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Fifty-Year-Old Woman's First Time With A Woman

"I helped a sexy MILF cross to the bi-sexual exhibition side of life"

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On a lazy spring day in New York, I decided to have lunch with a sexy woman named Suzanne that I had been trying to get into bed for years. She knew it too. I was always very direct when asking her and she would blow me off like I was a child.

Until today. We had a great lunch and too much wine and I started teasing her about how she always stiff-armed me.

I said, “How about we just have oral sex? I like to think I'm pretty good at eating pussy and I bet you're good at sucking cock. Blow jobs don’t count as having sex – Bill Clinton did it and all the teenagers think blow jobs are not sex.

She said, “You're right. I give superb blow jobs and I've been swallowing since college. Do you think I could go home to Richard and tell him I had a guy's cock in my mouth and swallowed his jism and that doesn't count as having sex?”

I said, “What if I don't cum in your mouth?”

“Awww poor boy, where would you like to cum, on my tits, my ass, my pussy, or my face?” she asked.

She continued, “I love getting facials, it's soooo good for the skin and your balls get emptied too.”

Before I could answer she coyly looked at me and said, “Look we’re both married and it wouldn't be right. However, I'm going to be fifty soon and want to try being with a woman once for my birthday. I wouldn't consider that cheating and if you could arrange it. Then, maybe you could be in the same room and you can do to yourself whatever it is that guys do while two women are having sex. Maybe then, I'll let you join in and put your cock in my mouth. I talked to Richard about it, and he was okay with it, but, I don't think he thought there would be a guy in the room too. It can be our little secret you won't tell him, will you?”  

Oh my God, I thought and then BOING, I got a huge hard-on. I think she realized what she had done and said, “Don't worry, that's good exercise for your manhood. Is he very hard?”

I showed her the tent in my pants.

“Hmmmmmm, I bet he would love to fuck my pussy and cum in my mouth right now,” she purred and patted the bulge in my pants.

“Oh poor Jim, are your big balls blue now?”

She was a masterful tease. I excused myself to go to the men's room and jerked off in a stall. I went back to the table with a drop of cum on my business card and put it down in front of her.

“Is that what I think it is?” she asked.

I nodded yes so she scooped it up with her index finger and put it on her tongue and swallowed it.

“Yummy cummy, see I tasted your cum,” she said. ”I love the taste of cum and I hope that wasn't your whole load.”

I assured her it wasn't, “I splooged a ton.”

She said, “Great. I got you aroused and that's how I like it.”

I was starting to get hard again and she knew it.

“Well the only way you will get more of your yummy cum in my mouth is if you can find a woman I can have sex with,” she said. 

Can this be happening I thought to myself.

We continued to talk if I knew anyone that might want to help her fulfill her fantasy. I thought about it and then it came to me – Gail. She's the wife of a friend that my wife and I used to swing with. She and my wife used to put on quite the erotic show for me and her husband, so I know she likes pussy and likes to 69 with a woman. She also has an awesome body, with a thin waist and a set of huge tits.

Gail and I stayed lovers after the swapping ended and I thought she would be up for it. I told Suzanne that I might know someone that she might like and she had an awesome body to boot.

“Hmmmmmm,” she said.

I told her about the wife swapping, strip poker, daisy chaining, and cheating and she was very interested. She said, “Sounds like you and your wife had a lot of great sex, and Gail sounds like a woman who would go for that so let's go for it. I think I want to be with a woman with large tits and a sensuous body. Is she very bushy down there?”

I said, “She used to be and she loves rimming and is very nimble at tribbing.”

“Tribbing?” she queried.

“It’s where two women grind their cunts together in a wishbone position until they cum. It’s very erotic for guys to watch. I've watched her trib with my wife many times and would love to watch you two grinding your cunts together while taking full frontal shots with my phone. Here let me show you some nude pics of Gayle and my wife that no one has ever seen.”

I flipped thru my phone and found two hot pics from back in the day.

She looked shocked and embarrassed and then said, “Is this them doing sixty-nine, and you and her husband fucking them at the same time?”

I nodded yes and said, “The only thing the girls didn’t like was the fact that our balls were always in their eyes and nose while they were trying to focus on eating pussy.” 

