tagTransgender & CrossdressersA Surprising Landlady

A Surprising Landlady


I had moved to a new city two weeks ago, and I was already pretty sick of slumming in hotel rooms. I was pretty sure that my new employers were getting pretty sick of paying for them as well! I'd spent every evening since moving getting shown around tiny flats in various states of disrepair, and I was becoming resigned to taking some squalid bedsit. While drowning my sorrows one evening, my phone rang, showing an unknown number. I picked up.

"Hi is that Dave?" The voice was unfamiliar, and was soft and smoky.


"Hi my names Teresa Jefferies. You left me a voicemail a few days ago enquiring about the room I was advertising; sorry its taken me so long to return your call."

"That's no problem Ms. Jefferies; thanks for getting back to me."

"Please, call me Teresa!" She chuckled. "I'm wondering are you still looking? My person I had lined up to take the room has cancelled, and I'm looking to get someone else in as soon as possible."

"Sure I'm still interested. When's a good time for me to come around and view it?"

"How about right now? I've got nothing pressing."

"Wow OK great. No time like the present Teresa!"

She passed on the address, which turned out to be a very smart townhouse about twenty minutes from my hotel. I smartened up as best I could and made my way there. I knocked on the door, and after a few seconds a beautiful mature lady answered. She matched my 6 feet in height without wearing any heels, and her long brown hair curled around her shoulders, framing a lightly made-up face and twinkling blue eyes. If pressed, I would've guessed her age at about forty. She wore a floral summer dress, showing off a pair of shapely calves and a hint of her ample cleavage. When she saw me, her face broke out into a huge grin.

"Hi you must be Dave," she said, reaching out to shake my hand.

"Yes, hi Teresa. Thanks so much for your time!"

"No problem Dave; I've been looking for a suitable lodger for ages. Won't you come in?" I followed her down the hall and into the kitchen, noticing how her dress clung to her round arse like a second skin. I was entranced, and only snapped out of my admiring gaze with the offer of a cup of coffee and a seat at the kitchen table.

"I'll get straight to the point Dave." Teresa said, still beaming at me over her coffee. "I like having someone else to help fill the house. I think you might be that that person. I'm not sure if you're looking for a place of your own or somewhere to lodge, but you can take a look around and if you like what you see we can go from there. I'll show you the bedroom now, it's a good size and you have your own en-suite. You've got the run of the house as well, as long as you don't mind sharing it with some crusty old bird!"

"Well I wouldn't call you old by any stretch! And I'm shocked with your forthrightness. Everywhere else has looked for references and security checks. You trust me that much after a single phone-call and a meeting at your front door?"

"I've got a good feeling about you Dave. I like what's in front of me. I've learned to trust my instincts about people."

"Well I'm loving what I see so far. Why don't we take a look around?"

"Sure thing Hun."

It was difficult to keep my attention on the house with Teresa escorting me, but even so, my hopes plummeted as I saw more. The place was luxurious, and the bedroom was bigger than some of the flats I'd seen; there was no way I could afford this!

Finally we arrived back to the kitchen, and this time I was treated to a glass of red wine.

"So what do you think Dave? Is everything to your taste?"

"God yeah Teresa, its beautiful. How much are you looking for in terms of rent?"

"£250 a month including bills; Does that seem reasonable?"

I was taken aback; it was less than half of what anyone else in the city was looking for; Teresa must've noticed the look of shock on my face, and continued:

"I'm guessing you think I'm conning you, but that's really not the case. I make good money; I don't need a lodger, but as I said before, I like having someone around. As long as it's the right person. I think that's you Dave, I've thought so from the second I answered the door. The rooms yours if you want it"

A soft smile played over her lips as I mulled it over. There wasn't much to mull; I was heartily sick of my hotel and I couldn't think of a better place to live for a few months.

"You've got a deal Teresa! So where do I sign? Or do you do things old-fashioned, and seal the deal with a handshake?" I teased.

"A handshake is good for me Hun! I've a feeling that this is going to be the start of a beautiful friendship."

I couldn't help notice her huge tits bounce as we shook, and I really hoped she didn't notice my raging hard-on!

