My Stepmom's Boyfriend

by Cassandra Dee

  Suddenly, Caitlin’s phone buzzes on the table. Without missing a beat, she silences it and digs back into her gyro while letting out another ecstatic moan of pleasure.

  “It’s okay if you need to answer that,” I say with a grin.

  Caitlin swallows while patting her lips with a napkin.

  “No, it’s just my best friend, Cammie. I told her that I was staying with you and now she’s freaking out. My phone is blowing up.”

  I chuckle.

  “Sounds like she’s a good friend.”

  “Oh, she’s the best. I’m lucky to know her.”

  “Were you going to stay with her if I didn’t come around?”

  Caitlin thinks for a moment. “Cammie offered, but she has three siblings. They live with her parents in a cramped two-bedroom apartment, so realistically, there was no space for me. The Forsters are really nice and would have found a way, but I didn’t want to put them out.”

  “Wow.”

  Cait nods.

  “Yeah. Cammie always came to my house for a reprieve from the chaos of her home, and I always went to her place when my stepmom got to be too much. It’s okay.”

  I put down my fork for a moment. “Well, you know that we have plenty of space. You could invite her over for a visit.”

  Caitlin shakes her head furiously. “Oh no, I don’t want to impose. It’s your mansion, and your private space. It’s too much to ask.”

  I grin. “Honey, you saw all the extra space I have. And I’m at work all day too. Your friend is welcome to come over. I’ll even lift the lingerie rule, so you can be clothed like a normal person. Is that what was holding you back?”

  She brightens and then giggles.

  “Yeah, sort of. I mean, Cammie and I are good friends, but she doesn’t want to see me in my bra and panties. We don’t have that kind of a relationship.”

  I laugh but then her phone buzzes again. “Maybe you should invite her for dinner tonight. After all, it seems like she’s freaking out and won’t stop calling,” I say while eyeing the phone meaningfully.

  “Really? Is that okay?” Cait says, her eyes bright.

  “Yeah definitely. I don’t want your friends to think you’re chained up in the basement or something. Although we can do that, if you’re interested.”

  Cait merely giggles.

  “Oh you!” But then she quickly picks up, squeals as she greets her friend, and invites her over before nodding and hanging up.

  “It’s done!” she announces. “You’ll be meeting Cammie later this week. She can’t wait either.”

  I raise an eyebrow at her.

  “Did you tell your friend about our arrangement?”

  “I did. I mentioned it in a text this morning. Is that okay?”

  “Of course. There are no secrets between us. Being discreet is different from having secrets, sweetheart. You know that.”

  Cait nods.

  “I know, I know, and Cammie’s not the judgmental type anyways. If anything, she’s really excited for me because she always thought I was way too boring and repressed. If anything, this is a huge step in the right direction.”

  I merely laugh, and to my surprise, my heart is light. It’s nice being here with Cait, enjoying a meal like a regular couple and sharing stories of ourselves. In fact, this feels a lot like a date.

  But then I stop myself. We’re not dating. This is a transaction, and not a genuine, traditional relationship. I brought Caitlin home specifically to satisfy my sexual needs, and I haven’t even done that yet. But looking across the table at the delectable girl, I vow to remedy that as soon as possible.

  7

  Travis

  * * *

  When we get back to my mansion after lunch, there’s a huge box on the doorstep. I look around.

  “That’s weird. Usually deliveries are taken to the back gate. But whatever. Let’s just bring it in.”

  “Oh my god, could it be my new clothes from the boutique?” Caitlin gasps, her eyes round. “But we were just there! Wow, Chantecaille’s delivery is fast.”

  I grin, heaving the box into my arms. It’s big, but not heavy.

  “Well, let’s see. Come on, honey. Let’s go inside and open it up. I want to see you model some of that lingerie.”

  She giggles, and after we enter, I put the box down in the foyer. Cait immediately begins tearing at the tape on the top. I have to laugh. It’s like Christmas for her, and her face is flushed as her eyes go wide with joy. But then she sits back with confusion on her heels.

  “Oh my God, Travis, what is all this?”