She said, “Looks like a great position, and you and her husband seem pretty happy. The one picture of them tribbing looks hot. Now I'm incredibly horny.”

As we left the café I couldn't keep my hard on down and she noticed.

She looked down and said, “Down boy – he will cum soon enough,” and gave me a come hither look like it would happen soon.

Oh my fucking God. I was ready to cum in my pants. Suzanne asked me to call Gail to see if it would be fine with her. I said I would do it right away. Oh yeah, I thought.

I called Gail and asked her to dinner. We talked about Suzanne and the situation and she asked about Suzanne’s body. I told her she was very pretty, about 5’4” with 34C cup tits and a thin waist, and a nice ass.

Gail asked, “Is her pussy hairy?”

I said, “I don't know.”

She said, “You don't know? You’ve never seen her naked? So you have never fucked her?”

I said, “No.”

Gail said, “Oh, you poor, poor man. Then you do need me to see her nude and have sex with her.”

“Yes,” I said sheepishly.

Gail then said, “Make it happen. I think you will enjoy the show and you probably will even join in. I won’t have a problem with that. I’ll even add some twists you haven’t seen.”

She then said, “Let's get in your car and I'll give you a preview of what’s to cum,” with an emphasis on the word “cum”.

We got in the backseat of my Escalade and she stripped nude in seconds. I got the hint and did the same. My cock was huge and hard as a rock.

Gail said, “I was always impressed with your ability to get hard immediately, not many guys can do that, and it takes hubby a while.”

She then began to stroke me and then put me in her mouth and sucked me up to my balls.

“Cum in my mouth, Girthman, give me all your jism,” she said.

I then got the greatest blowjob of my life. This girl always knew how to suck cock. Gail sat up and licked her lips and then said, “Let's do this as soon as possible, it sounds like fun. Now, eat me cunt-lapper, and make me cum. I still need to get off.”

Oh yeah as I went down on her and gave her the orgasm of a lifetime. I was in heaven.

I went home and called Suzanne and told her that Gail was looking forward to “meeting” her.

Suzanne seemed eager and said, “I'm so horny right now, I'd even fuck you.”

“That would be great but Gail just gave me a great blow job. You're going to like her she's great with her mouth,” I said.

Suzanne said, “I like to think I'm pretty good too, let's see who sucks a better cock.”

I was ready to burst which meant she was going to blow me too.  We agreed to meet at the Oyster Point Hotel on the Jersey Shore on Friday.

I got there at noon and texted the girls to meet me in the bar. I sat at the bar and ordered some wine. Gail showed up and came over and gave me a long kiss and sat down and ordered some wine too. Suzanne showed up and kissed me and Gail on the cheek and sat on the other side of me and ordered a dirty martini.

The bartender looked more than a little intrigued. The girls looked like they liked each other and we all clinked our glasses.

I said, “Bottoms up,” and patted both their asses.

Gail said maybe we should say, “Down the snatch,” which we all laughed at.

The bartender giggled while pretending not to hear. They finished their drinks and ordered another.

I said, “Why don't you give each other a kiss on the lips to get acquainted.”

They both leaned over me and kissed for about five seconds and then sat up and smiled. That was good they both said.

I said, “I think it will be better if you two were naked,” which they both agreed to. “One more drink and it's off to the room to get naked,” I said.

They both excused themselves to go to the lady's room. The bartender, who had overheard a lot of the conversation and witnessed the kissing came over to me and said, “You are one lucky guy. They are both smoking hot.”

I said, “We’ll see. This is going to be their first time together and my first time with the brunette,” to which he responded, “Hmmmmmm, if you need a fourth I'm available,” he said half-jokingly.

I just nodded. The girls returned holding hands which was a good sign and told me they kissed again in the bathroom and felt each other up. BOING. Suzanne and Gail noticed the tent in my pants.

Gail said, “Mr. Happy looks like he's ready to bust out,” and Suzanne nodded and gave me a sly look and winked. They finished their drinks and ordered a round to go and we headed up to the room.

I turned to see the bartender giving me a thumbs up and I responded by lowering my hands to grab their cute asses. Suzanne didn't flinch and winked again which was a good sign. We got in the elevator and they hugged each other and kissed like crazy. Another good sign.

