grabbed me and started kissing me, and, and I kissed him back. He was good-looking and charming and I was pretty drunk. We kept kissing and before I knew it he had unzipped my dress and pulled it down to my waist. Roberto started playing with my nipples and telling me how beautiful and sexy I am and how he loved my breasts and nipples.”

Dee’s explicit description of events made me uncomfortable and excited at the same time. The jealousy I felt was overwhelmed by the incredible sexual arousal I got from Dee’s description of the night’s events.

“Roberto started sucking on my nipples as his hand started inching towards my pussy. I told Roberto I was having my period but I wanted to suck his cock. Roberto leaned back in his seat and pulled his pants down to his knees and offered me his semi-hard cock. By this time I was so horny, I almost inhaled that fat cock of his. Roberto put his hand on the back of my head and pushed my head down until his cock was deep in my throat and my lips were touching his balls. He must have been super horny because he came quickly.”

Did you swallow his cum?” I asked.

“Of course. But I don’t know if I swallowed his cum as much as he shot it down my throat. You know me, I prefer to not taste the cum so I want a guy to cum while his cock is in my throat. As soon as he finished cumming he pulled his pants up and started driving to the club at the resort.”

“And?” I asked.

“And that was it. We danced at the club and then they drove us back to our hotel. Roberto had to work Sunday night. We went to his club Sunday and danced but that was it. I’m sorry. I was stupid. Drunk and stupid. I don’t want to lie to you and I don’t want to lose you.”

“Okay.”

“Okay what? Okay, you think I am a piece of shit and you don’t want to see me anymore? Or okay we can get through this?” Dee asked meekly as if she was afraid to hear the answer.

“Okay, I should be a better boyfriend and spend more time with my girlfriend and less time at work. Okay, I should have been with you in Cabo and not spent the last 72 hours working on my client’s system conversion. And okay, it’s messed up but I am incredibly turned on by imagining you blowing another guy. Like you’re a porn star and you’re performing for me.”

Dee teared up and put her head on my shoulder. “If you forgive me I’ll be your porn star anytime. I’ll do anything for you.”

We went back to my apartment and had the most intense combination of make-up sex and submissive/dominant fucking. Dee meant it when she said she would do anything, she swallowed my cock before lubing up my cock and asking me to fuck her ass. I was happy to oblige my little slut and took the bottle of lube from her and squirted some into her anus before I started pushing my cock against her bala escort little brown pucker. Dee moaned a little when my cock pushed past the tight muscles of her asshole into her anus. I stopped before slowly inching my cock past her inner sphincter and into her rectum.

I kept adding more lube to my cock as it continued its passage into her rectum. I slowly rocked my cock back and forth in her ass and told her how I thought she is so beautiful and sexy I could understand why other men would try and seduce her. When she heard that she started bucking her ass backward trying to make my cock go as deep into her ass as possible. My balls were banging against her pussy when I started spurting my cum into her warm tight ass. When she felt my cock spasming Dee reached down between her legs and started rubbing her clit while she clenched her ass tightly around my cock. As I was finishing Dee stiffened and stopped moving as an orgasm swept over her body. We both stayed stock still for a few moments before we both fell forward, my cock still embedded in her ass.

“I would do anything for you,” Dee whispered to me. “Anything.”

Our relationship was strengthened by Dee’s confession. After her trip to Cabo, we both felt we could talk about anything together. It is liberating to get past something like infidelity. It allowed us to talk about how she felt neglected at times because I worked so much. Dee said no matter how much she rationalized my dedication to my job, at times she felt like I was not attracted to her. She talked about how having blown Roberto was all about the excitement she felt when a stranger desired her. Dee also explained that she could separate sex from emotion. Dee thought of it as a strictly physical act, like dancing, when she was with a stranger but it was intimate and an expression of love when she was with me. Dee recognized that I was the monogamous type and she appreciated my devotion to her. Having talked it out neither one of us thought we needed to do or say anything more.

Dee started having drinks after work with a friend from work, Monica. Monica was married with a young son but according to Dee, she was bored with her husband, Tom. Monica had movie-star beauty, a beautiful face, wavy jet black hair, large breasts, a nice round ass, and was ready to party. While I was on a business trip Dee made plans to go dancing with Monica after work.

When I returned Dee and I went to our favorite restaurant for dinner and cocktails. Dee shared details of her night out with Monica. They had started out drinking at their usual bar next to their office building. Pretty soon two guys introduced themselves and offered to buy Dee and Monica a drink. The women didn’t hesitate and accepted their offer. The two guys sat down with them and they talked and drank for another hour or so. Finally, Dee thanked them for the drinks and said they had to leave to go dancing. The two guys immediately asked if they could go dancing with them and Monica accepted on their behalf.

Dee said they went to a popular nightclub in the commercial area of town and had a fun time dancing. Finally, Monica said she had to go home so they thanked the guys and shared a cab home. During the cab ride Monica told Dee one of the guys, Pete, asked for her number and told her he and Dave (the other guy)wanted to know if they wanted to go dancing next week. Dee asked Monica what she told him. “I gave him your phone number and told him we would love to meet up with them next week,” Dee told Monica she could not commit to anything without talking to me about it.

“Do you want to go out with them next week?” I asked.

Dee hesitated and then said, “If you wouldn’t be upset, yes, I would like to go dancing with them again. It was fun, they’re fun. And Monica wants to see Pete again, she likes him.”

