Tessa's Role Playing

Tessa's role playing

Before I decided to get into the IT world, I was just another college student. Each semester another group of coeds filled classrooms and my sexual imagination, but one in particular stood out. I would soon befriend this amazing woman, named Tessa, and this is her story.

When we met, Tessa was a 20-year-old junior in college. Maybe it was her height that stood out, being about 5'7", or maybe the amazing legs that carried her beautiful self into the classroom. One day she arrived in our accounting class wearing yoga pants and a snug workout top. I can still remember her ample breasts pressed into that sports bra, making them look even more amazing than before. With her combined curves and flat stomach, she could pass as a fitness model. I stared from the back of the class, forever etching that sight into memory.

Three times a week I'd see her in class. One Monday she looked as bored as I was listening to a dry monotone of supply and demand curves. My opportunity was there and after class I strike up a conversation. Exchanging introductions, we walked across the quad towards our next classes, chatting before we veered off to different buildings. As we parted, she looked back with a smile and said, "See you Wednesday." I smiled back saying "See you then" as I turned and walked to my next class. That day I finally had a name to go with my fantasies. Ahh, Tessa.

Tessa was not only amazing, I soon discovered how friendly and open she was. Over the next few weeks, purely by chance, we kept running in to each other, both on and off campus. She was easy to speak to, always saying 'hi' with a big smile whenever she saw me. I soon asked her out. We started dating and hit it off really well. Like I mentioned earlier, she was a sexual object of my fantasies and that alone attracted me to her, but she was fun, intelligent, very sweet and was so easy to be with.

Now while making love with her, I suspected she was holding something back. She would make little comments when we were intimate, some slutty and some kinky. Then one day I was on top and she whispered in my ear, "Do you fuck all your girlfriends like this? Take me from behind!" I pull out and she jams the pillows under her pushing her ass in the air towards me. "Spank and tell me I'm a bad girl." She commands. Well, I'm not going to miss out on this. I give her a good crack on the ass cheek and she yelps. Back inside her I go as her hand moves to her clit and starts to message it as I pound away. "I'm a naughty girl, spank me again." Crack! She yelps and immediately orgasms.

Little did I know just how fantasy driven she could be...

It was early in our sexual relationship I discovered Tessa liked to role play. This was her hidden little secret. She has an outstanding imagination, and likes to act it out. It didn't take long for an unannounced invitation into that world of hers. Looking back, there was nothing at all bizarre mind you, just sexy and fun (spank me I'm a bad girl kind of fun) mixed in with some talk on the trashy side. Soon I discovered her role playing side. Let me tell you about a few.

The first time she went into character, my initiation I assume, we'd dated about 2 weeks. It was very mild but elaborate enough to determine if I was game or not. This was not spur of the moment, she planned this. Arriving to take her to dinner, she opens the door dressed in a blue satin corset, thong and thigh high stockings complete with red lace bows at the top. With a look of surprise on my face, mouth slightly open, I was a loss for words. She takes a step or two back, places her hands on her chest (a chest now sporting the most cleavage I have seen her display) and goes right into character.

I step into her apartment, close the door behind me and wait to see where this goes.

Donning an English accent and portraying a very flirty damsel in distress, she says, 'Oh, woodsman that comes calling upon my door...' She does a curtsy and gives me an amazing glance at her accentuated cleavage. I'd never seen her in a corset, and what an amazing sight it was. Straightening up and still in character, she continues. 'There is no one here to save me from the raiders traveling the roads.' She gestures towards the window, then brings her hands back together at her chest. 'Will you do the honor of protecting me, just for the night, whilst the danger passes? I have no coin to pay for your services... but perhaps a barter?' She moves her hand down and releases the top two hooks of her corset allowing it to open. 'Will you find this a fair trade for your services?' She unhooks another and another. With each release, her breasts push it farther open revealing more cleavage. She turns and I can do nothing but stare at her amazing tight ass as she walks towards the bedroom. Tessa continues, 'Good sir, I will await in my boudoir for your answer.' She glances back at me as she exits the living room. I soon made negotiation with the English maiden for my services that night...

Tessa's role playing became more elaborate and kinkier as our relationship continued...

