Road Trip Ch. 13

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Anal

Memories, marriage and more

Scorpius1945

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Author’s notes:

1. This is a work of fiction. The activities and practices described in this story are not necessarily either condoned or recommended. If you choose to do anything described in real life with real people you do so at your own risk.

2. All characters are fictional and any likeness to any living person is purely coincidental. The story is purely imaginary and, to the author’s knowledge, bears no relationship to any factual occurrence.

3. For those who haven’t yet read the previous chapters, I suggest you read them to provide context before continuing with this chapter.

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I lay next to Celeste, arms around my new wife’s body, after having made love to her for the first time as her husband. We kissed tenderly, the moon, just past full, rising into the cloudless sky over the ocean, tiny waves lapping gently against the shore. It was such a beautiful location, this clothing optional beach we had chosen for the night, so peaceful. We kissed, then we were re-joined by Margarite, who snuggled in alongside me, kissing and cuddling us both.

“That was very sweet and loving to watch,” Margarite said, “I’m so pleased that you guys have allowed me to join your family. Thank you, darlings.”

We both kissed her, trying to ensure that even though she was not and could never be part of our marriage union, she knew that she was a treasured, loving and loved partner to us both. It hadn’t always been that way, however . . . .

My mind drifted back in time as Celeste cuddled into me and soon her breathing told me she was deeply and contentedly asleep. I remembered the strife we’d had together as Margarite insinuated herself into our relationship, trying to split us apart until we’d managed to rearrange ourselves, our feelings and, at last, our egos to accommodate her presence and her love for us both. I remembered how Celeste had punished her, cutting up her ass with a cane, the results of which were still visible four months later. Margarite had acted as though that was the inevitable price to pay for entry into our relationship, and she appeared happy and grateful that it was all it had cost her.

She had joined Celeste in her business as a call girl and prostitute, my bedroom becoming her bedroom as she entertained clients in our home. This worked well as my work changed somewhat, the main focus becoming the deflowering of 18-year-old virgins. A tough job, but someone had to do it. This was invariably done in the home of the girl and was usually arranged by the girl’s parents or mother. Very often the mother had a fear of her beloved daughter being brutally introduced into her sexual life by an unfeeling, uncaring and usually temporary boyfriend. Far better, they realized, to have a sensitive, caring, experienced male to do the introduction, especially as the male in question would never talk of the event and never try to foist his presence on the family after the deed was done. I smiled to myself as I remembered that it didn’t always follow the usual game plan.

I’d been booked by Eliza to deflower Sam, her daughter, two days after her 18th birthday. I arrived at the door at the appointed time, thinking this was a great way to spend my Saturday night, and was greeted by Eliza, a stunningly beautiful woman who was informally dressed in a wrap around gown. Her blonde hair tumbled in ringlets around her neck and down the front to just cover the swell of her breasts.

“You must be Hank,” she said before I had time to introduce myself, “Come on in. Sam’s been on tenterhooks all evening waiting for you to come.” She smiled at her very obvious pun as she stepped aside and ushered me through, leaning forward slightly as I passed her so I had to rub my arm against her breasts. She indicated for me to enter the lounge, which I did, and a younger version of Eliza stood from where she was seated on the sofa.

“Hi, Hank, I’m Sam,” she said, holding out her hand, which I took in mine, noticing the softness of her pampered skin. She grasped my hand and pulled me to her, embracing me and kissing me sweetly and sexily on the lips.

“Oh, I can see you two will get along just fine,” said Eliza, beaming. “I’ll make you some lemonade and let you get acquainted.”

Sam drew me towards the sofa and pushed me gently to sit down, then she sat on my knee, cuddling her warm, soft body, wrapped in a similar gown to her mother, into mine. This family is certainly not shy in welcoming a stranger, I thought as she leant forward for another kiss, her hand placing mine on her breast as she sighed into my mouth in obvious arousal. I could feel my cock hardening and pressing against her thigh; so could she.

“Is this for me?” she asked, moving her face from mine and looking downwards towards my rising trousers.

“Yes, Sam, all for you,” I managed to reply.

“Oh, goody. Can I unwrap it now, please?”

“If it’s what I think it is, you can wait until you’re in your bedroom,” said Eliza as she re-entered with the drinks. escort sincan Sam gave her a daughterly glare, then took two drinks for us from the tray, placed them on a side table, before continuing her seduction routine.

