This is a romantic story of how I helped an ex-lover fulfill her desire to have anal sex.
I am a businessman who in the 12 years since graduating from college has started and built and very successful business. Part of my success comes from my willingness to travel over 50% of the time. This schedule allows me to stay in touch with friends and old acquaintances. This story is about one of those trips and how I helped an old college lover lose her virginity a second time.
The trip was taking me to Memphis a city that I had never visited. As I normally do I check to see if there is anyone in the city with whom I might want to get in touch. It turned out my college lover Jill lived there. When I discovered this it brought back a flood of memories and a question about why I hadn’t stuck with her. She was smart, sexy and willing to try just about anything in bed. My drive for business success was the down fall to the relationship. Well I thought, she’s a perfect candidate for at least a dinner.
I called Jill and after the shock wore off she agreed to dinner. As is usual I travel first class and only dine in the finest restaurants, so when I told where to meet she was impressed.
I arrived prior to the appointed time and was seated at a table. I wondered if Jill might look much different 12 years after we last saw each other. My seat had me facing the entrance so I was watching each patron as they arrived. Than Jill entered. Wow, she wore a black slip dress that ended a couple of inches above her knees and spike high heels, Watching her walk to the table with that air of confidence that older women have, made her look better than I remember. I stood and gave her a kiss taking in the smell of her exotic perfume. Time had only improved Jill. Her 5’5″ frame was in great shape evidenced by the slinky fit of the dress. She didn’t seem to have a bra on yet her 34C breasts stood firm.
I exclaimed to Jill how she looked better than I remembered her. She thanked me and kindly expressed the same sentiment of me. We got into our dinner and the catch-up on our lives. She had two children from a marriage which ended in divorce and was now working as an office manager. The dinner went on with good food and wine putting us both at ease. Eventually our discussion turned to our “good old” college days and the good times we had. We started to reminisce about our sexual adventures. At one point Jill said the only thing we hadn’t done in college was have anal sex.
“Why was that?” I asked
“I didn’t think it was right then.” Jill replied
“So have you had anal sex yet?”
“Nope, still haven’t done it”
“Still don’t want to do it?”
“Oh I want to do it, but my ex-husband didn’t think it was right and I haven’t had the opportunity since we split.”
“You don’t know what you’re missing.” I exclaimed.
“You’ve done it than?” Jill asked.
“Multiple times and twice helped friends give up their virginity.”
“How did you do that?”
“Have anal sex?” I jokingly asked.
“No help them give up their virginity.”
“Oh, I went out of my way to make it special and to insure that she was very relaxed.”
“Describe what you did.”
“No I never do that, I only demonstrate.” Smiling and looking into her eyes.
Jill paused for a moment and than said ‘Would you demonstrate for me?”
“On you?”
“Yes, I want to experience anal sex and you were a great lover.”
“I am only in town tonight.”
“I’m free tonight,” Jill smiled.
“Well that settles it. Would you like to come to my room?”
“When do we leave?” said Jill as she ran her hand up my thigh.
Raising my hand, I waved toward the waiter, “Check please”.
We stood and I placed my hand around Jill’s waist pulling her close to me, taking in her intoxicating aroma.
In the cab to my hotel I told Jill she must follow my instructions otherwise it wouldn’t work.
Jill smiled, “OK,” and she gave me a deep kiss.
Opening the door to my hotel room I told Jill to stand in front of the floor to ceiling mirror which covered one wall.
“Step out of your shoes.”
She did as instructed.
Than I came up behind her and wrapped my hands around her waist, leaned my head down to her neck softly beginning to kiss her.
“Its nice to have you back in my arms,” I whispered.
I slid my hands up over her breasts and Jill moaned. Than continued moving my hands to the shoulders and pushed the spaghetti straps over her shoulders. Slowly moving my hands down I pushed the dress off her breast revealing her large brown nipples. We were both watching this in the mirror. Fondling a tit I reached behind her and unzipped the dress, watching it go loose. She smiled into the mirror as I pushed the dress down until it fell to the floor in a pool of fabric.
Looking at Jill in the mirror it was just as if we were still in college.
“Mmmmm,” I moaned. Kissing her neck.
Jill pressed back against me in pleasure and smiled into the mirror. Looking over her shoulder I started to slide my hands down to her thong panties. Reaching the waist band I pushed them off the hips down her legs until gravity took over dropping them to the floor. Now that’s a change I thought looking at her shaved pussy.
Stroking her slit I murmured “no hair, that’ new.”
“For my bikini and it feels good,” as she moved her hand down and pressed mine deeper into her slit. We both watched intently as I slid a finger into her cunt. Jill moaned.
Kissing her neck as I slid my finger out, I said “come with me”. Taking her hand I led her to the bathroom and said “stay warm,” while placing a soft hotel bathrobe around her.
Turning and kissing her, I said, “I want you to relax”. Than I went to the bathtub and turned the water on.
‘Relax, I’ll be right back,” as I left the bathroom.
I returned to bathroom naked, after undressing.
