Cheesesteaks and Paradise Pt. 05

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Variety is spice. Another virgin gets a lesson.
2.7k words
4.18
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Part 4 of the 6 part series

Updated 04/03/2024
Created 03/17/2024
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"I'm going out for a while, Ray. Can I pick up anything for you?"

"No, babe.I have some chores. I'll go out later. Anything that you want for dinner?"

"We still have most of the appetizers from the Chinese restaurant. That will work. I hate sex on a full stomach. I hate all the farting."

"I hear you. I'll take care of everything. I have a client zoom in an hour and then I have to go to the hardware store."

She kissed me goodbye and went out. I sat down at the computer and checked my email. I had two new responses. Both from couples. Both looked interesting. One couple had a picture of the female on a sex swing. Didi had to see this.

My zoom meeting ran longer than I thought it would and actually, it wasn't all that necessary as I had my work done and put to bed, it was the others on the call who unnecessarily prolonged it. I checked my mail again and Steve had sent a nice letter written mostly for Didi. That was nice. I remembered that we had another virgin to deflower later on and that got my idle motor in gear.

Didi and I were devouring the rest of the Chinese food leftovers and yes, they were still mighty tasty. The doorbell rang and Didi welcomed our guest to our table. After some quick introductions, Sami nee Samantha fell quickly into our rhythm. At first, she was quite reticent to reveal herself to us but with Didi's relaxed way, she soon loosened up.

"So, Sami, if I recall correctly, you've never had a man. All of your encounters were with women. Right?"

"Well, sort of. I've never been with a man. My only encounter with a man was with a guy who exposed himself to me on the street. That was the first and only pe...pe...penis. Other than that, no." She was repressed, traumatized, confused, and tense. I considered her "presentation". I looked her over. With her ginger hair and freckles, I thought she made a fine fucked-up colleen.

"And women?"

"I had a few affairs with women who came on to me but I never pursued it."

"Tell me more. Did you like them?"

"One or two, the answer is yes, Others, not so much. I-I-I think I was looking for something more." She looked downward and a little sad. She was fairly tall, maybe five foot ten, and average sized. She had a firm physique without being muscular. It was obvious that she exercised. Her breasts were a good 34B and her hips were sturdy. She wore a pair of shorts which showed her long, beautiful legs. She wasn't bad looking by any stretch of the imagination however, her disposition and her make-up made her look pale and plain. It was obvious that she was tightly wound. It was evident that she needed a make-over.

"Do you use toys?"

Sami sighed, "Unfortunately, that's all I use these days. Although I am techically a virgin, I probably don't have a hymen anymore. Frankly, I'm tired of the toys. They are cold. I need something more..."

"...More? Say like human touch?"

"Exactly. That's a good starting point."

Didi thought for a few minutes and then got up, taking Sami's hand and said "Follow me." Didi led her into the master bath. I sat outside on the deck, drinking my Courvoisier XO and toking on a joint. I had a feeling they would be a while. I might have nodded out under the stars. It was some time later when Didi stroked my shoulder and woke me. "Come with me," she said. "Sami is ready. We had girl's time and I did a makeover. Then we enjoyed each other. But now she's ready for you so get up and come with me, please."

I was fully awake now. I told her to wait while I go to the bathroom. She refilled my 'yak and went into the bedroom. Sami was stretched out on the bed. This was a different girl. This girl was not the wan waif that walked into my house. Didi had done some work on her, Her lips were now ruby red and her pallor was replaced by rouge and mascara. Her ginger hair was brushed out and braided. Her body was still covered in freckles but now the contrast was subtly very sexy. Her pubes were shaved with a fringe, shaped and looking a lot like my dessert.

She opened her eyes as I gazed down upon her. "For a little Irish girl, those freckles are sexy. I'd like to play connect-the-dots."

"What little Irish girl?" she laughed. "My background is Czech and Polish! You know, it's a big gene pool!"

I laughed at my presumption and apologized. "Look, whatever your ancestry is, you look extremely fuckable."

"I want to fuck you, Ray. I've already been with Didi...she loosened me up...and she told me how good in bed you are. Please show me."

Didi started to strip me. When she unbuckled the belt and let me shorts drop. my commando dick flipped up and nearly hit me in the gut. "Voila!"

