Sexual Soul Mate Pt. 02

Story Info
Fulfilling anal sex, number one on the bucket list.
2.5k words
4.44
25.6k
9

Part 2 of the 4 part series

Updated 06/10/2023
Created 10/19/2014
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Loving50
Loving50
186 Followers

Without knowing what to expect, Melanie was a bit apprehensive wondering just what a 'no strings attached' relationship would look like. She left his house after that first private encounter with a lot of questions and no answers. Would she hear from him again? When would they get together? Would he have regrets about inviting her to his home? Would she have regrets?

Although she was distracted by the questions, she was also tingling with excitement as she fought the traffic in the late afternoon. Thinking back on their love making was already creating memories for her that she knew she would use in private, masturbating moments. Although she hoped that it wouldn't be their only time together, she was satisfied that it was memorable enough to last her for a while.

By the time Melanie reached her house and checked her email, there were already a couple of messages from him. He wrote about their love making, the sensations he felt, how she was perfect and tasted even better than he imagined. In other words, he said all the right things. She fired back a message of her own telling him how she felt and how her body just tingled just by reading his messages. Clearly, they were head over heels in lust with each other.

Over the following week Melanie and Jack exchanged emails daily. Sometimes they sent e-cards or images of couples in erotic positions with an 'I want to fuck you like this' message. Melanie even googled 'fwb rules' hoping to find some guidelines and instructions as to how the relationship should work. No guidelines to be found, by the way. Instead, she became bolder in her emails and asked him for information. Without sharing many details with her about his past experience, he reassured her that this would work as long as it did for them both. Cryptic and certainly not the detailed rules the Melanie would have preferred, but it would have to do.

Two weeks after first meeting, Jack once again invited Melanie to his house. Excited and still a little nervous, she drove over and once the door was closed behind her, she threw herself into his arms. They clung to each other like a dying man would cling to a life vest. Without a doubt they were lovers and every time they came together that bond was solidified.

Again, they went to the lower level and soon were buck naked next to the bed. Although it was freezing in the house, he didn't allow her to cover up with sheets or blankets and he kept the lights bright. He wanted to see her, he wanted to see everything. Slowly he turned on the charm, igniting all of her erogenous zones. Situated between her legs, she gasped as he dipped his head down but then used his palm to stimulate her. Soon she was begging him to lick her, his smile never wavering as he teased and tempted her for a very long time.

Her begging became desperate pleading until he dipped his mouth down to move over her clit. Moisture dripped from her pussy as he slowly lapped up every drop. Her soft moans became loud cries and she reached for his hair, pulling him in closer to her. The feel of his beard tickling her inner thighs and her tender pussy flesh drove her crazy. She reached down between her legs and fingered the soft hair as just inches away his tongue worked it's magic. Her back arched and her hips bucked as he relentlessly attacked her tender flesh. Never before had she experienced anything like him. She came twice if not three times as he ate her out. It was as if he knew exactly what to do and when. He was her perfect sexual soul mate.

That day Melanie was just a day past her period so they agreed that they wouldn't use a condom. They moved from one position to another, finally ending up with her riding him while her breasts bounced in his face. Still he stayed hard as he so easily could, until she finally moved off of him and spooned into his front as they lay on their sides. She reached between her legs and grasped his cock, placing it at her hole. Positioning was, of course, important and she moved until the head of his throbbing cock was lined up perfectly. Guiding the head into her hole, Melanie ended up moving her upper body further away from him. That gave her the leverage to thrust back harder against him, feeling him deep inside of her and then feeling him pull almost all the way out. His arms encircled her and the sweat from his brow dripped onto her back. They fucked like that for a long time until he groaned loudly and released his hot cum deep inside of her. Slowly they came back together as his cock slipped out of her cunt and he held her tight.

Each encounter, each moment of climax was magical between them. She regularly licked and sucked his cock, trying to coax the cum from him. Although she was never successful at getting him to cum in her mouth, it wasn't for a lack of trying. She was determined to taste his cum someday and was willing to work for the pleasure.

One day after a couple of months of regular meets, Melanie was getting dressed when she sat down on a chair to pull on her socks. Jack sat in front of her with shorts and a t-shirt on. Melanie stifled a giggle when she noticed that Jack's fly was down on his shorts. She could see his briefs and was so tempted to reach over and grab him but time kept her from slipping her hand in his shorts, unfortunately. Jack was reflective at that moment and suddenly asked, "So, what things are on your sexual bucket list?"