I moved in the next weekend, and over the next few weeks, we quickly settled into a comfortable rhythm with each other. Teresa worked in banking, and I rarely saw her in the morning, and half the time I was in work past eleven at night. But at least a couple of times every week, we'd share a bottle of wine over dinner and learn more about each other. I found out that she was 53 as opposed to the early forty's I'd originally estimated, and was divorced. I didn't push her on the subject of relationships, but I sensed a dirty streak running through her mind; occasionally she'd quip that she was on the hunt for something young and hung to satisfy her, but quickly laughed it off. Had I been less shy, I would've volunteered in a heartbeat; on more than one occasion, I'd wanked myself to sleep imagining Teresa in bed next to me, or even better with her being on top of me!

One Saturday after getting back from there gym, I headed into the kitchen for something to eat; the creak in the floorboard must've given me away, because in seconds I heard a shout from Teresa asking me to come out to the garden. I arrived out to find her laid out on a sun bed, soaking up the rays.

"Sorry to bother you Dave, would you mind putting some cream on my back? I don't want to burn."

"No problem Teresa." I replied, before grabbing the sun cream and making a start on her shoulders, sitting beside her.

"You'd be better off straddling me Dave. Don't worry, I won't mind!"

I did as I was asked, and started again on her shoulders, slowly massaging the oil into her soft skin. Teresa made small talk for a while, before arching her back and moaning softly:

"Mmmmmm Dave you've got magic hands. Don't stop Hun."

As I worked lower, I edged down her body until my crotch was resting on her gorgeous round arse. I'd had a raging erection since I started, and I'm sure she noticed. Teresa didn't say a word though, although I'm sure I felt her pressing up against me, which did nothing to help!

As I finished at the small of her back, she looked over her shoulder, the familiar soft smile on her lips.

"You should get yourself a drink and come out and join me Hun. This sun's delicious."

I agreed and disappeared to get us both something long and cool, before getting rid of my T-shirt and taking the lounger next to Teresa. My hard-on still hasn't quit, and was more than obvious through my shorts. I think I caught Teresa eyes on it more than that once, but she said nothing about it. After awhile, she decided to turn over, and took my breath away once again. Her large round breasts were barely covered in a tiny blue bikini that matched her eyes, and as my eyes travelled down her body, I took in the rather large bulge nestled in her bottoms, almost a mirror image of mine. I was shocked, but strangely not disgusted; in fact, I could barely take my eyes off her surprise. Again Teresa said nothing, but her smile told me she'd caught me ogling her again.

As I lay in bed that night, I thought about it again. Did Teresa have a cock? What was she, a shemale or a transsexual or something like that? As I pondered, I came to the realisation that I didn't care; nothing had changed between us, and if I was honest with myself, my cock had barely been soft since I'd seen her bulge that afternoon. I moaned her name softly, and barely needed to touch my dick before I came like a fountain.

A few days passed without me seeing much of my landlady, but every night ended with me moaning her name as I came. I got back from work after an early finish for once, and wandered into the kitchen to find Teresa bent over at the freezer, her round arse straining against a tight black skirt. It had ridden up nicely, and I could see an inch of toned thigh above her black stocking-tops. She turned and flashed me a saucy grin.

"You getting a good look Dave?" she quipped as she stood up. "I've got a hot date tonight. I've had my eyes on this guy for a while now and I want to impress. How do I look?"

I took her in slowly, relishing the chance to check her out with her permission; her long legs were encased in stockings and her tiny skirt, and she finished the outfit with a sheer white blouse, low-cut and showing off the tops of her fantastic tits. Her styled hair framed her face perfectly, and the tip of her tongue licked her plump red lips as she waited for my opinion.

"You look fantastic Teresa, he's one lucky guy!"

"Thanks Dave, that means a lot. Its good to know that I can still turn a young mans head. Why don't you go sit inside and we'll share some wine before I take off."

I relaxed on the couch after a long day at work before Teresa entered. She was still grinning mischievously as she set the wine down on the coffee table and stood in front of me.

"You really think I look good Dave?" She asked softly.

"Definitely Teresa!" I replied. "Any man would be a fool not to be impressed"

"You're so sweet Hun" she purred. I couldn't take my eyes off her, and watched as her hands ran over her body and down to the hem of her skirt.

"I'm really glad I impress you Dave. Let me show you what I do when I really want to impress a guy."