I was feeling really good about this. Really good.

We got to the room and I opened the door and walked in.  It was a suite with a couch, a sitting area, and a king-size bed, with a wall of mirrors on one side. Perfect. The girls were impressed.

They both turned to me and told me to strip to my undies.

Gail said, “We talked about it in the bathroom and figured you should get nude first so we could have fun teasing your big hard rigid cock.”

I thought this wasn't a bad thing and stripped down to my thong in less than a minute.

Suzanne looked at my bulge and said, “Hmmmmmmm.”

Gail began to rub my cock till it got really hard.

She looked at Suzanne and said, “You haven't seen his cock yet, right?”

Suzanne said, “No, I haven’t had the pleasure,” as she giggled. 

Gail said, “Then this is your lucky day, but not quite yet.  Why don't you rub him to keep him hard.”

Suzanne gently rubbed my cock and purred. She then slipped her hand into my undies and grabbed my cock. “Oh fuck, he's so thick.” She said.

“I told you about his girth, but don't peek yet,” Gail said.

Gail told me to stand against the wall of mirrors and put my hands behind my back. I complied. She then went to her purse and got out a blindfold and handcuffs which she then put on me and the blindfold around my neck.

“Don't worry, I'll give you a peek now and then,” she said.

They then faced each other and began an awesome display of French kissing while groping each other's bodies. Gail slowly unbuttoned Suzanne's blouse and removed it, and then unzipped her skirt and took that off too. Suzanne was down to her sexy skimpy undies, thigh highs, and fuck me stiletto heels.

Gail took a step back and admired Suzanne's figure and said, “Very sexy body, I'm going to have fun with you.”

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Gail then put the blindfold over my eyes and ripped my thong down to my ankles. Gail said to Suzanne, “Tada, how do you like that cock?”

Suzanne said, “Oh my god, he's so thick. That is one fat cock.”

Gail said, “He’s so thick I can't close my hand around it, I call him Girthman. Why don't you pull the skin way back and kiss the tip? I’m sure he will love it.”

Suzanne bent over and kissed my knob.

“That’s enough cock kissing. Let's play dominatrix. Now strip you cunt,” she barked as she lowered my blindfold so I could watch.

Suzanne was a bit taken aback but knew what she had to do. She unhooked her bra and revealed two awesome tits with huge nipples that had eraser tip ends. Gail grabbed her tits roughly and pinched her nipples really hard.

Gail said, “Someone looks horny, now turn around and bend over my love bitch.” Suzanne complied.

Gail said, “Now, slowly pull down your panties and spread your ass cheeks,” which she did.

Gail said, “Oh my fucking god your ass is fucking gorgeous and your cunt lips look ripe enough for a fierce tongue lashing.”

WHACK! WHACK! WHACK! WHACK! Gail gave Suzanne four powerful slaps on her ass which took Suzanne back a bit.

Gail dropped to her knees and said, “Now I'm going to rim your truffle tunnel and abuse your snatch lips,” as she dove her tongue up her ass while fingering her clit hard.

“Oh fuck, oh fuck, oh my fucking God,” Suzanne screamed in a good way.

After a few minutes, she had an incredible orgasm. I never saw Gail like this. I guess these were the other tricks she said she was going to show me.

“Okay, stand up my sex slave, and turn around,” she barked.

Suzanne did as she was told.

“You are fucking gorgeous and what a lovely bush. Let me have fun with your pink pearl of love,” Gail said.

She went to her purse and took out some objects. There was a butt plug, nipple clamps, and a fur-lined clit clip.

Suzanne asked, “Is this going to hurt?”

Gayle said, “No, my little sex slave, it's a pleasurable pain. We will all enjoy this.”

She then inserted the butt plug up Suzanne's ass.

“Ooooooooo, fuck me,” she groaned.

“Yes, that’s the sexual objective, and we’re not quite there yet,” Gail said.

She then roughly placed the nipple clamps on her taut nipples and the fur-lined one on her protruding clit.

“Mmmmmm, this feels pretty erotic,” Suzanne growled.

“We’re almost there, cunt. How does she look Jim?” she asked me.

“Pretty subservient and smoking hot,” I said. “Ready for a parade.”