  Caitlin holds up a ream of fabric and I grin.

  “Our conversation got me thinking. While we were at the restaurant, I texted a concierge service I belong to. I had the Medina fabric store send over some fabric and a sewing machine. That’s all.”

  Cait’s eyes go wide.

  “Oh my God, you did this while we were at the restaurant?”

  I grin and nod.

  “Yep, while you were in the restroom.”

  Cait merely shakes her head in wonder.

  “You didn’t have to do this, Travis, and so soon too! I didn’t even know same-day delivery worked this fast!”

  I merely shake my head again.

  “No, it’s not same-day delivery, sweetheart. This is a special concierge service, so I pay a high price to get what I need within the hour. It costs a fortune, but seeing your happy expression is totally worth it.”

  She merely digs through the packaging again before standing up and shooting me a knowing smile.

  “Goodness, I thought you’d get me an old sewing machine, something I could fiddle with using the few clothes I brought with me. But this machine is brand new, Travis. It must have cost a fortune.”

  I merely shrug and grin again.

  “You deserve it, Caitlin. I want to see your dreams come true.”

  She bites her lip. “To be honest, I’m still not sure about my future, but I promise I’ll put this equipment to good use. I’ve never had a brand new sewing machine before, and it’s exciting because it has all the bells and whistles, including a magnetic seam guide and a slip reduction mat. Holy cow! This is top of the line, and I’ve never had anything close to this nice. Even the one Dad got me way back when was from a thrift shop.”

  My heart clenches a little, hearing about her past. But Cait doesn’t realize and continues to gush.

  “I can’t believe I have a sewing machine that won’t break all the time. No Fiona to tamper with it, and it’s not one of those ancient models I used at school. I can’t possibly thank you enough for this.”

  I take her hand.

  “It’s nothing. I hope you’ll make something for me.”

  She blushes. “Oh, not a chance. I’m not nearly good enough for that. Men’s clothes are actually very tricky. They look simple, but sometimes they can be more difficult to put together than women’s garments.”

  I don’t believe that for a second.

  “Are you sure, honey?”

  She laughs. “I know you were impressed by my drawings the other day, but I’ve only ever designed for women, I swear. I don’t know the first thing about making something for a man.”

  I smile and chuck her under the chin.

  “It doesn’t have to be anything major. I saw some drawings of button up shirts you did for women. Why not transform them into men’s shirts and make me one of those?”

  Caitlin thinks for a second. “I suppose it wouldn’t be that difficult, but I’ll need your measurements. After I’ve practiced a bit on this machine, of course. I can’t go in cold.”

  I smile.

  “I’m going to hold you to that.”

  Caitlin smiles up at me. “Good. I’d love to make you something, Travis, and I hope it turns out well. Of course, you don’t have to wear it if you hate it. It could be awful.”

  I shake my head.

  “You’re underestimating yourself, sweetheart. You’ve been sewing since you were a kid, a
nd I have no doubt it’ll be amazing, especially with this new gadget,” I say while patting the sewing machine.

  Cait smiles and continues to look through the fabrics I had sent over. Her eyes are bright and her manner assured. Clearly, my girl is humble but she knows what she’s doing.

  Then the curvy girl stands, and brushes herself off.

  “Thank you again, Travis. I’m going to be saying thank you for months, probably,” she says with an impish smile.

  “You don’t need to. The shirt will be thank you enough. But can I get a kiss, honey? That would make my day.”

  Caitlin’s eyes go wide because although she’s already been here a little over a day, I haven’t touched her yet. We had a spicy interlude in my study when she first arrived, but I haven’t put my foot to the pedal yet. Now, the time has come.

  Slowly, she leans in and my lips brush hers. She’s still for a moment before stepping a bit closer and tentatively putting her hands on my back.

  “Wind your arms around my neck, sweetheart,” I growl against her mouth. “Let me feel those big breasts against my chest.”

  Cait moans a bit, but she obeys, and this time, I kiss her hard and passionately. Oh shit, she’s so gorgeous and I’ve crave her so much. I need this woman, and I need her now.