The question startled her but after a moment she said, "I can think of two things. First, I've always been curious about having a threesome and I have always wanted to successfully have anal sex."

Melanie blushed, surprised at her honesty. Jack was obviously pleased however, and had more questions for her.

"Would you want a threesome with another man or a woman?" he asked with a mischievous grin.

At that Melanie responded with a quick poke at his open fly with her foot. They both laughed as she answered carefully, "I think I would be open to either. I would love to try it with another man but I'm open to a woman also. You know that I have interest in women but have never acted on it. The problem would be to find a safe and willing person that was attractive to both of us. I think that's really hard to find."

Jack nodded and said, "Fair enough. So, tell me more about wanting anal sex."

Melanie was feeling very self conscious at that point and deferred to him. "You tell me. Do you have any interest? Have you ever?"

Shaking his head, Jack answered, "No, I've never experienced it successfully. I've had a couple of lovers who were willing to try but always ended it before we could get my cock in. Of course, I would love to do it, especially with you."

With that he leaned over and wrapped Melanie tightly in his arms. Holding her close to him he guided her back into the bedroom and began stripping her bare once again. Schedule be damned!

Over the next couple of weeks the two lovers wrote back and forth about anal sex and how much fun they would have experiencing it together. He shared with her that he had been researching the act in order to make it as painless as possible. She was touched by his efforts and although she already felt so safe with him, she knew she could trust him with that intimate act.

One day, just before the holidays, they met at a sex shop in a trendy area of town. She had been there before and wanted him to experience it. Melanie got to the store first and looked around while she waited. She noticed a book titled, 'Anal Sex' on a shelf and sat down on the couch to look though it while she waited for Jack. The illustrations were fascinating and kept Melanie from noticing a man coming through the door. By the time she looked up, the leering man was sitting close to her on the couch. She was startled but tried not to over react, just scooting back a bit. He grabbed the book from her hand and began thumbing through it. Melanie started to get up just as Jack walked through the door. Assessing the situation quickly, Jack moved over to the couch and gave the horny man a long, intense stare. It didn't take long before the man got up and moved away from them. Then Jack and Melanie kissed and cuddled on the couch, looking at the anal book. After looking around the store together and laughing at some of the merchandise, they left to the relative privacy of his van.

Over Christmas vacation when they both had extra people at home, Melanie and Jack made a plan to get together. Going to his house was not possible but the weather was cooperating with pretty warm winter temperatures so they made a plan to get together in the van. On that particular day, Melanie dressed carefully while thinking through the limitations of being in the van. They met at a park that was usually deserted in the winter. Sure enough they found the privacy they needed.

Jack was privately put out at first that Melanie had worn nylons and a skirt. At the first kiss she knew that the wheels in his head were turning quickly, wondering how they would manage. When they parked, Melanie moved into the back. Sweet Jack had removed the middle seats and laid down the back bench so it was like a bed and he had brought pillows and blankets to make things comfortable.

Melanie slipped off her heels as she sat on the bench and watched him approach her. Kneeling between her legs, his hands began to wander over the silky nylons and soon he realized that she was wearing thigh highs. His smile broadened as he whispered, "You little vixon. You think of everything."

They kissed passionately as their hands began to wander. Her skirt was soon pushed up around her hips and his hands couldn't seem to get enough of running over the silky smoothness of her legs. By silent agreement they didn't undress completely but only removed those items that absolutely had to go. Her panties, his jeans and brief disappeared to the floor of the van. Everything else could just be loosened or pushed aside. As soon as his cock was out and throbbing, Melanie began to caress it with her nylon covered feet. From the look on his face, she knew that he had never been given a silky foot job. She loved that surprised expression on his face when she pampered him and the feel of his hard cock between her feet made her start wiggling on the seat.

Although they had to keep a watchful eye out for the police or even just other parkers, that was all just another part of the thrill. Neither of them wanted to get caught but being in a semi-public situation was a turn on, nonetheless.

After a time of amazing foreplay, Melanie knelt at the bench and offered Jack her wet pussy. She urged him on with small moans and grunts as he moved up behind her and slipped his cock deep inside. She pushed back against him as he thrust into her for quite a while. His ability to stay hard was incredible so she didn't worry about him cumming before they could try anal sex. Then finally the moment seemed right.