“For an 18-year-old virgin, you’re amazingly forward,” I commented, “Are you sure you’re still a virgin? Seems like you’ve got a pretty good routine going and I’ll bet mine is not the first knee you’ve sat on.”

Eliza answered before Sam could. “That’s the problem. She has a reputation as a cock teaser, which is very unfortunate because it means that guys shy away from her. Nobody even wants to be friendly towards her because she has a huge fear of sex, yet she wants it so bad. I was like that too, so it maybe runs in the family.”

“Mom!!” said Sam, glaring at Eliza, “Must you?”

“Yes, I must. Hank needs to know why his services are needed instead of you going out and losing your precious maidenhead like most girls do, in the back of a car or on a park bench. Remember, I’ve been there too so I know what it’s like. I also know that after my father took me in hand and did the deed in a loving manner, it was so much easier. You don’t have a father; he ran off with his secretary years ago and good riddance to the philandering sod, so Hank’s here in place of him, and he’ll do a damn side better job that Pete ever would. So just be grateful and be nice, and remember that tonight’s the night; no chickening out at the last minute this time.”

Sam hung her head after her Mom’s accusatory tirade, then she lay against me, snuggled her head against my neck and sobbed. I felt her soft body pressing against mine, racked by the sobs, and immediately felt sorry for these two women, so damaged and hurt by men, including the man who should have loved and cared for them. I made a vow that I would never leave Celeste like that, never leave a child of mine like that. I gently stroked her long blonde hair and held her tightly until she lay still. Then, with practiced resilience, she sat up and took a sip of her drink, as I did also. She smiled at me and leaned forward. Our lips met in a tender kiss, then the three of us began a more normal conversation, if such was possible while I sat with two gorgeous women, one on my knee, the other seated opposite me with her legs slightly apart, her gown spread enough to allow me to look up her bare inner thighs, almost, but not quite, to her pussy. My intent gaze was interrupted by Sam digging me in the ribs with her elbow.

“You’re here for me, not her,” she whispered into my ear.

My hand was still on her breast, where she held it, so I began moving my fingers, tracing the outline of her nipple, causing it to swell and harden so that its outline became visible through the thin fabric of her gown. She was obviously naked underneath, at least for the top half of her body. I started sliding my hand up her thigh, exploring as the fabric fell away to reveal her smooth, pale skin. She leant forward again and we kissed, longer, lasciviously, as my hand ventured higher. I felt her hand on my hard cock and also felt her ease her thighs apart a little more to provide better access. I glanced over her shoulder and saw her mom was slowly stroking her inner thigh through the gap in her gown, her tongue licking her lips as she watched us.

That timeless moment was broken by Sam pulling away from me, taking several gulps of her drink, then sliding off my knee and taking my hand.

“Come on, darling, time for you to come with me,” she grinned at me as she let the words sink in.

I gulped a few mouthfuls of drink then stood and together, hand in hand, she led me upstairs, followed by her mother’s eyes every step of the way. Once in her bedroom, she closed the door and locked it carefully, then leant against it and pulled me to her, my body pressing against hers as we kissed and caressed. We continued to kiss as she reached between us and unfastened my trousers, letting them slip down, followed by my undershorts. She held my cock in one hand, my balls in the other, and pushed her tongue into my mouth as far as it would go as I kicked off my clothing from around my ankles. My hands were on her breasts, massaging them, then I parted the gown and, reaching up, pulled the top off her shoulders and down her arms and back, baring her breasts. I leant backwards to examine my new discoveries, then played with them for a while, caressing them, watching the aureoles pucker with the cooler air, seeing the nipples harden. I squeezed both nipples quite hard and heard Sam’s sharp intake of breath as she pressed her pussy against my uncovered cock. She pressed her face into my shoulder and whispered in my ear.

“Please fuck me, darling, make me a woman; take my maidenhead now, honey.”

I could have just parted her gown and slipped my cock into her standing there, and if she’d not been a virgin, I would have. But the first time should be memorable and should be comfortably on her bed, so instead, I bent down and picked her up in my arms, walked the few steps to the bed and laid her down. She stared at ankara escort my cock, then reached out to touch it as I removed my shirt, standing before her naked.

“You’re gorgeous,” she said softly, “Hard, long, thick and wonderful. You won’t hurt me darling, will you?”