My eyes dropped from hers and were level with her crotch as she slowly slid her skirt up over her stockings-tops, then easing it over her hips. She was wearing a pair of black lace underwear; they were practically see-through, and I could see her very large penis nestled underneath them. It looked like she was completely smooth all over, and I was hypnotized. I couldn't take my eyes off her cock as it started growing beneath her knickers.

"I'm taking a gamble that this will impress you even more. Does it impress you Dave?" she whispered.

I didn't trust my voice, so just nodded, never taking my eyes off her big dick. It was stretching her lacy underwear to breaking point.

"That's good Dave, because I love what I see. Can you tell?"

Teresa moved a little closer, standing between my legs with her lace-covered pole inches from my face. I felt her long nails run softly through my hair as I looked back up at her, still smiling angelically down at me. Neither of us said a word for what felt like an eternity. Before I'd met Teresa, I always considered myself straight as an arrow, but now I couldn't imagine anywhere else I'd rather be. I leaned in and softly kissed the tip of her cock through the lace. And I loved it! I loved the musky smell of her dick. I loved the feel of the panties against my lips. I loved the sound of her breath quickening as I kissed her. And I loved the feel of her getting even harder.

I nuzzled against her lacy thong, planting kisses up and down her shaft as it kept growing, before I felt Teresa pull my head from her crotch.

"Mmmm Dave. That felt so nice Hun. Have you ever tasted cock before?" She whispered, looking down at me.

I shook my head as I ran my hands up her stockings.

"That's okay Hun. You look eager though; have you ever thought about it?"

I nodded as I felt her push forward, brushing her dick against my cheek.

"Have you been fantasising about your landlady? About her cock? Have you thought about it while you wank? Have you been jerking off thinking about me?"

I nodded again, feeling so depraved.

"Good boy. Show Teresa what you've been thinking about doing."

I moaned softly as I got to work, my hand slipping down to cradle her silky-smooth balls as I ran my tongue over her fat bellend. Her nails were still running through my hair, encouraging me rather than forcing me. As if she could keep me away! I couldn't wait anymore; I needed to feel her dick against my lips! I pulled her thong to one side and her beautiful fat cock sprang up, slapping against my cheek again. She must have been nearly nine inches long, and thicker than I could have imagined.

"Fuck Dave, look how hard you made me. I've wanted to share my secret with you as soon as you moved in. It wasn't until I saw you eying me up in the garden that I knew I could. Why don't you help me make up for lost time?"

I just nodded again, licking my lips as she moved closer to me again. Teresa held my head softly as she rubbed her fat purple bellend over my lips, giving me my first taste of salty precum. I groaned softly as my tongue flicked out against her meat, swirling around her angry bellend before she slowly started easing inside my mouth. It felt like heaven, this beautiful mature creature filling my mouth with her throbbing dick.

"Fuck Dave I'm too horny. It's been awhile since I've had a good lodger to take care of my needs. You look so good down there, so sexy. My cock loves your mouth."

I felt her keep pushing until I had nearly seven inches of her meat between my lips; my hands were on her gorgeous round arse, trying to take even more inside me, but instead I felt her slowly start fucking my mouth, nice and slow at first.

"Jesus Dave its so good..........Your mouth is making me throb..........Its so hard to go slow, but I don't want this to end..........Oooooo fuck yeah babe..........I never want this to end."

I managed to pull her cock from my mouth just long enough to reply "I don't either Teresa. I'm yours."

"That's what I wanted to hear Dave," she said with a smile "Now make me cum".

With that, she forced herself back in my mouth, all her carefulness gone.

"God Dave..........Take it..........Suck me good! I can already feel it welling up for you baby..........I haven't cum in days..........I've been saving it all up for you."

I was drooling at the thought, squeezing her balls as I opened wider, loving every second. Teresa was getting closer to getting all nine inches in my mouth, and I wanted it so bad. We were both moaning louder, her hands pushing me down on her cock.

"Oh shit Dave..........I'm so close..........I'm going to fill your mouth up..........give my baby boy some cream..........Is that what he wants?"

I nodded vigorously, still sucking hard and fast.

"Oh fuck baby, oh shit, I can't hold it..........I'm going to cum, I'm going to cum so hard!"

With a final thrust, I felt my mouth filling up. Her cum was so warm and salty, and there was so much of it. I eased some of her cock out in the hope of keeping it all, but even as I swallowed, some still escaped from the corner of my mouth. All I could hear was Teresa breathing heavily as she pulled her cock from my mouth.