Melanie looked over her shoulder at Jack and whispered, "I'm ready, baby. Please put it in my ass."

Jack leaned in and kissed her deeply and then reached for the lube and a fresh condom. After applying the lube to his cock and her puckered hole, he positioned her sexy ass against the edge of the bench seat and placed his cock at the tight spot. They had prepared for it but Melanie still had to remind herself to relax and just let him do what needed to be done. They were both determined to be successful but he had let her know that he would stop if she asked him. She knew he could be trusted and that clearly helped her relax.

The head of his cock slowly pushed into her tight hole. As the pain grew, she willed herself to accept it, not unlike the pain of childbirth. She opened her mouth wide, willing her asshole to open and accept him as well. The pain grew intense even with all the careful planning and Melanie could clearly feel the head stretching her.

Suddenly, the pain reached a point where Melanie didn't think she could do it anymore and so she looked back, ready to stop him. Then, just as suddenly, the large head of his cock popped in and much of the pain disappeared. The pop was almost that, almost an audible one, and it took her breath away. He felt her slump against the bench and knew that the pain was mostly over for her. She turned, making eye contact, and said, "It's in, please fuck it."

With a loud groan he began to move deeper inside of her. Watching his cock move in and out of the tight hole made him start to shake. He knew he wouldn't last much longer but he wanted to reward both of them for their efforts. Slowly working his cock deeper into her ass, he reached around and fondled her beautiful tits. He loved the way they swayed and responded when he played with them and he knew she loved it too. After a time he grunted loudly and came hard in her ass, pulling her against him as he did.

Later, they lay together on the folded down bench and cuddled. They quietly talked about the experience and he kissed her passionately, thanking her for enduring the pain so they could both enjoy the pleasure.

After they dressed but before they parted that day, he said sheepishly, "Melanie, can we do that again? Not today, but again?"

She loved it when he looked so boyish and would ask her instead of just assuming. Kissing him hard, she said, "I would love to do it again. That was the most amazing thing ever."

Through emails they talked about the experience for a long time after that day. It was special to them because it was only theirs. The act brought their intimacy to a new level and after that day in the van, they always enjoyed anal sex together during their passionate afternoons. Special, intimate, rare and even a bit taboo, that's how Melanie looked at anal sex with Jack. She was glad she had endured the pain to enjoy the unique pleasure.

Comments welcome.

Loving50
Loving50
186 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
AnonymousAnonymous11 months ago

I have never had anal sex, that I was sure I had entered her. I think once I pulled out too far and when I tried to reenter, I may have been in the wrong position. She screamed NO and I stopped immediately. I apologized profusely and worried I had hurt her. Our anal sex became more oral then she fingered me. After a few times she used two fingers, and I was shocked but relaxed after a few strokes. Then she inserted a third and I lost all desire for the act. I think she liked doing that to me. We ended our relationship very soon.

Harsh61Harsh61about 7 years ago
Intimacy.

It seems like Melanie and Jack are exploring new waves into their affair gradually with a grace. The storyline as well narration is good to read..

AnonymousAnonymousover 7 years ago

I was 59 when my boss popped my anal cherry. We'd had a lot of foreplay where he fingered me and lubed me up well but when he tried to put his cock in it was like a burning sensation and I asked him to stop. We tried again and the pain did ease once his cock head was in. I rubbed my clit whilst he slid in and out of my tight hole and i had a powerful orgasm. Moments later he erupted deep inside me. When he pulled out I was shocked to see how stretched and open I was but within an hour my anus had closed tight again. I think if I'm honest I prefer a cock in my bum more than my pussy.

blue80driverblue80driverover 9 years ago
Descriptive

So descriptive like I was there. Very well written.

Enjoyslife42Enjoyslife42over 9 years ago
Well Written

Very nicely written, as you can feel the natural desire between these two people. Hope you write more.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

A Wonderful Weekend Her son's best friend saw to that.in Mature
Hot For a Retired Teacher Ch. 01 I meet Donna at a historic site, leading to fun times.in Mature
Moms at the Beach Ch. 01 Newly single Moms make tempting targets for enamored sons.in Mature
The Weekend Two days that re-awakened a young widow's sexuality.in Mature
HOT SHOTS: M.I.L.F Spring Break Loses his virginity to his girlfriend's mom.in Mature
More Stories