High School Dates Ch. 16

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"Under her dress? Me?" Katie's brother asked.

"That's who she asked to do this." The photographer said with a grin on her face. I shook my head and followed directions. It didn't take long to realize what was in play. That secret Betsy had told me about, this was where it was happening. As soon as we had her in the air, Mandy stepped forward and pulled the wedding dress up and tucked it across her waist, exposing her from the waist down, exposing that all she had on were her white stockings, white heels and one white garter high on her thigh. Her pussy was freshly shaved bare, glistening with wetness in the sunlight.

"Okay lover. Drop em and give me that cock. You've been dying to have sex without a condom for the last year, well, here it is. Come fill me up and make us a baby!"

Chris looked around and then grinned and nodded. He stepped in front of her and let his pants drop and then pulled out his already hard dick. I'd seen him have sex with her and with Betsy plenty of times, but this was different. He stepped in front of his bride and we lowered her down, both Eric and me dropping to one knee to get her at the right height. This time he took her much more gently than I'd ever seen him do it before. There was no rushing, but there didn't need to be. You could see it in both of their faces as he started to slide in and out of her, his cock teasing her insides, drawing moans and gasps from her, as his engorged shaft slid in and out of her.

"That's it, lover. Make me come! Oh God make me come. Give me your cum, fill me up and give me a baby!" she moaned loudly as her legs began to tremble. I held her up and spread for him as he pumped his hips in and out, sliding his engorged head into her spasming pussy. He groaned softly as his cock swelled inside her.

"Ohhhhh fuck." He groaned as he jerked and pumped shot after shot of cum into her. The photographer got close and took shots of him inside her, then slipping out of her, and then his cum leaking from her and dripping to the ground, as her body continued to shudder and tremble in her first married orgasm. It wasn't at all what I would have expected in a wedding photo shoot, but I understood Katie enough by now to know why she would want something like this.

The downside is that it had me SERIOUSLY turned on. So much so that there was a significant bulge in the front of my trousers, a sight that the middle-aged female photographer didn't miss, as she stood almost between my legs to get her downward angle shots at Katie's pussy. "You were right." She said to Katie as she looked around at all the guys, and even one of the bridesmaids holding her dress up in front and fingering her bare pussy.

"Told you." Katie answered, as Eric and I gently set her down and let her dress fall down over her mostly nude lower half. "You girls know what to do!"

"We do." The one called Sylvia said as she took Eric's hand and pulled him gently away from where he stood near his sister. "We can't have you boys showing up at the reception looking like this. It wouldn't be proper."

"So, what do you want us to do about it?"

She grinned at Eric and reached behind herself. In moments her dress was sliding down her body, leaving her completely naked except for her high heels. "How about you fuck me. That should take care of it."

"But my wife..."

"Will never know." She said as she reached for his pants and started to undo them. "I suppose, if you really didn't want to, I could suck you off, but then it wouldn't be very gentlemanly to leave me hanging, now would it?"

"I...um...I don't have any condoms." He finally croaked out.

"Who said I needed you to wear one?" she said as she pushed his briefs down and exposed his rock-hard shaft. She started to stroke it and then turned herself around to face away from him. She bent over and guided his cock to her waiting pussy.

"Oh damn." He groaned as she rubbed his head up and down her clearly wet lips, spreading her juices over his engorged head. She settled him into the opening to her depths and pushed back at him, forcing his head into her a couple inches. "Ohhhhhh fuck." He groaned again as he reached for her hips and held them, pushing himself deeper into her.

I felt a hand on my arm and looked to my right, finding Mandy standing next to me, as naked as Sylvia. "As the Matron of Honor, I get the honor of taking care of the best man." She said quietly.

"You do?"

"I do." She answered. "But if you don't want me to, I understand. Jeanie, the photographer has agreed to take you if you'd rather not do it with me."

"God knows I want to." I answered her honestly, "but I'm afraid to. I'm afraid of what it might start." I whispered.

She nodded sadly and held a hand out to Jeanie, who was standing nearby. She pulled Jeanie toward me, and put her hand in mine and then started to back away. I pulled my hand away from Jeanie and grabbed Mandy's hand, pulling her back. "Maybe if, it wasn't just you and me, it might be alright?"

