Girlfriend Agrees to Sex with his Buddies (First Cuckolding Book 8)

by Matt Coolomon

  “Yeah – that’s a very tight little starfish, Ang. Aw, yeah – that’s all the way in now…. You’ve got all of a nine inch cock up your arse, Ang. How’s that feel?”

  “Mmm – it feels deep!”

  “Ooh, yeah…. Taking your anal cherry, huh? This is really your first time?”

  “Uh huh. You’re the first man to take me like this, Stan…. Just slow, though, okay – deep and slow until I get used to it?”

  He stayed in deep and rolled his hips, humping her. “Like that?”

  “Uh huh….”

  “Hey, Jack,” he called over to the doorway. “You’ve been missing out not doing her like this, man.”

  Jack cleared his throat. “Yeah, I guess…. It’s not too painful, Ang?”

  “No – it’s okay. It isn’t hurting now. It just feels strange having it so far up me back there.” Stan ground against her, humping some more. “Mmm, especially when he does that.”

  She had twisted her body to be on her belly but with her bottom raised as he held her hips and continued humping her. He suddenly stopped, grinding deep into her and whispering into her hair, “I’m going to blow, Ang.”

  “Are you ready to?”

  He pulled back and bumped her.

  “Mmm – that’s nice,” she moaned.

  He pulled back and bumped her harder.

  “Uh huh…. Do it, Stan…. Cum in me really deep, okay?”

  He bumped her again, and again, and he started fucking her hard and fast, and suddenly he ploughed all the way up her and let out a deep groan, “Aw, yeah – mmm – mmm,” he cried. “Take that, baby…. Take that big fucking load,” he gasped.

  He collapsed over Angela’s back, pulling her onto her side and surging up against her bottom. His dick was still pulsing but it quickly softened and oozed out of her. It left her anus open and slick, and tingling blissfully. More pleasurable still, was being cuddled right then. She held his head upon her shoulder with her fingers in his hair.

  Jack was still there watching. She gave him a tiny wave.

  14

  Angela woke in the morning absolutely glowing. She expected to be a bit sore but her pussy was ready for more and her bottom was just slightly sensitive – her tiny back entrance tingling a little. She felt it curiously and found she was kind of slippery inside. Otherwise she was a mess down there – her inner thighs were sticky and felt yucky. She decided that another bath was in order.

  Stan was still sleeping. She slipped carefully from the bed and found her panties and negligee. She covered her front with the negligee and crept along to the main bedroom. The door was ajar. Tanya was sleeping. Wes was propped up in bed scrolling on his iPhone. He smiled.

  “I just have to get some things,” Angela whispered, and she tiptoed across the room to her open suitcase and fished out panties, a tank top and denim shorts. She took her toiletries bag from that bathroom and grabbed a fresh towel, dropping her nightwear into the wash basket.

  She tiptoed back through the bedroom with her clothing and bag clutched in one hand and covering her genitals, and the folded towel in the other hand. Wes was blatantly looking at her tits. She blushed as he glanced up, and she peered back over her shoulder at him checking out her bare bottom as she left the room.

  Paul was asleep in the next room. She peeped in on him. Jack was in the next one, sleeping soundly. She left the main door to the bathroom ajar to invite visitors to brush teeth or shave or whatever. She ran her bath and quickly used the toilet, cringing at the sound of the flush in the big quiet house. She peeped into the two adjoining rooms and saw that both Stan and Jack were still out to it. Jack’s room was very dark. He could well sleep until lunchtime, she thought.

  She made the water scolding hot and soaked until the skin of her fingers wrinkled. By then she had shaved her legs and pussy and otherwise refreshed, feeling squeaky clean on the outside and flushed and ready for more servicing by the men on the inside. Her three love bites had already darkened, she noticed in the mirror. Her white, lace-trim tank top covered the ones on her breasts. It was quite low cut beneath her arms, allowing her boobs to bulge a little there, but the bite mark on the side was just concealed. It was a tight fitting top but loosely woven. It hugged her boobs and showed off their fully rounded, slightly drooping shape with her small, dark, high-set nipples distinguishable now that she had pinched them and made them firm. She giggled at herself – such a tease all of a sudden – although she was planning to make the guys work a bit harder to get at her with the jean shorts on today. They were also tight fitting and there’s no way any of them would be getting their hand down the front without undoing the zip.