"Darling that was fantastic..........You're a natural cocksucker..........You made me cum so hard!"

I just moaned softly, licking her still swollen dick clean, loving the taste.

"I'm so glad you like the taste Hun. Why not come up and share some with me?"

I stood slowly as my gorgeous mature landlady leaned in and kissed me softly, sucking my tongue into her mouth.

"I love the taste of warm cum, and its so nice to share" she whispered, before licking the trails of spunk off my cheeks and pulling me in for another long hot kiss. Her seed tasted even better when I tasted it on here tongue. We parted slowly before Teresa gave me a wicked smile.

"Now Dave, if this old lady is going to get what she really wants, then both of us are wearing far too many clothes"

My sexy shemale landlady slowly began kissing down my neck as I felt her fingers on my shirt, unbuttoning it with ease.

"Did you know I had you in my sights Dave?" she whispered as I felt her breath on my chest. "Did you know I was in need of a new fuck-toy? That mummy has been waiting for too long?"

I gasped as I felt her bite my nipple softly.

"As soon as you walked through the door, I had a hard-on for you. I wanted that sexy little straight arse all to myself". I moaned louder as I felt her tongue trailing down my stomach, and her fingers on my jeans.

"Baby, I wanted to take you over the kitchen table as soon as you walked in..........I wanted to make you my bitch. But I waited until I was sure. Until I was sure that you'd be as hard for me as I was for you"

I moaned even harder as I felt her fingers running up and down my cock, teasing me through my boxers. I watched as she tugged them down. Teresa grinned at me, and paid my throbbing dick no attention. Instead, she kissed down my legs, pulling my jeans and boxers all the way off so I stood naked and rock hard before her. Then I watched as she kissed my dick softly. Just once.

"Fuck Dave this looks so tasty. I'm going to have a lot of fun with this beautiful cock later. But first, I want you to lie back on the sofa..........lift your legs up in the air for me. Show me what a good boy you are."

I'd do whatever she asked of me. I laid back and watched as she ran her hands up and down my legs, licking her lips, pushing them back slightly so my arse was nicely exposed. I moaned even harder as she leaned in against me, her breath warm against my arsehole as she spoke.

"This virgin hole is going to be so tight Hun. I need to get it nice and wet".

I felt her tongue run down my arse-crack before she began to rim me softly, tickling my hot hole as she flicked her tongue over me. Fuck, it felt amazing, like nothing I've ever felt before. I moaned loudly, watching my cock twitch as the tip of her tongue slipped inside me for a second.

"Is this the first time you've ever have your arse played with Dave? I'm going to show you how good it can feel"

Hearing me groan in response, Teresa giggled before going back to work. She lapped at my hole like a puppy, gradually opening me up. I was in heaven, I was being used and I loved it. I wanted to beg her to keep going, but I didn't need to. I felt her hands spread my cheeks slightly and a sudden warmth as she snaked her long tongue inside my arsehole, spreading my cheeks further as her lips pressed against my hole. I was in heaven! I wanted to touch my dick so badly; just one touch would be enough to make me explode. But I knew that's not what Teresa wanted.

Panting slightly, Teresa stood over me, my legs resting on her shoulders as she smiled down at me, stroking my skin.

"Dave you've been amazing so far. There's just one more thing I want. One more thing I need. Do you want it too?"

As she spoke, she unbuttoned her blouse, exposing her beautiful big tits clad in a lacy black bra. I'd waited so long to get a good look, and they were better than I imagined; they were impossibly firm and round, and her stiff nipples poked out against the lace. I couldn't take my eyes off them.

"Mmmm my boy is a tit man is he? I bet you didn't realise you were a cock man as well until you met me?"

"Fuck no Teresa, but I couldn't imagine a better combination"

"I'm glad you agree Dave. Now what do you think I want next?"

"I think you want to fuck me Teresa." My cock jerked again at the thought. A clear stream of precum was running from my bellend, and neither of us had touched my dick apart from one kiss; I'd never been so turned on! Teresa licked her lips as she rubbed her cock between my ass cheeks.

"I think I want to fill you with my fat nine inch cock. That's all I've been thinking about for some time. Is that what my darling boy wants?"

I could feel her cock resting against my arsehole; it felt amazing, unbelievably warm against me.

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