Her face brightened with a wide smile. "I think that might be alright. But then maybe we better undress Jeanie?"

"I think I can handle that."

"In the meantime, maybe she can get your hardon freed up?" Mandy asked with that wicked little grin that I loved so much.

"You're really gonna have sex with both of us?" The photographer asked in surprise.

"Trust me, he can handle it." I heard Katie answer from behind me as her hand pressed to my back. "I've seen him take care of three at once."

Jeanie raised her eyebrows, but let Mandy undo the button-down blouse she had on. Jeanie wasn't a bad looking woman. She was maybe early forties, not slender, but not particularly fat either. She had a large chest, which Mandy soon had exposed, with large round brown areola on the front of each double or triple D teardrop. She had small hands, which seemed to be unable to grasp her fingers all the way around my shaft, and a fairly large triangular shaped mat of hair on her mound and between her legs. Her hand stroked my dick slowly as Mandy knelt in front of her to help her take her pants and underwear off and then stood up; the two of them, now naked, in front of me. Mandy wrapped an arm around Jeanie and pulled her toward me as she too stepped up to press her nude body against mine.

I reached down to both their crotches as the two of them took turns kissing me, Mandy very lovingly and Jeanie with an almost aggressive desire. I let my fingers tease both of their wet pussies, working my middle finger between their lips. I heard moaning and grunting around me as the other groomsmen fucked their respective bridesmaids, and then heard the familiar sound of Katie grunting as she did when she was being fucked from behind.

"Who do you want to come in?" Mandy whispered to me. "You can have either of us."

"Do you have to ask?"

"I was hoping you'd say that." She whispered before kissing my cheek. She turned to look at Jeanie. "He's all yours, just leave enough for me to get a turn."

"You really do mean it? You want me to fuck him?" She asked, still apparently unsure.

"Not very fair for us to all do this in front of you and not include you, is it?" Mandy asked with a soft, feminine chuckle I'd heard so many times. "Not quite as much fun as getting to lay down, since we don't want grass stains on their pants, but I've found letting him take you from behind actually lets him get so deep it feels like he's pushing all the way into your belly."

"Well, what the hell," she said with a smile. Jeanie pulled away from me and turned, to put her back towards me. Her fat, meaty outer lips, that hid almost all of her delicate inner lips, pushed out at me from between her thighs. Mandy grasped my cock and aimed it at the pussy in front of me, as she coaxed me to move closer with gentle pressure on my dick. I watched her rub it up and down Jeanie's pussy lips and then settle my mushroom head into the entrance to her vaginal tunnel.

She let go of my cock and moved behind me, pressing her hips to my bare ass and her tits to my back. She leaned her face near mine and pressed herself against me, forcing, slowly, into Jeanie as Mandy whispered in my ear. "As soon as you make her come, you can do this to me."

"Yeah." I agreed breathlessly, reaching for Jeanie's hips and pulling us together. Mandy stepped back, while I started to stroke in and out of Jeanie, pumping my cock deep into her with each thrust. I could feel her tight confines expand with each stroke to accept all of me, both girth and length, drawing moans and gasps from her each time I pushed into her. In and out I thrust, concentrating on drawing Jeanie's already growing orgasm, to its full potential. I leaned part way over her back and reached down for each wildly swinging breast, working my hands down each massive orb until I could cup them, letting her large rock-hard nipples protrude between my fingers. In and out I thrust, squeezing her now captured tits, and her nipples at the same time. Over and over, she moaned how good it felt, and how she was going to come. I shifted my angle just a little, squatting lower so that my head pushed along her tunnel wall a little bit harder, drawing more gasps and moans from her.

"Oh God! I'm gonna come! I'm gonna come so fucking hard!" She moaned as her legs started to tremble. I felt a hand between my legs and realized that Mandy had put her hand on Jeanie's pussy from behind me. Her finger stroked Jeanie's clit, pushing her over the edge to fall down into orgasmic bliss. Her whole body shuddered and jerked as she came, Mandy thankfully capturing the copious flow coming from her so it didn't spray out all over the pants still around my ankles. I thrust in and out of her as she climaxed, pushing it even higher, until finally she reached back and pushed my hip back. "Enough. Oh God, enough for now, please."