  She checked her butt in the mirror. This was suddenly a highly interesting asset. She had always been proud of how firm and tight her bottom was – thanks to a well-used gym membership. She had always considered her derriere to be kind of sexy. Today, she looked at it in the light of it being a potential sex zone for the men. She could use her hand and her mouth. She had plenty of practice bringing Jack off with hand jobs and occasionally sucking him off too. She had an attractive pussy. She liked it. Her outer labia were smallish and didn’t protrude, hardly at all. Shaved as she was, her pussy was a perfect slit – her vulva smooth, and with her slender thighs presenting a gap the width of maybe three big rough fingers, it was two delicate mounds split and presenting a hint of pink flesh between. From behind her slit was more of a gash. She stretched a cheek and noticed how her inner folds were particularly reddened. She wasn’t sore at all, but all of the sex yesterday had her labia enflamed. Her back entrance did kind of resemble a tiny starfish, she considered, giggling to herself at the silly thought. Along with her hands, mouth and pussy, she suddenly felt she had another sex object to offer a man – one that would be nice and tight around his cock to provide him with extra stimulation, and as with traditional sex, it also allowed him to hold her and press his body against her, which she absolutely loved.

  Angela pulled her shorts back up after having tugged them down for a quick inspection of her lower-body sex objects – both of them! She would be teasing guys a lot more with her bottom from now on.

  No one had woken yet. Mark was sound asleep on the lounge. Angela made up a huge batch of pancake mix ready for the guys, and she brewed coffee, the lovely aroma of that should wake a few of them, she expected.

  Missy was waiting for her breakfast, her tail thumping the ground. Angela let her off for a run around the yard for a while. Rexy next door was on his chain, so she would be safe from him. It must have been too early for Mr. Peters to be spying yet. His chair was empty, his house closed up tight. There were bugs and leaves to skim from the pool and the filter needed cleaning. These were familiar jobs for Angela, her uncle had her well trained to look after his house.

  She got to thinking about that. He was getting more and more involved in his art exhibitions and travelling away to all sorts of seminars and functions. He had mentioned to her jokingly more than once that she should just move in. She had never given that idea any serious consideration because she had been focused on setting a date and getting married as soon as possible after Jack finished college. She wondered about that, though. Perhaps they didn’t need to rush anything. Jack had a self-contained apartment at his parent’s house. There was no way Angela could ever live there with him, but she didn’t mind staying over sometimes. Why did they need to rush when a couple of years with them both working and living rent free would mean a great start financially? As it was, they had nothing saved and a big college debt between them. Angela, being only a year out of college herself, still owed plenty for her tuition.

  Her uncle joked that he wouldn’t have to cook if she was there, but he was a terrible cook and Angela loved the kitchen – no problem there. She wondered about Vera – how that worked. Vera never visited when Angela was staying. She had a house of her own across town. Then there was work – it was about a fifteen minute drive, but her house was ten minutes in the other direction, so it was
virtually the same commuting time. And living at home with her strict, conservative parents was not particularly fun. It was fine, but nothing she was going to miss when she moved out.

  The only other consideration was Tanya. Angela loved hanging out with her little sister. They were inseparable when they were home together. Of course, if Angela was to get married that would be over, anyway. It was destined to end soon no matter what.

  “Hmm – I wonder what you would say for real, Uncle Mike,” she said to Missy, rubbing the dog’s ears and stealing her rope toy to toss down the back of the yard. Missy was back in about two seconds. “Do you want me to come and make your dinners, Missy? Just us girls and weird old Uncle Mike.” Her uncle had never made her feel uncomfortable at all. He never looked at her in an inappropriate way. He was kind and gentlemanly. In spite of the freaky porno clips, Angela had no reservations of that kind about living under his roof.

  Mark came outside, stretching. He had swimmers on. “Hi, Ang!”

  “Hi, Mark, Are you going in?”

