Join the best erotica focused adult social network now
Login

I Lose My Virginity, Again!

"Two times in two days."

19
17 Comments 17
15.8k Views 15.8k
3.3k words 3.3k words

I woke up in the morning to an empty bed. Jonathan must have left in the middle of the night. I was sorry that he had left, as my morning wood would have enjoyed another session with him. We had celebrated the loss of my virginity by indulging ourselves in an orgy of sexual acts through the early hours of the evening and into the night. I remembered how absolutely mind blowing it was when I fucked his hot, tight asshole. That is the point when we both fell asleep in each other’s embrace.

 

 

My plan for today was to find a job for the summer. I could not go through the summer sponging off Kathy; she was my stepmother.

 

My dad had remarried two years ago and unfortunately passed away in a car accident six months after. My mother, who left him to marry another man, had ruined him financially. Then he met Kathy, who was 20 years younger than he was.

 

She had washed the bitterness out of his soul and made him a happy man. Then disaster had struck.The car crash, in which he had passed away, left Kathy and me penniless with the exception of the house. Kathy had to find a job to support herself, and me, through the last months of my high school education. She never uttered a word of complaint and was the epitome of kindness towards me.

 

Kathy worked tirelessly to make ends meet, and I did not want to impose any further hardship on her.

 

After showering, shaving and making myself presentable for job interviews I hit the road to visit some of the outfits where I had done part-time work over previous summers. I had no success with any of them until I ran into one of my father’s old friends, walking out of a restaurant, which had just turned me down for a job as a waiter.

 

“Hey Jack how’s it going?” he greeted me.

 

After some small talk about college, and how Kathy was, he asked me if I was planning to work this summer. I told him that I was on the hunt as we spoke.

 

He asked if I had given any thought about working at the local country club. I admitted that I had not thought about that.

 

He told me that they were starting a summer camp, golf program for golfers six to fourteen. He remembered that I was a very good golfer having seen me often playing with my father in various tournaments. Then he startled me by asking would I want to head that program. He explained that he was the chairman of the board of the club, and if I wanted the job it was mine.

 

I asked him what it would pay, as that was my greatest concern. The figure he quoted was astronomical compared as to what I could earn as a waiter. It would permit me to live the full year while only doing some small part-time work when I returned to college and even to help Kathy out financially.

 

He told me to meet him the following morning at the club to finalize the details and to pick up the curriculum for the summer so I could look at it and make any modifications I would want. In addition, to decide how I would hire additional staff.

 

Elation and relief at this stroke of good luck washed over me. I even started thinking that I might hire Jonathan as my assistant.

 

I made my way back to the house had a bite to eat and retired to my bedroom. Last night had done a job on me. I immediately fell asleep.

 

When I woke up it was already dusk outside. I got up to go to the bathroom when I came out; I heard the sound of moaning downstairs.

 

Who can that be? Kathy is not due back until tomorrow.

 

Barefoot and in my boxers, I silently stole to the head of the stairs and looked down into the living room. I saw that Jonathan was in the living room. He was massaging the back of a woman who was lying face down on the couch.

 

That is Kathy! What is he doing with her?

 

Jonathan must have spotted some movement. He turned his face towards me and brought his finger to his lips signaling me to not say anything or make any noise. He then motioned me to come down.

 

Flabbergasted I crept down. Kathy had not moved. She lay face down with her head cradled in her arm and facing the back of the couch.

 

She is so gorgeous. What a beautiful body. No wonder Dad married her.

 

I approached Jonathan on tiptoe. He just kept massaging her body, which I had never paid attention to before. While Dad was alive, I perceived her as off limits, subconsciously, I guess. After Dad died I was probably too dulled by the event, and its consequences, to be able to perceive much of anything .

 

All of her five feet one inch stretched out along the couch, lying on her stomach, her long black hair raised above her shoulders, with her long for her size legs slightly parted. She had the cutest bubble butt ass, perfectly proportional for her small body.

 

My cock was poking out of the fly of my boxers. Jonathan took my hand and placed it on her ass. Then he cupped the fingers on my other hand and placed it between her legs. During the whole time he made sure that at no point Kathy would feel more than two hands on her body.

 

Reaching between her legs, I felt the warm dampness and heat of her pussy. I gently rubbed my palm against it touching a woman there for the first time in my life.

 

Kathy began making small mewing sounds of satisfaction. Lying there just savoring her moment.

 

Jonathan then brought his hands back into play massaging her shoulders. I guess that Kathy was so wrapped up in the moment that it took her at least thirty seconds before she realized that there were four hands on her body.