Sami got up at the edge of the bed. She turned over and propped herself on her elbows. I stepped closer and was my manhood was a foot from her face. "Let me see this thing," she said. She reached out and held my dick in front of her, examining it, feeling and caressing the balls, circling her fingers around the glans. Didi pointed out various parts. She studiously examined it until she took hesitently put it to her lips. Gently tasting the spongy meatus, she slowly took more in. Didi was next to her, whispering in her ear. She started to swirl her tongue around the head as my penis got stiffer and I began to drip pre-cum. She delicately licked it up. "I'm very wet. F-F-Feel me." I put my hand into her crotch, and yes, it was sopping.

I pulled my dick from her mouth. "Did you like that?"

"Yes. It was different...but nice."

"You can have more of that later, if you wish, but right now you're ready. I am going to enter you very slowly. If you want to stop at any time, just say so, okay?" She nodded. and rolled onto her back. I got up on the bed between her legs. Didi placed my stiffy at the entrance of Sami's vagina. With her other hand, she spread her lips apart. I gently entered her, just putting the head in. I felt no resistance and slid a couple of inches in. She gasped. I felt her sphincter squeeze and then relax. I held my position for a couple of minutes until she pushed her vagina, pulling me in deeper. When I had all seven plus inside her, I began to slide out, hold it and slide back in. Yes, she was very tight but her sugar walls adapted quickly. Didi sat on the side and watched, As she watched, she was jilling herself and saying encouraging things to us.

Sami began to pick up the tempo. I moved up pressed myself deeper, about as far as I could go. I leaned down and took a nipple into my mouth. She gasped again and pushed her clit against my pubes. I took the hint and ran my fingers around it. She started to shake. She whispered, "Fuck me. Fuck my virgin pussy. I'm so close. Fuck me." I found her whispering unique.

"Let it go, Sami, let it out." I pumped long hard strokes at her urgent pleadings. She began to shake, then arch her back and then writhe. She began to moan and grunt. She then cried out, "Yes! Yes!" as she came, Her pussy drenched my balls and I couldn't take the pleasure of her tight sleeve any longer. I sprayed her insides with cum, shooting about five salvos deep into her womb. I collapsed on her as she squeezed my body in a final orgasmic seizure. Still inside her, we held each other as regained our breath and composure. I heard Didi squeal in delight.

Sami lay flat. She knew that she was just fucked royally. "That was so good, Ray. I felt so full. I thought it would be like a dildo but it was alive and it felt warm inside. And then your cum...! Wow-wee. I'm a fan. Cock feels great!"

"Indeed, it does," said Didi as she crawled next to us, kissed Sami and then held us. After a few minutes, she said, "Now, I want you to clean him up while I clean you up." Sami did as she was told and swung around under me, tasting my now semi-flaccid cock with our combined syrup. This girl was enjoying herself.

"I think I love cock. Like, I was going with women because I wanted to cum, It wasn't like I had an aversion to cock, it's more like it had an aversion to me."

"Maybe you weren't giving off the right pheromones," I said. "Or maybe, you were afraid and giving off a bad vibe, like "Stay away" or "Don't touch me."

"I think it was more like the latter. I was afraid of men. I grew up in a family of men - mostly assholes - and I tended to steer away from men. But, I don't think that will happen now, I think I am over that for good. Can we do it again?"

"My dick can handle it? How would you like to do it?"

"Hmmm...I'd like to ride you with me on top and I'd like to go down on Didi at the same time. Have the best of both worlds, you know?"

"Yes, indeed, I do. I think we can figure that out." I rolled over on my back.

Didi suggested that they lick my cock together. That was a great idea especially since I wasn't hard yet. Two tongues, one hungrier than the other and the other an artist, got me hard in no time.

Sami got on top and placed her pussy above my cock. "Wait," Didi said as she leaned over and aimed my stiffy at Sami's hole. "Slowly, a little bit at a time...get comfortable with it." She slowly lowered three inches. She gasped as the glans passed over her g-spot. She backed off and did it again - and gasped again. Slowly, she sank down eventually taking all of it. As she sat on my cock, I felt her muscles contract and expand, squeezing and releasing my cock.

Didi lay back on my chest. I held up her thighs and pulled her higher. Thank God she's petite. When I had her positioned, I said to Sami, "The way that you are pulsing on my penis tells me that you've been working on your kegel exercises. Don't ever stop them."