  “Yep…. Need some exercise.” He dived into the pool and started swimming laps. Angela watched him for a while, admiring his lithe, muscular body. Her belly was tingling in anticipation of having him between her legs next time. She had decided she wanted to experience his big fat cock in the missionary position. She had thought about that when lying cuddled up in bed with Stan last night, and was looking forward to trying it.

  She went in to check for breakfast orders. Jack and Stan were chatting over the breakfast counter with coffees. Angela leaned over and kissed Jack. “Good morning. I didn’t expect you to be up yet in that dark room.”

  “I know.” He yawned. “I might go back to bed for another couple of hours, but I’m too hungry to sleep.”

  “Pancakes?” Angela asked cheerfully.

  He smiled. “Perfect.”

  “And hello, you!” she said to Stan. “That was interesting last night.”

  “I know…. Sorry I crashed right after. I don’t remember going to sleep, but it was pretty quick afterward.”

  He kissed Angela’s lips softly, taking hold of her hips. She willingly turned and pressed her bottom back against him. He pulled her close and she arched her back, lifting to tiptoes and peering back at him. He looked down at her bottom, grinning. “Are you sore back there at all this morning?” he asked.

  “No – not sore – just kind of tingly and still a little bit wet and slippery.” She blushed, glancing at Jack as well. “And he was watching, weren’t you, Jack?”

  “Yeah – I couldn’t see much. So, that was anal, eh?”

  “Uh huh,” Angela uttered, wiggling back against Stan. “My first time ever, and I hope not my last.”

  Stan smoothed up over her belly and squeezed her tits. She opened to accept his tongue in her mouth with a deeper kiss that time. She continued to wiggle and squirm back against him. His cock was firm and between the cheeks of her bottom.

  “Stan’s thingy isn’t as thick as yours, Jack. It’s longer but kind of slender…. It didn’t feel like it was stretching me too much…. I wouldn’t be able to let Mark have me like that either. Maybe it would be alright with Paul.”

  “I’m happy taking care of that end of things,” Stan chuckled. “This end,” he added, giving Angela’s bottom a pat. “I’d be happy to oblige again later.”

  “Mmm – you had better be!” Angela teased. “I definitely want to try that again while we’re doing free love.”

  “So – nine inches, eh, Stan?” Jack asked disbelievingly.

  Stan chuckled. “Well, give or take an inch – maybe nine along the bottom if you allow some of the support structure under there.”

  “It felt like ten inches to me,” Angela declared.

  “It didn’t hurt, sweetheart?” Jack asked warmly.

  “No – it felt strange at first. It was a long way inside me back there. But then I got used to it.”

  Stan slipped a hand up her top and felt her tits bare. “She stayed nice and tight all the way. You should let Jack try it occasionally, Ang. If you work her open with a finger and then your thumb – do some licking…. It shouldn’t hurt with enough preparation. But not too often, otherwise she’ll get stretched and won’t be as tight anymore.”

  “Mmm – and I want to stay tight,” Angela cooed. She recalled her thoughts from the bathroom earlier, about having something different to offer a man. If she lost that tightness, it would be gone – wasted.

  “I remember Jolene used to always have love bites,” Jack mentioned.

  “Oh, yeah – I get carried away sometimes. Sorry, dude.” Stan grinned in reply.

  “I’ll have to blend it with makeup if it’s still there when I go back to work. The kids will tease me about that for sure.” Angela giggled. “And he did these ones too,” she went on, lifting her shirt and showing them her breasts. Stan was still feeling her up. They had a look at the bite on the underside of her left breast. He pulled her right breast across as they checked out that mark as well. “At least those will be covered by my clothes,” she said, meeting Jack’s gaze and smiling through her blush.

  She left her top pulled up. Stan felt both of her tits, gripping them and squeezing her nipples with his thumbs and forefingers. She turned her head, lifting to accept another deep tongue kiss. He popped the stud and lowered the zip on her jean shorts. “Uh oh,” she giggled, and she looked to Jack.