“Precisely what I had in mind,” Gail stated.

Suzanne looked at both of us quizzically and said, “Have you two done this before?”

“Not with you, bitch,” as she chuckled a little

She then attached a small chain to all three clamps and pulled back the window treatments to the sliding doors that faced the bustling hotel patio.

Suzanne saw the patio was full and said, “No, no, you’re not going to do what I think, are you?”

“We’ll see, but you won’t,” Gail said as she got a blindfold and covered Suzanne’s eyes.

“Please, don’t do it. No, no, I’ve never done anything like this,” Suzanne begged.

Gail said, “Then this will be one of many firsts you experience today my little slave cunt.”

She then paraded her around the room pulling the chains harder to make Suzanne catch up. They stopped if front of the sliders and a few patrons noticed.

Gail said, “We have some observers and a few thumbs up.”

Suzanne said, “At least they can’t see my whole face.”

“Now they can,” she said as she removed the blindfold.

“Oh shit, no, no, no,” Suzanne wailed but could not cover up because Gail held the chain high.

“Wave to your fans. Oh, you can’t. Tsk. Tsk. I’ll wave for you,” Gail said as she kissed Suzanne before closing the sliders.

“Wasn’t that erotic, my little exhibitionist?” Gail asked.

Suzanne said, “That was pretty hot, I must admit.”

I was enjoying the show as Gail dropped to her knees, removed the clit clamp, and buried her face in her bush while grabbing her ass hard and pulling her tighter to her face. She ate her pussy and finger fucked her for five minutes until Suzanne shuddered and had a huge orgasm.

 “Oh fuck, that was incredible. When can I eat you?” she asked.

“Soon, my sex slave, soon. You still need some more foreplay,” Gail said.

Here she was naked, and me nude, with Gail fully dressed. What's wrong with this picture?

Gail said, “Cover your tits with one arm and your bush with your other hand.”

Gail then lifted the blindfold for me to see Suzanne as Gail began to stroke me. Suzanne looked so hot.

Gail said, “Spread your clit curtains and finger yourself,” which Suzanne did dutifully.

She then played with her nipples and proceeded to have a huge orgasm. “Ohhhhhh myyyyyyyy fuckingggg goddddd,” she screamed.

Needless to say, I had a huge hard-on that Gail was stroking in a great way.

“Don't come yet, big boy,” Gail said as she squeezed my balls hard to slow me down.

“Okay Suzanne, now strip me you fucking cockteaser,” Gail said as she took off my blindfold completely.

Suzanne got close to Gail kissed her and started to unbutton her blouse which then fell to the floor. Then she unzipped her skirt too. Gail was standing there in the skimpiest of undies. The kind with two tiny triangles that only covered her nipples and one that barely covered her pussy lips.

Suzanne said, “You are fucking hot, this is the type of body I dreamed about.”

She proceeded to feel her gigantic mounds and finger her cunt. Gail then got totally nude and they both went at it with a vengeance.

Gail looked at me and said, “Time to get ready big boy, and help us cum.” 

Suzanne got closer to me and said, “Oh my god, you're so big and this is what an uncut cock looks like. You are much larger than hubby,” as she stood there stroking me. “I've never been with an uncut cock.”

Gail replied, “Uncut guys last longer because the extra skin reduces the friction, trust me you will enjoy his staying ability, he can fuck for hours. Go ahead bend over and put him in your mouth. They all taste the same. Give him a good sucking.” 

Suzanne did as she was told. She then wrapped her lovely lips around my cock and gave me a great slurping. 

“OK, stop bitch, and stand up and get over here,” Gail ordered.

 They were rubbing their tits together and grinding their cunts so I stepped close and had Suzanne undo the handcuffs as she played with my ass. I put my hands on both their butts and pushed them together hard and stuck my manhood between their hips which touched both their cunts. My cock felt like a hot dog between two bushy buns. I then slipped my middle finger up each of their assholes and rammed my fingers in hard.

I heard a few “Oh my gods” and “Oh fucks” as they both moaned.

“Are you ready to do 69 girls?” They both nodded yes.

I led them to the bed. I said to Gail, “Her mouth has never eaten a pussy and her pussy has never seen a woman's mouth – be gentle.”