"Then it's my turn!" Mandy said, pulling her wet hand from between Jeanie's legs. "Good thing I decided to play with her or you might have ended up with wet pants."

"I'm sure I would have." I answered as I stepped back and pulled Mandy toward me. She started to pull away but I stopped her by circling my arm around her waist. "No. Don't. Let me see your face while we do it."

She nodded. "I'd like that too." She whispered. "But you better take off more clothes then."

"Do I need to?"

"Oh yeah." She said, as she turned to find Katie and Chris standing nearby, kissing. "Katie, I think he needs to lose some more clothes."

"He does?"

"Yeah. Trust me."

"Well, I know what to do about that. Girls?" She said, "strip him!" In moments I was surrounded by three girls, not counting Mandy, my tux being pulled off item by item until I was as naked as Mandy.

"I hope they plan on helping me dress again." I joked.

"I have a hunch that can be arranged." Mandy asked. "Now." She said, stepping toward me and pressing her big, firm breasts into my chest. I could tell they were warm and must have been full of milk like the night before.

I reached down and lifted one leg while she slipped a hand between us to find my dick. She guided me between her legs and rubbed my already lubricated head between her warm wet lips. I groaned softly as she arched her back and pushed herself down my shaft. "I'm sorry I'm not tighter." She whispered as she moved her hands to my shoulders to balance herself.

"Do you guys always have sex in front of other people?" Jeanie asked quietly.

"Oh, most of us have a history of it, from high school days." Katie answered with a laugh. "Trust me, it'll be just fine."

I tuned out the fact that I was fucking in public, my mind focusing on Mandy and the resurgence of emotions that were flooding me. I started stroking in and out of her, pushing up into her with each stroke. I was already pretty damn close to a climax from fucking Jeanie, and what I was feeling welling up in me was pushing me ever closer.

"Oh God David, I missed this so much!" She practically whimpered as I thrust up it her. I stroked both of us along the slope up to climax, her body responding. I suddenly felt a wetness on my chest and looked down. I could see Mandy's tits inches from my chest, her nipples spraying little white streams of her milk out onto my chest. I felt her legs against mine, trembling as she started to climax around my plunging shaft.

"Oh damn." I groaned as her body shuddered and squeezed her pussy around my shaft. I slowed my strokes, wanting to draw this out as long as possible, but could only hold my urgency at bay for a few more seconds. I let my arm pull us tightly together, her tits pressed to my chest as my cock began to surge into her. I felt my cum flowing strongly up into her, her body jerking and a gush of her juices running down my legs a she climaxed fully around my shaft. We stood there, panting and jerking in each other's arms, for almost two minutes before I finally let her leg down and my softened cock slipped from her.

"Now that's what I call an intense fuck." One of the girls said as I looked down at Mandy's face.

"Yes, I'd call it one too." Mandy whispered, just barely loud enough for me to hear her. "Thank you, David. I know it'll be the last time, but thank you."

"Yeah. I know what you mean." I answered in an equally quiet whisper. "Thank you for this. Somehow, I have a feeling you were behind all this."

"I was, with Katie's help and approval of course. We knew you wouldn't turn me down this way." She said with a smile. She turned her head to look at Katie. "Thank you."

"My pleasure." Katie answered. "Alright girls. Our best man needs to be dressed and I happen to know he responds much better to a naked woman than a dressed one, if you catch my drift?"

They apparently did. It took about five minutes for them to get me completely dressed, with even Jeanie helping out. She and the other girls then dressed and we all headed back to the limo, and what should be the reception, nearly ready to start. I couldn't help but notice that almost all the guys had their hands between the legs of their bridesmaids, now knowing that they were all panty less and more than willing to have sex.

The reception was pretty much what one would expect. None of the shenanigans that took place on the photo shoot were happening here, thankfully. Though I did notice that once the official portions were done, a couple of the wedding party disappeared for short periods of time, well, long enough to have a quickie anyway.

Betsy and I enjoyed hours of dancing together, and with friends on occasions. I even got to dance with the bride herself for a short time. It was a most enjoyable reception and when we got home, Betsy and I talked a long time about how it felt to be intimate with Mandy again. Then we made love, for the first time ever, having a barrier between us as we did. It would be a hard few months, for both of us, neither of us enjoying the loss of sensations; but, it was the price we would pay to have the chance to make our 'first life' together on the day we formally start life together.