She giggled and leaned over to kiss Didi's nether lips. I lifted my knees and began pushing in at a different angle. For a long time, could have been a half hour, we fucked in this configuration. Didi was the first to cum, arching her butt under Sami's mouth. "Right there. Right there. Oh, yes...yes...yessss!" She came in a minor deluge.

Sami's face was all wet and she was getting close. She was twiching and shivering and shaking. Didi scooted off me and as Sami raised up, she began to lick Sami's clit. That flipped Sami's switch and she began to cry out and pump on my shaft with vigor. I flexed my glutes. She slid up to that spot where she first gasped and slid against it. That did it for me as we both started to cum again. She squeezed and drained every cc I had in me. Her face turned red and her toes curled. She lost it. She sprayed my cock, my whole crotch, Didi's face and half the bed. She held the last spasm, and panting and gasping, she released it. We stayed in that position until my cock went soft and slipped out. She rolled off me as my creamy load leaked out of her vagina.

We were silent for a long time, except for the occasional kiss. Finally, Sami broke the silence. "I have to thank you both. That was really, really good. I never came like that, so intense, so focused. I couldn't have asked for more caring, more sensual or nicer tutors. I'm just sorry if I was so nervous."

"You're very welcome," said Didi. "It was our pleasure. Hopefully, now you'll go out and not scare the boys off. Don't be afraid to show some cleavage and watch their pants tent up. You'll know that whatever is inside those pants might be your friend and not a source of fear or a power trip. Let us know how your dating goes and if you ever need a refresher course, you're more than welcome here."

"You get a whole lot more from us than college credits." They laughed at my lame joke.

Eventually, we showered like three little kids. Things got a little serious when I rubbed my cock between her ass cheeks and around her pucker. "Save that for the next time, Stud," said Didi as she rinsed off.

As we dressed, Sami said, "You know, my pussy is sore. Now I understand why they say it's like getting off a horse! That last fuck was bronc busting, I swear!"

"So, tonight, when you are fingering yourself and reliving this event, use some cool beauty cream to rub on it. It often works for me. Also, be gentle with yourself."

"Good words to live by," I said.

Didi and I had a late-night glass of wine and went to bed. She said, "That was fun. Wasn't it?"

"Yes, it worked out well. Lucky us, two nights in a row."

"We turned two kids. We flushed their pipes out. I'd say it was a major score, wouldn't you?"

"I would. Not that I would make a habit of it, but it was a good thing to do. I'd say we helped the community. Now, I want to take a bit of a rest. Maybe, we'll do it again with her in a few weeks."

"Okay. I'd like to meet up with a seasoned couple next. Maybe they could teach us a few things."

"Like what?"

"Oh, I don't know. I'm open to anything except poop and pain."

"That leaves a lot."

"Yes, I guess it does. There are still fantasies I want to fulfill. But, not at this moment, my little pussy has to recover and my tits - my tits are all black and blue."

"I wasn't coming on to you but I know how you feel. I have the same problem with my dick. It's sore. It stings. It's in the recovery room, so to speak."

"You know, I have just the thing." She ran into the bathroom and came out with bottle of aloe lotion. She poured a generous amount into her palm and then lightly caressed and coated my cock. At first, I jumped at the immediate cooling effect. It only lasted a moment until it felt better. She refilled her hand and rubbed it all around her mons. "Oooooo..." Again, I knew how she felt.

We lay on the bed and kissed until we fell asleep, Didi spooned in my arms.

During the next few weeks, we were both very busy and did not see each other. I was out of town for five days and then she was out of town for a few days. Also, I was involved in a gallery showing and that took me away. Finally, when schedules had settled down, I called her.

"Hiya, Didi. How have the last few weeks been? Successful, I hope."

"Yes, it was and back at cha." She giggled. "You know, I was just thinking about you and your beautiful penis. Guess, where my fingers are?"

"Now there's an image I can enjoy. If I know your cooch, it's probably dripping. I've missed both it and you."

"I like how you prioritize. So, what's doin'?"

We chatted a bit and then decided that he had to meet up later to reacquaint our organs. When we did meet up at our favorite cheesesteak joint, it was as though we were of one mind. And that was, eat light by splitting one, eat fast and fuck all night. I liked this relationship.

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oldhippie1949oldhippie194925 days agoAuthor

Who fucking cares?

AnonymousAnonymous25 days ago

You've been writing for 16 years and have less than 700 followers. Not very inspiring.

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