 

All of a sudden, she turned over startled. Her eyes grew wide and she let out a piercing scream.

 

Sitting up she covered herself with her hands, she kept saying, “Oh my God, Oh my God.”

 

She started crying and hiding her face in her hands.

 

I sat down next to her and wrapped an arm around her shoulders. Removing her hands from her face, I tried to wipe the tears. She just kept on crying and breathing with difficulty. I just held her and rubbed her shoulders until she calmed down.

 

“Jack,” she said, “You scared me. When I looked up, I thought you were your father come back to life. You look so much as he did. You even smell the same. Damn I miss him so much.”

 

“I know Kathy so do I, and I hope I have not offended you by touching you.”

 

“Oh, Jack I am way past that. What you saw you should have never seen. I have been so lonely that Jonathan and I have been fooling around together. I no longer have time to see anybody with work and all that… “

 

“Quiet Kathy, I understand and am not judging you. You are so beautiful that I could not help what I did.

 

She turned her face towards me and I could see her beautiful purple eyes. She gave me a shy smile and said, “Thank you, Jack.”

 

I just could not resist; I brought my face to hers, and I gently kissed her lips. She returned the kiss, and then I felt her tongue against my lips. She parted my lips with it and the gentle kiss turned passionate, our tongues probing and licking. Her breath was fresh and clean. I felt my erection, which had subsided during her crying, regain life, and soon I was rigid as a steel bar. Her arms went around my neck and her tits were against my chest.

 

Johnathan who had been a spectator during all this spoke up, “Jack did I not tell you that you would lose your virginity with a woman soon.”

 

Kathy looked at me and said, “Jack are you a virgin?”

 

I blushed not knowing what to say.

 

“Not completely,” said Jonathan.

 

“What do you mean?” said Kathy.

 

“Well, Jack and I spent the night together. He is no longer a virgin as far as males are concerned.”

 

I felt the heat rising to my face, as I blushed. She then started laughing much to my consternation.

 

“Why are you laughing at me?”

 

“Oh Jack, poor Jack I am not laughing at you. I am happy for you. I know you are not gay, I saw how your cock reacted to me. I will tell you a secret that your father and I kept from you. Your Dad was bisexual, as am I. We had a great sex life together sharing partners quite frequently. It was a wonderful time and never had I felt as free as while we were married. Your mother left him because she was too uptight to give him that freedom.”

 

“Really?”

 

“Yes really.”

 

“There is something else I have to tell you. I have lusted after you since we first met. Your father was aware and kept asking me when I would have enough courage to seduce you. I think he would have enjoyed it if you and I were involved. He was anxious for you to get a girlfriend so that we could both seduce her, and I could get my way with you.”

 

She then knelt between my legs after having taken off my boxers. My cock was rampant; she looked at it and tenderly took it in her hand.

emilywalker1
Online Now!
Lush Cams
emilywalker1

 

“May I?”

 

You can do anything you want with me.

 

“Oh yes, my sweet Kathy anything you want.”

 

Her tongue licked a swath from my balls to the tip. She opened her mouth and sucked on the head, before sucking the whole of my cock down her lovely throat. It was so different from my experience with Jonathan. Much more sensual and loving. I could feel myself dripping pre-cum and feel her throat muscles swallowing.

 

Suddenly she stood up, “Jack you did say anything. Right? I want to feel your cock in me. I want you to fuck me.”

 

I stood up and took her in my arms. I lowered my hands and put them on her ass. I then lifted her up; she was so light it was like lifting a doll. She put her arms around my neck and opened her legs. She was so wet and ready that I felt my cock slip into her tiny tight cunt. She then wrapped her legs around me and started thrusting up and down on my cock, while I bounced her up and down like a little fuck doll.

 

During all of this, we had completely forgotten that Jonathan was still there. She looked at him smiled and said, “Okay you dirty young man. I know what you want to do, go ahead.”

 

Jonathan came behind her and asked me to spread her ass cheeks. As I did he approached her placed his cock at her anal pucker and slid it up her ass. Kathy squealed with delight.

 

She was now so much tighter with two cocks in her. I could feel Jonathan’s cock rubbing against mine through her interior walls. She was so hot and so wet that I did not know how long I could hold back. I wanted this to be good for her. Fortunately, she was primed, and after a few strong thrusts, I felt her body quiver. Her arms and legs squeezed me even harder and I felt my cock go all the way to her cervix as she massaged it with the walls of her cunt. Her orgasm was climatic as she moaned, yelled and screamed that she was cumming.

 

I felt the pulse of Jonathan’s cock through the walls of her cunt, and then we both came at the same time flooding Kathy with our jets of hot cum.