  Jack was sitting on a stool in his boxer shorts and an open robe. He felt his cock through his shorts. Angela looked up from there and met his eyes with a smile. “Mmm – this is interesting,” she cooed as Stan wormed his hand down the back of her shorts and panties. He hadn’t lowered them, so he didn’t have much room. She leaned over the counter and kissed Jack, moaning into his mouth as her anus was poked by a fingertip. Stan rolled his finger around the rim of her tiny entrance. The tip slipped inside of her, then he rubbed around from within, oh so gently until he had inserted to the second knuckle.

  Angela felt her anus getting slippery. Her pussy was too. Stan’s index and ring fingers were inadvertently poking into her slit while he worked his middle finger in and out of her bottom until he had inserted the full length of it. Angela lifted again, keeping her back arched and her hips tilted forward, Stan held her chin and stuck his tongue into her mouth. He kept his finger fully embedded in her and just jiggled his hand, effectively fucking her with it. He slipped his other hand down the front of her panties and worked her clit. Within a minute of that she had a small orgasm, her body pulsing in mild little quakes that were resonating from her belly and making her bare tits tremble.

  Stan carefully extracted his digit. It slid out easily. She felt that her anus was very wet and slippery. He used the moisture he had drawn from her and rubbed around her puckering little hole. As he kissed her deeply again, he inserted the tips of two fingers and worked the tension in her clenched sphincter. It was tingling like crazy – the gushing pleasure of her orgasm extending back there.

  He withdrew and gently rubbed her for a moment longer before removing his hand from down the back of her pants.

  Angela zipped up, her face flushed as she looked to Jack again. “So – pancakes?” she asked cheerily.

  15

  After all the men had been fed that morning, Angela and her little sister went for a swim together, peacefully for a while, and then the guys all gravitated outside. There was a hoop mounted on the garage over the far side of the yard and they played basketball, still not bothering the girls.

  “There’s Mr. double D now,” Tanya said.

  “Good morning, ladies,” he called over the fence.

  “Hi!” they both returned with smiles.

  “Why don’t you come over for a swim, Mr. Peters?” Angela asked.

  “Oh, I wouldn’t want to crash your party,” he chuckled, motioning to the guys.

  “Pft…. Don’t worry about them. You’re very welcome. Isn’t he, Tan?”

  “Yeah, of course! Come over, Mr. D.”
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  He chuckled again. “Okay, I’ll come over and check on Mike’s orchids…. It’s not anywhere close to swimming weather for me, though. You girls are brave ones.”

  There was a gate in the fence down the back next to Missy’s dog house. Uncle Mike had an extensive flower garden that was very well tended, as had Mr. Peters for that matter. Perhaps they were in friendly competition, Angela guessed – friendly enough that Mr. Peters needed to fuss around down there pulling weeds and checking sprinkler settings for a while before he strolled over and sat in a chair by the pool.

  “Don’t worry – Mr. D is used to nudity, Tan,” Angela said as she pulled the strings and removed her bikini top.

  “Oh, yeah – I noticed.” Tanya pulled the strings on her top too.

  The girls hooked arms over the edge of the pool beside where the grinning old neighbour was sitting.

  “No, I mean naturalist outdoor nudity,” Angela told her sister. “Aren’t you, Mr. D?” The handle Mr. D suddenly suited him, Angela decided. “He’s an old naturalist from way back.”

  “True. True. But this is better,” he chuckled. “It’s rare we get to ogle firm young titties like those ones.”

  Angela grabbed a small beach ball that was floating around. “You go over there,” she told her sister, and the girls swam to opposite ends of the waist deep pool. “Catch, Mr. D!” Angela called and tossed him the ball.

  He caught it and tossed it to Tanya. She had to jump to catch it, her little tits jiggling proudly. Angela stood to catch the ball too, and she remained standing as she tossed it back to Tanya. The childish game went on with Mr. Peters playing along and watching their tits as they giggled and lunged around to catch the ball and toss it. The guys were looking over. It was just the four of them playing basketball. Jack was asleep upstairs.

  The girls both lunged for the ball and ended up together. Mr. Peters was waving a hello to the guys. “Should we take our pants off for him too?” Angela whispered to her little sister.