“Then I have no objections. I am in town all next week so when you go out with them maybe I’ll take the opportunity to have dinner with my parents.” With that, we moved on to other topics of interest.

The same night she made plans to go dancing with Monica and the two guys I made plans to have dinner with my parents. I returned from dinner before 9 and was asleep by 11. Dee woke me up around 1 am by stroking my cock and covering my face in kisses. Once my cock was fully erect she bent down and started sucking my cock but didn’t take it down her throat. She stopped sucking long enough to say, “I am so horny don’t come in my mouth. You have to fuck me and let me cum.” and resumed sucking my cock. It did not take long to guide my cock into her very wet pussy. She pushed down and took my entire cock into her vagina in one stroke. “God, I am so horny. Dave tried to get me to fuck him.” Dee said through clenched teeth. “Pete and Monica were in the backseat of the car and they were fucking. Monica was moaning and I could hear Pete’s cock making squishing noises in her pussy as he fucked her Honey it was the first time I smelled another woman’s pussy. etimesgut escort I thought it was so sexy!”

You liked the smell of Monica’s pussy?” I prodded her.

“Yeah, I thought it was so sexy knowing she was fucking Pete in the backseat. Dave kissed me and felt my boobs but I didn’t let him touch my pussy. Dave even pulled out his cock and asked me to suck him but I said no. He has a nice thick cock and I wanted to put it in my mouth but I couldn’t do it to you again. Monica let Pete cum in her mouth so she wouldn’t be dripping his cum when she got home.”

Dee resumed humping my cock with abandon until she leaned forward and pushed back as far as she could. Dee shuddered as her orgasm swept over her body. Her pussy involuntarily clamped down on my cock and I started spurting cum into her hot channel.

“Dee, I would not be upset if you fuck Dave as long as you tell me about it afterward. The thought of him fucking you excites me. I would like to fuck you when you have another man’s cum in your pussy.” I confessed.

“Oh honey, I don’t know if I want to do it. I mean tonight I wanted to do it but I could not bring myself to do anything with him. Let’s not talk about it tonight. Just hold me and tell me you love me.” And with that Dee quickly fell asleep. Sleep did not come as quickly for me. My mind was racing with images of beautiful Monica getting fucked in the backseat of the car with her big tits flopping around and her pussy pumping out gobs of her fragrant pussy juice on her date’s cock. My cock got rock hard again as I imagined it was Dee getting fucked in the backseat of a car. My mind was made, I wanted Dee to go out with Dave again and fuck him.

The following week I was working in the Midwest at a client all week. On Tuesday night Dee called me to check in and see how I was dealing with the snowstorm that had descended on the region in which the client’s office was located. As we talked about the snow and the progress of our engagement Dee suddenly interjected, “Dave and Pete want to go out Thursday night. They invited us to dinner at Pete’s apartment.”

I thought for a second and said, “That sounds like fun. What did Monica say? Isn’t Tom getting suspicious?”

“Monica told him I want her to go with me to have dinner with my mom and Diana (Dee’s younger sister). She wants to go to Pete’s.”

“You should go then,” I said.

“She wants to fuck Pete again. Dave is probably hoping I will fuck him this time. And I don’t know how good I will be if I am put in that situation again. I remember what you said last week but I don’t want to take a chance I will screw up our relationship. I think I just answered myself, “I don’t want to go.”

“Dee, I want you to do whatever you want. I don’t want you to feel you’re in a cage, the door is always open. And I am going to love you whatever you decide. As long as you don’t keep any secrets from me.”

“This is why I love you so much,” Dee responded. “I don’t know, I want to think about this some more. I’ll talk to you later.”

Dee called me the next day to tell me she told Monica to tell Pete and Dave she would join them for dinner. “I don’t think I want anything to happen tomorrow night, but I promise you if anything does happen I will tell you,” I told Dee we were leaving late Thursday night in case the storm shut down the airport on Friday. With any luck, I would be home around midnight.

After a bumpy flight home, I did get home a little past midnight. After eating a bowl of cereal and taking a nice hot shower I collapsed into my bed and fell asleep. When I woke up Dee was in bed with me and it was time to get ready for work. With some prodding from me, I got her up and in the shower while I went to make coffee and toast for us. By the time Dee was dressed and had applied her makeup, she had to leave to catch the bus. She gave me a quick kiss and shot out the door. Her casual manner made me think nothing happened the night before so I got dressed and headed into the office. As soon as I walked into the office I was dragged into a series of meetings that lasted all day. Late in the afternoon, my secretary slipped me a note saying Dee had called a couple of times, and when I did not return her calls she asked my secretary to ask me to meet her at our favorite restaurant at 7 pm.

When I walked into the restaurant I spied Dee sitting at the end of the bar chatting amiably with our friend Kevin, the bartender. Dee looked like a model out of Vogue, her makeup lightly and artfully applied, she was wearing her espresso brown hair down to her shoulders. She wore a tan suede jacket over a cashmere turtleneck sweater, skinny jeans, and her favorite brown loafers. As soon as she saw me she jumped up, kissed me, and embraced me with a warm hug. The first words out of her mouth were, “I love you so much! You are the best boyfriend in the world.”

That got my antennae vibrating. “I love you too Dee. What did I do to deserve such praise? I was just about to apologize to you for not being able to return your calls today.” Just then Kevin brought me a beer and a glass of wine for Dee. We took the opportunity to order bar burgers, an order of Buffalo Wings to share, and another round of drinks to back up the ones we had.

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