“There may be some discomfort but I’ll be gentle,” I reassured her, “Any discomfort will definitely be worth it in the long run, sweetheart.”

She smiled as I reached for the gown tie and slowly pulled it until the edges were free and fell apart, revealing her soft, warm skin with her breasts standing up proud and firm and her pussy sporting a tuft of hair, neatly trimmed more to reveal than conceal. My cock gave an involuntary lurch as I contemplated the task ahead. I lay on the bed alongside her, our hands roaming over each other’s bodies.

“Have you been this far before?” I asked softly.

“Yes, many times. It’s been at this stage that I’ve chickened out. On each occasion, as the guy’s been kissing me, as my body’s said ‘At last you’re going to do it’, I’ve leapt off the bed, held my clothing to my body, dressed and left the poor guy with a hard cock and nowhere to put it.” She looked away, obviously embarrassed by her revelation. “I won’t do it this time though, darling, so put him in me, blast that maidenhead aside and fuck me to womanhood.”

As tempted as I was to do just that, I knew that she’d have very unpleasant memories and maybe sexual difficulties for life if I followed her instructions. So instead I lifted her legs, spreading them wide apart and I knelt between them then lowered my face towards her pussy.

“What are you doing?” she asked, alarm in her voice.

“I’m going to eat you up,” I growled jokingly.

She caught on quickly. “Oh no, sir, please don’t eat me up, I’m much to young for that,” she replied in a high pitched, squeaky voice.

“Oh no you’re not,” I growled again, then licked her pouting lower lips with my tongue. “There now, doesn’t that feel good?”

“Oh, yes, that feels wonderful. Eat me some more please honey,” her voice normal again.

I did, sliding my tongue through her slit for a while before pushing it into her entrance. As I did this, I reached up and cupped her breasts with my hands, slipping her nipples between my fingers, massaging and squeezing them. I was rewarded by her soft moaning as she began rolling her head from side to side, her hips lifting her luscious pussy upwards for more attention.

After a while of this I slowly changed the pattern of my licking, bringing my tongue further forward to stroke it over the emerging nub of her clitoris. The first time it ran over, her body jolted and she let out a quick involuntary squeak, then she continued to moan and roll her head as before. After a few minutes I placed my lips over her clit and sucked it in, using my lips to massage her sensitive organ. She placed her hands behind my head and pulled me harder against her as her body began to writhe with the sensations. It took only a very few minutes of this before she gave a scream and her body thrashed in orgasm. I hung on as best I could and continued the stimulation until she showed signs of her release ending. I sat back and watched her as she opened her eyes and looked into mine.

“Mmmm, that was wonderful, thank you darling. You’re such a good lover, honey.”

“Why, thank you, Ma’am,” I replied with mock formality. “Have you had orgasms before?”

She looked away, then her gaze returned. “Yes, but only ones I gave myself,” she replied, then she blushed furiously. “And some I had when several of us girls had a sleepover,” she added. “Never with a guy though.”

“That’s fine. It doesn’t matter how you orgasm, it’s a natural way to please yourself, to be pleased by others and to please others. Don’t be concerned that having orgasms with women will make you a lesbian; it won’t, unless you want to be a lesbian. At worst it’ll be an occasional pleasure, at best you’ll be bisexual and will enjoy sexual relationships with people of either gender. My fiancée’s bisexual and really enjoys making love with both men and women.”

“You’re engaged? To be married? Yet you do this?”

“Sure, why not? Just because I make love with you doesn’t mean I can’t make love with my fiancée. It certainly doesn’t make me love her less. Actually, to tell the full story, I live with and love two women, who both love each other as well as me. It’s called polyamory and for us it’s working well, now. They’re both call girls as well, so have sex with other men. Maybe that seems weird, but it works for us.”

Sam lay there recovering from her orgasm, processing what she’d just learnt. Then she smiled at me.

“I guess that’s why you’re such a sexy and gentle lover, eh darling. Now, about that maidenhead . . . . .”

I felt between her legs; she was sopping wet, well and truly ready for the main event. I carefully slid a finger into her, slowly feeling for her hymen and found the barrier. I probed gently; it didn’t feel too substantial.

“You ready?”

“Yes, do it, now.”

I bent her etimesgut escort bayan knees up and spread them apart, then lay between them, taking my weight on my elbows as I worked my way up her body, kissing her stomach, chest, breasts, neck then lips as my cock head lodged in her entrance. She wriggled slightly, positioning it further inside.