 

I lifted her up and set her down on the floor, her legs wobbly.

 

“Oh thank you, Jack, that was so good, I needed that,” she said giving me a passionate kiss.

 

“Jonathan come here so I can thank you also. I know you set us both up and will always be grateful for that.” She then gave him an equally passionate kiss.

 

Jonathan said, “Look you two I will be going. I think you need some time to yourselves.”

 

“You don’t have to leave,” we both said simultaneously.

 

He smiled and said, “I have a hot date tonight.”

 

He turned and walked to the door as he started to open it he stopped.

 

“Kathy, are you truly bi?”

 

“Yes, why?”

 

“What would you think if I bought my date back here later? It might be fun.”

 

Kathy looked at him. “Am I right in thinking you want us to have a foursome?”

 

He smiled and nodded.

 

“Would she be up for that?”

 

“She will do anything I tell her, she is my slave girl. Besides that she likes women.”

 

Kathy turns to me. “What do you think Jack.”

 

“Kathy it is whatever you want.”

 

“Okay Jonathan, come by at ten; it will have given Jack and myself a chance to talk.”

 

After he left, Kathy came to me, wrapped her arms around me and kissed me until we were both out of breath.

 

“Jack, do you think I am a bad person? Do you think that because we made love we did something wrong?”

 

“Kathy, I don’t know what to think. I always really cared about you. Today I just realized that I am in love with you.”

 

“Don’t you care that I am older than you are and that I was married to your father?”

 

“You are only two or three years older than I am why should that matter. Besides, I believe Dad would have been happy to know that I was taking care of you. I feel I want to protect you and cherish you.”

 

“Oh, Jack you are so like him. Not only your looks but also how you think. I love you my darling.”

 

I felt a thrill run through my body when she called me her darling. I kissed her again. Her eyes shone. The tears had gone and I could feel her happiness.

 

When we broke apart, she went and cooked supper. Just a steak with a tomato and cucumber salad washed down with an ice-cold beer.

 

I told her about the job I had found. She was surprised that it had taken so little time. I could sense her relief that she would not have to triple shift to support us. When I told her how much I would be getting her jaw dropped. Then I told her that I had planned to give her half of my pay so she would not have to work so hard. She started crying again telling me that was not necessary and that I did not owe her anything.

 

“Kathy for lack of a better term you are now my girlfriend. If it were possible I would marry you. I never want you to suffer what you have suffered, ever again.”

 

“You would marry me?”

 

“Yes sweetheart I would, and if things work out I will. I love you very deeply.”

 

This released another flood of tears, but I could tell they were tears of happiness. She came and sat on my lap and we cuddled and kissed. We were still both naked and I could feel the stickiness of our combined secretions. I took her hand, led her up the stairs and into the bathroom.

 

I turned on the shower, adjusted the water and we both stepped in under the stream of water. I took shampoo and washed her hair, running my fingers through it. Then I soaped her torso and her tits. They were firm and stood high with pebble hard nipples, which I pinched and played with until she was moaning with pleasure. My hands soaped and caressed her from head to foot paying particular attention to her private charms, which I was exploring for the first time. She washed me as thoroughly with a large smile on her face.

 

Drying her, I carried her to her bedroom wrapped in a large bath towel. I bounced her on the bed delighted by her little girl giggles. I then sat behind her and combed her long hair until it shone and cascaded across her shoulders.

 

“Jack, I am so happy, but we need to talk.”

 

“Sure about what?”

 

“I want to be sure about you. You already know that I am bisexual and like women. I also love sex. Occasionally, I will be with other men. The way I feel now is that I don’t want to lose you ever, and I am worried about what will happen if I lead the lifestyle I led with your father.”

 

“Kathy, all I want is your happiness. If you need to have sex with others, be they male or female, I can understand. I know that lust and love differ. I want you to love me and no other. I can live with the situation, but would prefer to share with you those situations. Would that be possible?”

 

“Oh, Jack that is what I meant. I do not want you ever to doubt my love or to feel cheated. Now there is one other thing I need from you before they get here.”

 

“What is that love?”

 

“Please eat my pussy. I long to feel your tongue in and on me.”

 

I pulled her across the bed and spread her delicious thighs apart. She drew her legs...

To continue reading this story you must be a member.

Join Now
Published 
Written by ChrisM
Loved the story?
Show your appreciation by tipping the author!

Get Free access to these great features

  • Create your own custom Profile
  • Share your erotic stories with the community
  • Curate your own reading list and follow authors
  • Enter exclusive competitions
  • Chat with like minded people
  • Tip your favourite authors

Comments