12
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servant111servant1117 months ago

This whole thing just dropped into the cuckold zone... Sad because it was a really excellent tale before this,.. Now you have this naked wedding photo shoot orgy and frankly this is one of the most pathetic debauched messes I have ever come across. Publicly impregnating his wife with their first child in a wedding orgy strikes to the heart of the marriage concept. There is NO love here just pornea...ie using others as tools to gratify their momentary lust impulses. Just sick and sad.

2 stars

RsHmarRsHmar9 months ago

Pretty good story with lot of hot sex scenes ,but can't read this anymore . There's no loyalty. And I'm not really liking cuckold David .

LacastrianLacastrian12 months ago

"It took a little getting used to, seeing another guy between Betsy's legs; but, as long as we were using condoms, I had gotten used to it" why the hell is this cuckold story in the romance category?

AnonymousAnonymous12 months ago

As some other readers have pointed this story is in the wrong category. It fits much better in loving wives or Group sex.

AnonymousAnonymousabout 1 year ago

The story never ends. But it is the same, over and over again. He an Betsy should just be together with each other. (Maybe his mother also, but no one else.) The story is getting monotonous.

AnonymousAnonymousabout 1 year ago

Goof story. I think i know what Mandy has planed have sex with David one time and hope she get pregnant with his baby so she can her husband and his family to fuck them srlfs as she puts sn end to her marrige snd moves back home and raise her daughter and David'd baby. David should take the woman who took pictures and show her what he can do when no one else is around. I dont his marrige yo Besty will last. I have a feel she will find someone at work to fuck her and she will end up pregnant and breaks David's heart which David to make up with Patty and marry her

OkieDokeDudeOkieDokeDudeabout 1 year ago

What the heck? About the time I think he’s grown a back bone and decided to commit to ONE woman he’s back with the one he said he’d never be back with? And Betsy just says it’s ok? Nope. I’m done. He has shown he will have sex with any woman just about any time and any where - even the ones that stab him in the back. I love nearly all of the stoyman’s stories, but I can’t get behind this one any longer.

AnonymousAnonymousabout 1 year ago

The shark has been jumped.

Don't see how this can be continued with any sort of believably "real" characters.

MehntalityMehntalityabout 1 year ago

I've got to admit, I find myself agreeing with Aardie... The more this story advances, the less I like the direction its going. The MC is becoming less likeable with each chapter; he has no moral compass when it comes to sex, he has no willpower, no backbone, and is manipulated by nearly every woman in his life who are also very unlikeable.

.

He says he would be fine with monogamy but his fiance won't let him try...he was talked into swinging even when he was not sure about sharing his girl with other guys. His grand gesture of turning down Mandy was quickly erased the next day when he was asked again, this time with peer pressure. (Don't get me started on how he left Mandy half naked on her own in the park when he "boldly" walked away from her. Didn't wait for her to get dressed? Didnt care about a possible rape scenario?)

.

It says alot about how unlikeable I find these characters that I was immediately suspicious about Betsy and Katie's motives about wanting to get pregnant so soon after the bachelorette party where 'supposedly' no sex occurred. Makes me think its another Mandy situation but they want to hide the possible pregnancy by making their partner think its theirs? It doesn't seem at all out of character to me.

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Lastly, on the topic of swinging...its only swinging if they do it as a couple, both parties present at the location the sex is taking place. Having sex without the partner around is called an open relationship. Also, I lived through the 80s as well...most swingers at that time were older folks in their 30s-50s who had actually experienced the 'free love' hippy lifestyle of the 60s, not teenagers who weren't born or were toddlers during that era. Maybe some of the hippies children dabbled but it was definitely not normal for every girl or couple to be onboard with partner sharing. (They pressured Katies brother to cheat on his wife and she was fine having sex with her brother there?) In fact, monogamy got a huge surge in the hetero communities with the rise of HIV and AIDs. I only bring this up as the author specifically prefaced the era as an explanation of the sexual attitudes of the characters.

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I'm invested enough to want to know how all this ends, but I'm definitely not enjoying the ride as much as I was with the first chapter.

muskyboymuskyboyabout 1 year ago

Not a romance as there are no likeable characters. Nothing but women manipulating horny, mindless men.

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