Gail winked at me and said, “I'll try, NOT,” and threw Suzanne down on the bed and dove between her legs and licked from her ass to her clit while manhandling her tits until she came.

“That was incredible,” Suzanne said. “Now let me do you.”

Suzanne mounted Gail and flicked out her tongue and licked her asshole and cunt until she came. Then, they did sixty-nine with Gail on top. I walked over to the side of the bed while stroking myself and I felt like I was going to cum.

I got close to Gail’s ass and shot five huge cum shots on her ass crack and Suzanne's face at the same time. Suzanne was shocked at first but then knew what happened and said, “I guess that's the thing guys do when two girls are going at it. Yummy.”

“Okay, time for tribbing,” I said.

Suzanne looked unsure about what to do but Gail pushed her down hard on the bed and spread her legs wide. She then spread her legs and mounted her clit to clit wishbone style.  They started to grind with a vengeance until they both had tremendous orgasms.

Then, they both sat on the edge of the bed snuggling and Suzanne said, “Stand in front of me big boy, and let me measure that uncut cock.”

Gail slowly removed a tape measure from her purse and they both began to measure me. They did it from base to tip, around the head, and back to my balls. Then, they measured my girth.

Suzanne said, “Hmmmmm, 6 inches long and 13 inches from top to bottom, impressive. That’s one nice cock.”

Gail said, “This is more important, he's seven inches around girth ways. That puts him bigger than 95 percent of guys. We are two very lucky girls.”

Then they put the blindfold and handcuffs back on. I gladly obliged as she took my cock in her hand and squeezed the last bit of cum out into her mouth.

“Yummy, cummy again,” she said as Gail fondled my balls.

I felt someone kneel in front of me and kissed the tip of my cock and then began a great blow job. Gayle took off the blindfold and Suzanne looked up and said, “Give me a huge load big boy,” which I obliged by giving her five huge spurts as she gagged until I went limp.

Gayle said, “Suzanne, you little slut, you haven't even kissed him yet, but just sucked his schlong and swallowed all his jism.”

She realized that was true and said, “I kissed his dick first, that should count." 

“No, you little slut, you must now be punished,” Gail said as she put the handcuffs and blindfold on Suzanne.

Gayle positioned Suzanne with her ass in the air and spread her legs and straddled Suzanne’s face and made her eat her pussy and ordered me to spank her hard. I gave her about twenty swats until her ass was beet red.

I then led Suzanne over to the huge sliding doors overlooking the patio off the bar. Our friendly bartender was outside getting a smoke and he looked up at the three of us nude with Suzanne blindfolded and handcuffed. His jaw dropped open and he gave a double thumbs up. I removed the blindfold so she could see and she blew a kiss to the bartender and dropped to her knees and started to suck me while Gail lay on the floor to eat her out. I came a ton all over her face and she then had an incredible orgasm.

I then got rock hard again and said, “How about some doggy style and anal?” Suzanne said, “I've never done anal before, does it hurt?”

Gail said, “A little, but it's an incredible pain and Jim has a perfect girth for it. You'll love the sensation and you'll be eating me out at the same time.”

“Ok,” she said shyly as I had her kneel on the bed and stick her ass into the air. Gayle positioned her cunt by her face and said, “Eat me now, my sex slave”. Suzanne went at it with a vengeance. I lubed up her ass with KY lube and inserted three of my fingers to stretch her cute butthole.

“Oh my god,” she screamed in a pleasurable way, “Give me your huge cock now.” I slowly removed my fingers and went over to Suzanne's mouth and said lube up my cock with your mouth and assume the sixty-nine position again. They got in position and I put my cock in Suzanne's mouth and I almost came. I went back to Suzanne's ass and spread her ass cheeks and put my tip at her hole.

I asked if she was ready and she said, “Yes, take my ass please.”

My balls were hanging in Gail's face.

Gail said, “After you enter her, I'm going to suck your balls and finger your ass.”

I pushed my tip in and she moaned. I then slowly pushed in inch by inch until I was balls deep and I thrust for about five minutes until I came gobs in her ass while Gail was doing her magic on my balls and ass. We then all collapsed in a sweaty heap.

Published 
Written by Jimclark
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