I never knew when she was going to pull another scenario on me. I must say I loved the spontaneity of these little trysts.

One day she phoned, asking if I could come over right after work. She was baking something and wanted to let me try it out. "I'll have it ready about 5:30." She said knowing my schedule well. Of course, I didn't suspect anything, and fell into one of her kinkier role plays...

I arrived and knocked on the apartment door. I heard her call out "door's open, come in." I stepped into her living room but there was no smell of baking and she was not in the kitchen. Her bedroom door was cracked about a quarter the way open -- presumably so she could hear me from the living room. I called out "Tessa? It's just me."

She replied from the bedroom. "Just wait there... I'll be available, in just another, minute." She sounded like she was doing yoga or an exercise of some sort... the words coming out like she was short of breath. I heard a muffed moan or two and between breaths she called out, 'you can... come in now'.

I walked over, opening the bedroom door fully. There I find her naked on the bed. With one arm over her head, and the other resting on her stomach, she was still catching her breath. Sweat glistened on her breasts and face, her knees bent and slightly apart with her vulva splayed wide by at a large red dildo. It was now very evident what those moans were. She lowers her hand and gently strokes her neatly trimmed landing strip.

"My new toy arrived today. (breath) I wanted to try it out. (breath) Hope you don't mind coming second tonight. (Deep breath)" I immediately start getting undressed. She's watching me while I stare at her endorphin flushed face, wet with sweat. She gave me a huge smile as her breathing slows. She sees me looking between her legs then slides her hand lower until it reaches her clitoral hood. She gets my attention by telling me 'I want you to be my second fuck today. I'm just your dirty little sex toy that needs reclaiming. Next?' she whispers with a giggle.

I move to the bed, press her knees farther apart then reach between them grabbing hold of the dildo in order to pull it out of her. Holy shit, how did she get this thing in her? It's think and a lot longer than I am. She gives a gasp and her breath quivers as it slides out, finally exiting her. Goosebumps appear on her chest and arms as I drop it on the floor. It is now MY turn. I lift her legs and I slide right into her. The big dildo stretched her a little, leaving her feeling used and giving me an unexpected turn on. I never had sex with a woman soon after she had someone, or something, inside her.

Going into character, Tessa continues with a quiet slutty voice. "I was horny and needed a good fucking. You weren't available so I hope you don't mind that I started without you. I was a dirty little slut today. Do you like dirty little sluts?" I can feel her building up to another orgasm.

I straighten up more, take a wrist in each hand holding them down next to her head. I reply "I do like dirty little sluts. As long I get to have my turn. Don't you know that pussy belongs to me, don't you little slut?"

She then continues, "Nothing pleases me as much as when you reclaim me. Take back what is yours." Slightly out of character, she continues "I'm so sore... (deep breath), fuck! I can feel every inch of you."

Role playing the naughty girlfriend that fucks a stranger initially made me a little jealous, but as fantasies go, I learned to love it. Sometimes she would tell me what she let the stranger do to her, using the dildo as a surrogate. Tessa confided it left her feeling dirty and used and it was a real turn on for her. This first time left her physically sore, mostly from the dildo, but she was in a horny mood and was glad I was OK with it. I did let her know how much of a turn on it was to me.

She acted this one out many more times and I enjoyed each variation. Once she had me to sit outside her door until she finished, yelled 'NEXT' and I was to come in, drop money on the night stand and have my way with her. This was interesting because these times she let me do most anything to her. She loved to be dirty talked to, making her feel sluttier. She was just like a prostitute you pay for; you get anything you wanted. I called this one the 'college hooker needing cash' role play. I could tie her to the bed, spank her, blindfold and cum anywhere I wanted to on her. She liked not being in control and I really enjoyed being the one in control.

This led to her playing the sub. This was the kinkiest one up to this point. She asked to be tied to the bed, blindfolded and have the dildo used on her 'til she came, then leave it inside her. She then asked me to finish on her. I'd come on her chest or stomach and leave her tied up, exiting the bedroom for 5-10 minutes. I'd get a beer and wait outside her door listening to her struggle a little, but that was part of it for her. She never used the safe word. If she was up to it, after removing her toy I'd reclaim her while still tied. This I labeled the 'slave in training' play.

Tessa was always a fun fuck.