“Do me, now.”

I did. I slid forward, felt the end of my cock press against the barrier, harder, harder, then with a popping sensation I slid into her virginal vagina. Sam was biting her lip, trying not to scream, as I remained still, waiting for the pain to lessen. Finally, she released her lip and smiled at me.

“I’m guessing I’m not a virgin anymore,” she said.

“That’s right. How was it?”

“I’m so pleased you did it. You’re so experienced it seemed easy and almost painless. Now, fuck me, cum in my cunt. Squirt your babymaking juices in me.”

“Are you on some form of contraception?” I asked.

“No, not yet.”

“Well, I need to wear a condom,” I replied, making to withdraw.

Sam held me to her tightly. “No, darling, Mom and I discussed this. She said the first time we’d take a chance, make like it was for real. That’s why we chose tonight; it’s not likely that I’ll become pregnant at this time in my cycle.”

“There’s always a possibility no matter what time in your cycle.”

“Yes, we know that and want to take that chance. It makes things a lot more real and exciting. So, fuck me, honey, you have tonight to make a baby in me; a once in a lifetime opportunity. If I do become pregnant tonight, I’ll have a lasting memory of you.” She grinned up at me, moving her hips to cause my cock to slide in and out slightly. I had to admit to myself that the thought that I could be fathering a child was very arousing, so, reassured slightly by her words and by the adage that the customer is always right, I continued.

Gradually I plowed deeper and deeper with successive thrusts, each thrust ending with my head pressed hard against the end of her vagina, each thrust causing her vagina to lengthen to better accommodate my cock, until at last I felt the base of my cock pressing against her clit. I stopped there, grinning down at her.

“You realize that I’m fully inside you, don’t you?” I asked.

“Yes, darling, and it feels wonderful. Please keep going, cum in me, impregnate me, squirt your juices in me, honey.”

Again my cock twitched, so I continued, fucking into her deeply, my fingers squeezing her nipples as she quickly became more aroused; then, with a scream, she came hard, her cunt spasming around my cock, squeezing it, trying to milk my cum. I relaxed and held off as she writhed in orgasm beneath me. Once she slowed down and her panting decreased, she opened her eyes and grinned up at me.

“Thank you, darling, now I need your juice in me. Cum inside me honey, fuck your slut hard, make a baby in me.”

She rolled me off onto my back and quickly straddled me, then sat down on me, engulfing my cock with her wet love tunnel. She sat back, her breasts standing out proudly from her chest, nipples hard with arousal as she began moving back and forth on my cock.

“For a virgin, you seem to be quite experienced,” I commented.

“You can thank porn sites for that,” she replied with a grin.

After a few more strokes she leant forward so her clit was stimulated, and very quickly she began panting again, her eyes tightly shut as she was once more transported to her private paradise. Her head went back, a guttural groan came from her as she came for a third time tonight. I was close, but managed to restrain my orgasm, knowing next time would probably be the time. She slowly collapsed forwards onto me and lay there, her heaving breasts pressed into my chest. After a short recovery time she grinned up at me again.

“What now?” she asked, “You still haven’t given me your cum.”

I rolled her off me onto all fours and positioned myself behind her. “Time for a bit of doggie style fucking, sweetheart.”

She lowered her shoulders to the bed, exposing her sloppy trench as I impaled her on my rigid pole. From this angle I went in deep and each of my first few thrusts were accompanied by a grunt as I bottomed out. I reached around her chest and cupped her swinging breasts, massaging them, squeezing them as I pumped myself to my orgasm, oblivious of her needs now. I felt my cum rising, getting ready to shoot into her unprotected sheath, ready to fertilize her unsuspecting egg, ready to make a baby in her from her first fuck. These thoughts pushed me towards my orgasm and with a final hard thrust I filled her cunt with my hot, potent sperm.

The feeling of my hot cum spurting from my pulsating cock must have pushed Sam over the edge as well as she moaned and shuddered on my cock, then slowly relaxed. After a few minutes we rolled sideways and lay spooned against each other. My cock softened and slipped out of her hole, followed by some red-colored cum as I held her gently. Over a period of a few minutes, she relaxed totally and became unresponsive, sleeping off the effects of her first sexual experience, including multiple orgasms, as a woman. I waited a while, then slipped out of bed, wiped myself in the bathroom, dressed and quietly left the room, turning off the light.

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