  “Take off your clothes, honey,” I say gruffly.

  “What?” she asks, her voice dazed. “Right here?”

  “Yes, baby. It’s happening, and I need to see those lovely curves.”

  Slowly, Cait pulls herself away and unzips her dress. The filmy material puddles at her feet, leaving her in nothing but a tiny set of red lingerie. Fuck, I can see her nipples through the fabric and they’re blush pink and as hard as bullets.

  But I’ve become an animal. I can’t resist any longer, and without any warning, my hand slides down the front of her panties as I run my fingers up and down her moist slit.

  “Oh, God, that feels good,” Caitlin moans. She arches her back and presses her pussy against my hand. “I’ve never…”

  “I’ll treat you well, Caitlin. Don’t you worry. Just relax.”

  “I know, Travis,” she responds, breathless. “Yes.”

  I lift her and wrap her legs around my waist as we continue to kiss. The heat from her curvy body almost does me in, but I force myself to walk down the hall to the lower-level den. Then I kick the door closed behind us and drop her on a luxurious leather couch. She looks utterly beautiful, panting and breathless with her nipples hard and a wet patch at her crotch.

  “Oh, Travis,” Caitlin moans. Her hand reaches to me to cup my hard-on through my jeans. My cock pulses against her touch and I let out a rough moan of my own, unable to control the growing hardness.

  Caitlin senses this and starts tugging at the hem of my shirt. I pull it off and then remove my pants, dressed now only in my boxers. My shaft is already huge, and the purple tip pokes through the waistband.

  “Oh my god, is that …?” she trails off, her eyes going wide.

  “Yes, sweetheart. It’s big and it’s all for you,” I say. But I know the curvy girl. She needs to be stretched out first before accepting my length, so I lean forward to kiss and suckle at her breasts through her bra. Caitlin writhes on the couch beneath me, panting hard while spreading her thighs.

  My hand finds her pussy lips once again. She presses her hips against me as I dip one finger inside her damp hole, and she lets out another whiny, breathless moan.

  Then, my finger slips further in, and as I suspected, there’s a slight barrier there. It’s flexible but so sexy, and I have to taste it. Slowly, I move down between her legs, pushing her knees up, and pull her panties to the side before sampling that moist slit.

  She cries out ecstatically, her bud huge and rigid beneath my tongue.

  “Oh my god, Travis!” she squeals. “Oh god, oh god!”

  But that’s not enough. I dip my head again, sliding my tongue into her wetness, and sure enough, her hymen’s there. Slowly, I lick it, tasting the very essence of Cait’s innocence. But she’s twisting and turning, juicing onto my tongue, and now more than ever, she’s ready to become a woman.

  Slowly, I move up her body again, nuzzling her neck before pressing a tender kiss to her mouth. Her lips are full and puffy, those brown eyes dazed with pleasure.

  “I need more,” Caitlin begs. “Please, Travis. Make me feel… I want to know what it feels like.”

  “You don’t have to beg, baby,” I whisper. “I’ll give you what you need.”

  This time, I slip her panties all the way off and throw my boxers to the ground before looking at this lush woman laid out before me. She’s everything I’ve ever dreamed of: nude, curvy, big breasts heaving, and so wet between the legs.

  Slowly, I line my tip up with her opening and begin pressing forward. Her eyes open wide and she grips my shoulders.

  “Oh, God, it’s too big! I’m going to be split in half!”

  “No, you can do it, baby. Just relax.”

  Her eyes squinch shut a bit, her breathing labored.

  “Good girl,” I croon in her ear, pressing forward again. “You’re doing great.” Ah fuck, she’s so tight and hot, and my balls raise, already ready to explode.

  “Oh Travis. Unnnh, you’re so big.”

  Whispering encouragement into her ear, I ease myself in slowly until there’s a slight barrier at my tip. Then, with one mighty thrust, I break through the wall, pushing all the way in.

  A rush of possession floods my veins. Caitlin is no longer a virgin. She belongs to me now.