Jill smiled “now you look much more comfortable” as she reached out and stroked my erect cock.
“Get into the bath tub Jill before I lose control!”
“Okay,” as she stepped into the tub. “Mmmmm comfy warm,” she said.
“Relax” as I took a natural sponge and began to stroke her shoulders.
“Mmmmm,” moaned Jill as she leaned back closing her eyes.
I worked my way down her body with the sponge paying particular attention to her breast and clit. This elicited further moaning and purring from Jill.
My finger also stroked lower between her legs until I felt her anus. I circled her anus and brought another moan out of Jill. Than I pushed the tip of my finger into Jill. She moved her hips around clearly savoring the feeling. Leaning over and kissing Jill, I pushed my finger deeper. “Soon you will have the real thing,” I whispered, “but now its time to dry off”. Jill let out a sigh as I slid my finger out of her ass.
Lifting her out of the tub I once again wrapped her in the robe. Than guided her out to the bedroom. Standing behind her I slid the robe off and instructed her to lie on the bed. Jill was on her back with her legs slightly spread. I was ready to jump on her right than, but instead I pulled a sheet up over her breast.
“Just relax Jill. Close your eyes.”
When she did I climbed onto the bed and started to kiss her head with short soft kisses. I was going to kiss every square inch of her body in my efforts to relax Jill. I gently sucked on her ear lobes, down over her eyes and softly probed her mouth with my tongue. Moving down her chin I covered her neck in kisses. Going from there, I covered each arm in kisses and finished by sensually sucking on each finger. Returning to her neck the direction took me towards her breasts. I climbed the slope of one breast until I reached the peak and took her nipple into my mouth. A strong moan accompanied an upward thrust of her body. Clearly Jill was enjoying this. Covering her stomach with kisses Jill began to squirm in anticipation, but I bypassed her pubic area and worked myself down the outside of one leg and up the inside. Jill spread her legs as I approached the junction between her legs. As I got close enough to smell her juices I jumped to the outside of the other leg working my way down to her toes. I spent time sucking each toe individually. Jill was moving around. I worked my way up the inside of her leg and this time went right to Jill’s pussy slit and kissed the length of it to her clit. It was like an electric shock hit Jill by the way she arched her pelvis. I backed away as Jill moaned in frustration.
“Turn over,” I quietly whispered in her ear.
She rolled languidly over and once again spread her legs apart. Moving to her head I began to kiss down her neck and over her shoulders. I covered each arm with moist kisses and gently sucked each finger into my mouth. There was an occasional moan from Jill. I worked my way down her back and focused on the small of her back going as low as the beginning of her crack.
I skipped over her ass and went up and down each leg. As I got to the top of her legs I could see her cunt dripping juices. Kissing up one cheek of her ass I reached the top of her crack. Gently spreading her cheeks apart I softly kissed my way down to her anus. Sticking my tongue out I circled her anus. Jill let out a huge moan and I thought she was going to cum than.
Kneeling between her legs and positioning myself I slid my cock under Jill until it touched her clit, eliciting another loud moan and thrust of her hips. Then slowly kneeling up my cock dragged over her slit up over her anus. Jill was moaning continuously now. I slid my cock up and down several times until there was a sheen of moisture over Jill’s anus.
Leaning over I whispered in her ear, “kneel up”. She did so quickly. I kissed her back several times and than knelt up. Then taking my cock in hand I gently pressed it against Jill’s ass hole.
As might be expected of a virgin she instinctively tightened up. Leaning over her back again I gently caressed her breasts while kissing her and telling her to relax. I felt her anus relax and began to press inwards. Jill moaned as she felt her ass being spread open. Slowly the head of my cock went passed her spincter and I paused. I asked Jill, “are you all right?”
She responded in a moan, “I’m wonderful!”
Pressing deeper I began to feel Jill pushing back. Finally, I was all the way in Jill’s ass with my ball’s resting on her clit. Pausing I let my cock throb for a moment in Jill’s ass. Than I drew about half way out and pushed back in. Jill moaned. I started to pump in and out. I pulled all the way out and briefly admired the gapping anus before shoving myself all the way in. Jill screamed in pleasure. I grabbed her hips and started to pound her ass while leaning over and instructing her to stroke her clit. She did and this caused her to begin pushing back on my cock.
I was beginning to moan and my cock was throbbing in Jill’s ass. Tightening my grip on her hips I screamed as my cock exploded in a hot stream deep into her ass. The moment Jill felt this hot pressure she came in a massive orgasm. Pushing her ass hard against my cock she sucked rivers of cum out of me. It went on for what seemed like forever until we collapsed on each other.
My cock slowly softened and finally slid out of her causing Jill to moan again. Reaching down I stroked her ass covering my finger in my cum.
“Here,” I said “a taste of your lost virginity.”
Jill opened her mouth, sucking my fingers in and licked them clean.
“Mmmmmmmm,” was her response.
“Well, was it worth the wait?” I asked.
Smiling Jill said “Absolutely… shall we do it again?”