  I wait a minute as Caitlin adjusts to my size.

  “Unnnh,” she moans deliriously. “Oh fuck.”

  I stay still, although it’s practically killing me. She’s tight, hot and so drenched that her hot honey is running down my balls.

  “You okay, baby?”

  Her eyes are wide and dazed as she looks back at me.

  “Yes, Travis. Give it to me. Hard and deep. Please.”

  Those are the words I need to hear, and I pull practically all the way out before plunging right back in. Caitlin lets out another deep moan, her breasts vibrating against my chest as she takes the pounding. I knew my girl could do it. She was built for pleasing a man, and her breasts bobble with each deep thrust, her pussy growing tighter and wetter as I give it to her good.

  Then, my thumb finds her sweet nub and turns in circles to add to the pleasure.

  “Holy fuuuuuuck. Oh God. Oh God. Don’t stop. Something’s happening. I think I’m going to…”

  Caitlin screams out as her cunt convulses around me. It’s sheer heaven. Her fluids thicken a bit and then gush mightily, drenching my rod in her wetness. It’s too much. With a roar, I bury myself in her pulsing folds and empty my load.

  “FUCK!” I cry out. “Oh shit!”

  I’m panting as I collapse on the wide couch. She pulses more as I continue to spray, filling her to the brim with my male essence. There’s so much that it literally drips back onto my balls, coating us both in a combination of gooey secretions. Finally, Cait raises her head a bit.

  “Is that what it’s always like?” she asks, her voice weak from a combination of delirium and exertion.

  “No. It’s even better,” I pant. Her eyes go wide.

  “Are you serious?”

  I merely grin, my body hardening again. “Get up on your hands and knees, and I’ll show you,” I say. Slowly, I pull out and the girl obeys. With satisfaction, I see that her folds look swollen and used, with a bit a come trickling from her hole. Gently, I press my mouth to it, licking up the jizz and cleaning her from behind.

  “Oh my god!” she cries, turning to look at me from over one shoulder. But I’m a nasty bastard and merely smile again before lining up at her wetness once more.

  “Just stay still, baby,” and with that, I plunge back inside her delicious twat.

  “Oh, oh, oh,” Caitlin moans with each push. “Fuck, that’s good. Unnnh!”

  “You like that?”

&
nbsp; “Yes, Travis,” she pants, her head dropping low as she takes the hard pounding. “Oh yes!”

  I slip a hand beneath her torso and begin to toy with her breasts. Her bra got lost somewhere and the huge orbs shudder and swing with the rhythm of our love. Suddenly, her fluids begin to thicken again and she tenses slightly.

  “Unnnnnnh!” my girl squeals, her cunt clutching me tight. “Fuck!”

  Caitlin continues to shout, pant, and scream as I fuck her thoroughly. She may have been a virgin only twenty minutes ago, but she’s showing just how much she’s picked up in a short amount of time. Good girl. I always knew I had a fast learner on my hands.

  It doesn’t take long for both of us to come again, and for the second time today, I fill her pussy with jizz.

  This time however, we collapse together, wrapped in each other’s arms. I kiss Caitlin slowly, passionately, and hold her tight to my chest. It feels right, and I stroke her curls as she drifts off to sleep, my shaft still buried deep inside.

  As we lay there, the sweet girl snuggles closer, one hand trailing over my chest. Then she murmurs something, and if I’m not mistaken, it’s my name.

  I stare down at her innocent face, her features so delicate and feminine. This feels right. It feels good, and rewarding, in addition to sexual. But that’s the problem: it’s only supposed to be about sex, and I force myself to hold back because Caitlin and I are not in a relationship. She gives, I take, and vice versa. This is just an exchange and tonight was no exception, no matter how right it feels.

  8

  Caitlin

  * * *

  The whir of my sewing machine sends a thrill up my spine. As promised, Travis turned one of the spare rooms in the mansion into my own personal sewing room. It’s gorgeous, with large white work tables, a custom shelving unit, and yellow and white plaid curtains that I made myself. I’ve already filled the closet with some of my creations, and it’s only been a month.